2-CB	2,5-dimethoxy-4-bromo-beta-phenylethylamine
4-OTHB	4-hydroxy-4,5,6,7-tetrahydro-benzofurane
4-OTHI	4-hydroxy-4,5,6,7-tetrahydro-indole
5-CT	5-carboxamido-tryptamine
5-HT	5-hydroxy-tryptamine = serotonin
5-HT_1Dalpha	previous name for 5-HT_1D receptor
5-HT_1Dbeta	previous name for non-rodent 5-HT_1B receptor
5-HT_2A	serotonin receptor responsible for psychoactive effects
8-OH-DPAT	8-OH-N,N-dipropylamino-tetraline, 5-HT_1A ligand
AA	amino acid
AC test	adenylate cyclase test (5-HT₁ activity)
ALEPH-2	2,5-dimethoxy-4-ethylthio-amphetamine
AMT	alpha-methyl-tryptamine
betaC	beta-carboline
BOC	tert-butyloxycarbonyl protecting group
benzhydrol	diphenyl-methanol
benzhydryl	diphenyl-methyl
bufotenine	5-hydroxy-dimethyl-tryptamine
Bz	benzyl group (C₆H₅CH₂-)
CAR test	Conditioned Avoidance Response test
DD test	Drug Discrimination test
DET	N,N-diethyl-tryptamine
DMA	2,5-dimethoxy-amphetamine
DMABA	dimethylaminobutyraldehyde
DMT	N,N-dimethyl-tryptamine
DOB	2,5-dimethoxy-4-bromo-amphetamine
DOI	2,5-dimethoxy-4-iodo-amphetamine
DOM	2,5-dimethoxy-4-methyl-amphetamine
ETA	4-ethylthio-amphetamine
IAA	indolyl acetic acid
II	3-methylene-4-oxo-2,3,4,5,6,7-hexahydro-benzofurane
III	3-dimethylaminoethyl-4,5,6,7-tetrahydro-benzofurane
IV	3-methylene-2,3-dihydro-indole
imine	Schiff base
IP accumulation test	inositol phosphate accumulation test (5-HT₂ activity)
MAO-A	monoamine oxidase-A (NE, 5-HT, tyramine, dopamine)
MAO-B	monoamine oxidase-B (PEA, tyramine, dopamine)
MAO-I	monoamine oxidase inhibitor
MDA	3,4-methylendioxy-amphetamine
MDMA	3,4-methylendioxy-N-methyl-amphetamine
MMDA	2-methoxy-4,5-methylendioxy-amphetamine
MT	N-methyltryptamine
MTA	4-methylthio-amphetamine
MTHPI	N-methyl-1,2,3,6-tetrahydropyrid-3-yl-indole
PCC	pyridinium chloro chromate
PEA	beta-phenyl-ethyl-amine
PIA	2-phenyl-isopropyl-amine, amphetamine
pipradol	(2-piperidyl)-diphenyl-methanol, (4-piperidyl)-benzhydrol, Meratran ®
PTC	phase transfer catalysis
Schiff base	imine
Speeter / Anthony method	tryptamine synthesis via indolylglyoxylamide
stomach fundus strip data	5-HT_2B (and 5-HT₃?)
T	tryptamine
TBA-HS	tetrabutylammonium hydrogen sulfate
TBA-Br	tetrabutylammonium bromide
TEBA-Cl	benzyltriethylammonium chloride
TH...	tetrahydro...
Z	benzyloxy-carbonyl protecting group

Field Description

F	Syntheses of final compounds given
S	Chemical synthesis given (analogs, precursors, precursor analogs)
B	Receptor binding data given
A	In vivo activity data given
D	Duplicate references, marked with "»"
No	Number of reference
R	Reference added with release no.
Sub	Submitted by: Lil = Lilienthal

References

Topic

Short Abstract

Abstract

Journal

Vol

Page

Year

First Author

Sub

PEA

difuranyl-DOB

bromo-benzodifuranyl-isopropylamine from tetrahydro compound

J. Med. Chem.

5148

1998

M. A. Parker

Lil

p-di-Me-hydroquinone

p-di-Me-hydroquinone from p-di-Me-phenol through Elbs persulfate oxidation, mechanism

J. Chem. Soc.

2303

1948

W. Baker

Lil

(alpha-Me) phenylethylhydrazines

phenylethyl / isopropyl-hydrazines from styrenes / propenylbenzenes, hydration to PIA / PEA

Ber.

904

1965

T. Kauffmann

Lil

trifluoromethyl-DMA

trifluoromethyl-DMA from DOI with 1. (CF₃CO)₂O in toluene 2. CClF₂COOMe, CuI, and KF in DMF 3. KOH in iPrOH

J. Med. Chem.

4346

1994

D. E. Nichols

Lil

dihydrofuranyl-DMA analogs

4-subst. dihydrofuranyl-DMA analogs, rat and hum. 5-HT_2A and _1A binding, rat drug discrimination, DOB analog is 20 times more active in drug discrimination

J. Med. Chem.

2953

1996

A. P. Monte

Lil

dihydrofuranyl DMA analogs

4-subst. dihydrofuranyl DMA analogs, rat 5-HT_2A binding and rat drug discrimination, DOB analog has the twice the activity of DOB in drug discrimination and the same binding affinity

J. Med. Chem.

276

1991

D. E. Nichols

Lil

(4,5)-dihydrofuranyl DMA analogs

(4,5)-dihydrofuranyl DMA analogs, MMDA-2, rat drug discrimination (LSD), less active than DOM

#265

J. Med. Chem.

302

1986

D. E. Nichols

Lil

(di-) hydrofuranyl mescaline analogs

(di)hydrofuranyl mescaline analogs and escaline, hum. 5-HT_2A, _2B, and _2C binding and rat drug discrimination

J. Med. Chem.

2997

1997

A. P. Monte

Lil

(2-COOH)(5-MeO)-benzofuran

(2-COOH)(5-MeO)-benzofuran from o-hydroxybenzaldehydes and ethyl bromomalonate

J. Am. Chem. Soc.

872

1951

S. Tanaka

Lil

benzofuran

benzofuran from o-hydroxybenzaldehyde with 1. Cl-acetic acid 2. Ac₂O, AcOH, NaOAc

Org. Synth. Coll. Vol.

251

A. W. Burgstahler

Lil

subst. 2-COOH-benzofuranes

subst. 2-COOH-benzofuranes from o-hydroxy-benzaldehydes / -benzophenones with 1. ethyl Br-acetate 2. Ac₂O, NaOAc

#10

Bull. Chem. Soc. Jpn.

2762

1983

T. Suzuki

Lil

DOM metabolites

DOM metabolites synthesis: N-Ac-DOM, 4-subst. DMA: CH₂OH, CHO, COOH. In a rat metabolism study DOM 8%, 4-CH₂OH-DMA 50%, 4-COOH-DMA 28% were found in urine samples. Following paper is on the next pages (page 158)

#11

J. Med. Chem.

156

1971

B. T. Ho

Lil

4-alkyl-DMA

4-alkyl-DMA synthesis, human activity, sheep umbilical artery strips contraction

#12

J. Med. Chem.

1201

1975

A. T. Shulgin

Lil

2,4,5-tri-MeO-PEA, electrolytic reduction

2,4,5-triMeO-PEA via different old routes, electrolytic reduction, self experiment

#13

Recl. Trav. Chim.

291

1931

M. P. J. M. Jansen

Lil

[ ¹²⁵ I]-DOI

[ ¹²⁵ I]-DOI from DMA in 6 steps, some [ ¹²⁵ I]-DOI radioligand binding data

#14

J. Med. Chem.

1988

R. A. Glennon

Lil

ALEPH-2

ALEPH-2 (= 4-ethylthio-DMA) binding to 5-HT_1A, 5-HT₂, GABA_A (GABA and benzodiazepine site) and some rat behavioural data, no explanation for putative anxiolytic effect

#15

Arch. Pharmacol.

354

579

1996

M. Reyes-Parada

Lil

naphtyl-ethylamines

2-(7-)MeO-naphtyl-isopropylamines

2-(7-)MeO-naphtyl-isopropylamines and ethylamines via naphtaldehydes and nitroethenes / nitropropenes

#311

J. Med. Chem.

2050

1995

M. Langlois

Lil

7-MeO-1-naphtyl-ethylamine, N-methylation

7-MeO-1-naphtyl-ethylamine from 7-MeO-naphtyl-1-acetic acid, N-methylation via trifluoroacetamide methylation with MeI, melatonine analogues

#321

J. Med. Chem.

3231

1994

P. Depreux

Lil

benzaldehydes

benzaldehydes from toluenes with ferrous sulphate and cupric acetate in high yields

#47

patent

4,146,582

1979

P. Maggioni

Lil

Duff arom. aldehyde synthesis

hexamethylenetetramine formylation

hexamethylenetetramine formylation of 2,4,5-trimethoxy-3-methyl-benzene and 2-hydroxy-4,5-dimethoxy-3-methyl-benzene, yield 58%, nitrostyrene with nitromethane, reduction with LiAlH₄ to PEA

#521

Chem. Pharm. Bull.

4170

1982

K. Matsuo

Lil

p-formylation with hexamethylenetetramine / TFA

p-formylation of subst. benzenes with hexamethylenetetramine / TFA, yields are moderately to good

#528

J. Org. Chem.

3972

1972

W. E. Smith

Lil

3-formyl-indole with hexamethylenetetramine / AcOH

formylation of indole with hexamethylenetetramine / AcOH, yield 25%

#529

J. Org. Chem.

4002

1973

A. Chatterjee

Lil

2-OH-3,4-diMe-benzaldehyde

2-OH-3,4-diMe-benzaldehyde from 2-OH-3,4-diMe-benzene with hexamethylenetetramine / AcOH, yield 33%

#535

J. Chem. Soc.

820

1953

W. Baker

Lil

phenolether cleavage

phenolic compounds

a high yield PTC phenolether cleavage procedure, many substrates

#63

Synth.

437

1985

S. Andersson

Lil

benzofuran tryptamine analogs

5-MeO-DMT and 5-MeO-alpha-Me-T benzofuran analogs, 3 - 6 times lower affinity to rat 5-HT_2A, 2 times lower to rat 5-HT_1A receptor

#16

J. Med. Chem.

2061

1992

Z. Tomaszewski

Lil

tryptamines w/o indole

DMT-2-COOR

DMT-2-COOR from 2-dimethylaminopropyl-acetoacetate and aniline

#17

Arch. Pharm.

311

954

1978

C. H. Brieskorn

Lil

tryptamine

tryptamine from 2-chloropropyl-acetoacetate or -malonate

#18

Synth.

335

1974

Cs. Szántay

Lil

5-OH-T

5-OH-T from BzO-aniline and phtalimidopropyl-acetoacetate (19% over all)

#19

J. Chem. Soc.

2919

1961

L. Bretherick

Lil

5-OH-T, 5,6-diOH-T

5-OH-T and 5,6-di-OH-T from alpha-dimethylamino-MeO-PEA with ferricyanide

#20

J. Chem. Soc.

1165

1954

J. Harley-Mason

Lil

alpha-dimethylamino-PEA

alpha-dimethylamino-PEA from nitrostyroles and Li-acetamide

#21

Angew. Chem.

542

1971

D. Seebach

Lil

various indoles and T

indoles and tryptamines from indolines from (alpha-dimethylamino-)PEA

#22

Bull. Soc. Chim. Fr.

1335

1966

M. Julia

Lil

5-MeO-T, 5-EtO-T

5-MeO/EtO-tryptamine from phenylhydrazines and aminobutyraldehyde acetal with ZnCl₂ (poor yield)

#23

Ann.

516

1935

T. Hoshino

Lil

tryptamine

tryptamine from phenylhydrazine and aminobutyraldehyde acetal with ZnCl₂ (45%)

#24

J. Chem. Soc.

270

1911

A. J. Ewins

Lil

7-MeO-T

7-MeO-tryptamine from MeO-phenylhydrazine and aminobutyraldehyde acetal with ZnCl₂, poor yield

#25

Ber.

2102

1930

E. Späth

Lil

4/7-MeO-T

4- / 6-MeO-tryptamine from MeO-phenylhydrazine and aminobutyraldehyde acetal with ZnCl₂ (30% 6-MeO-T)

#26

Ber.

120

1930

E. Späth

Lil

IAA

indolacetic acid from phenylhydrazine and dimethoxybutyrate with sulfuric acid (21%)

#27

J. Am. Chem. Soc.

73?

5155

1951

M. W. Bullock

Lil

tryptamines

tryptamine from phenylhydrazine and chlorobutyraldehyde in EtOH / H₂O (70%)

#28

146321h

1973

I. I. Grandberg

Lil

alpha,N-DMT

alpha,N-DMT from indolylacetone and methylamine with H₂, Pd/C, methods references for sec. amines

#29

Tet. Lett.

4183

1979

D. B. Repke

Lil

5-subst. tryptamines

tryptamines through Abramovich-Shapiro (formic acid) synthesis

#31

J. Med. Chem.

4307

1994

T. Güngör

Lil

subst. N,N-dialkyltryptamines

tryptamines through Abramovich-Shapiro synthesis (HCl / EtOH), quart.-methylation, demethylation or Batcho-Leimgruber indole synthesis, Speeter-Anthony tryptamine synthesis

#32

J. Med. Chem.

908

1982

T. B. Kline

Lil

(5-MeO)tryptamine

Abramovich-Shapiro tryptamine synthesis from 2-oxo-piperidine-3-carboxylates and anilines via 1-oxo-beta-carboline

#33

J. Am. Chem. Soc.

78?

4589

1956

R. A. Abramovich

Lil

1-R-tryptamines

many subst. tryptamines from indoleacetic acids

#34

Bull. Soc. Chim. Fr.

1411

1965

M. Julia

Lil

1-R-tryptamines

1-subst. tryptamines from anilines and bromo-acetoacetate

#35

Bull. Soc. Chim. Fr.

1051

1962

M. Julia

Lil

1-R-tryptamines

1-subst. tryptamines from anilines and bromo-acetoacetamides

#36

Bull. Soc. Chim. Fr.

1056

1962

M. Julia

Lil

1-R-tryptamines

1-subst. tryptamines from anilines and bromo-acetoacetamides and -bromo-acetoacetates or from bromoethylindole from tryptophol

#37

Bull. Soc. Chim. Fr.

1060

1962

M. Julia

Lil

ethyl 4-bromoacetoacetate

ethyl 4-bromoacetoacetate from ethyl acetoacetate and bromine

#38

J. Org. Chem.

346

1947

A. Burger

Lil

ethyl 4-bromoacetoacetate

ethyl 4-bromoacetoacetate from ethyl acetoacetate and bromine

#39

Ber.

1042

1896

M. Conrad

Lil

acetoacetamides

acetoacetamides from acetoacetamide, NaOEt, and alkyliodide

#40

Monatsh. Chem.

1907

H. Meyer

Lil

ethyl 4-bromoacetoacetate

ethyl 4-bromoacetoacetate from ethyl acetoacetate and bromine, reaction mechanism

#41

J. Am. Chem. Soc.?

1655

1937

M. S. Kharasch

Lil

alpha-MT

alpha-MT from Trp

#42

J. Het. Chem.

775

1976

D. B. Repke

Lil

subst. tryptamines

many, many tryptamines through Abramovich, indolylacetone reductive amination, indolylmagnesiumbromide, indolylcarbaldehyde and gramine with nitroalkanes, tryptamine acylation / LiAlH₄ reduction...

#43

J. Chem. Soc.

7165

1965

B. Heath-Brown

Lil

5-triazolo-N-Me-piperid-3-yl-indole and -DMT

5-triazolo-3-N-Me-piperidyl-indole and 5-triazolo-DMT through phenylhydrazine / aldehyde route, binding data for many 5-HT-receptors, poor binding to 5-HT₂

#245

Bioorg. Med. Chem. Lett.

1825

1996

F. Sternfeld

Lil

5-MeO-DMT via tryptophol

5-MeO-DMT via indole-3-acetonitrile, indole-3-acetic acid, ethyl ester, Na-reduction to tryptophol, with PBr₃ to bromide, with aqu. dimethylamine at 100°C to 5-MeO-DMT or from 5-MeO-trimethylammoniumiodide with 1. AgCl₂ 2. vacuum destillation, poor yields

#315

Bull. Chem. Soc. Jpn.

221

1963

T. Hoshino

Lil

DMT from indole-3-acetic acid or tryptophol

DMT from indole-3-acetic acid via ethyl ester, amide, LiAlH₄ reduction, NMT from tryptophol via bromide (yield 60%), very poor yield

#316

J. Am. Chem. Soc.

3668

1956

M. S. Fish

Lil

indolyl-3-acetic acid

indolyl-3-acetic acid from 1. phenylhydrazine and beta-cyano-propionacetal 2. hydrolyzation or from indole with diazoesters

#322

Can. J. Res. Sect. B

170

1935

R. W. Jackson

Lil

5-NO₂-T and 5-NH₂-T

5-NO₂-(N,N-dimethyl-)T and 5-NH₂-(N,N-dimethyl-)T from p-NO₂-phenylhydrazone and 4-Cl-butyraldehyde (R. Paul, Bull. Soc. Chim. 8, 911 1941 and 15, 197 1984), reaction with aqu. dimethylamine and sodium hydrosulfite reduction (yield 52%), poor yields

#304

J. Am. Chem. Soc.

75?

1877

1953

E. Shaw

Lil

dimethyltryptamines via hydrazine / butyraldehde

5-subst. dimethyltryptamine from phenylhydrazine and dimethylaminobutyraldehyde acetal with 4% H₂SO₄ "original paper"

#468

J. Org. Chem.

3738

1994

C. Chen

Lil

Trp decarboxylation

tryptamine

tryptamine from Trp in cyclohexanol with cyclohexanone catalyst (92%)

#44

Chem. Lett.

893

1986

M. Hashimoto

Lil

tryptamine

tryptamine from Trp with acetophenone (100%)

#45

Bull. Soc. Chim. Fr.

2523

1964

G. Chatelus

Lil

phenylhydrazines

4-alkyloxyphenylhydrazines

4-alkyloxyhydrazines from anilines, NaNO₂, and SnCl₂ / HCl

#48

99842u

1967

M. J. Monballu

Lil

4-alkyloxyphenylhydrazines

4-alkyloxyhydrazines from anilines, NaNO₂, sodium sulfite, Zn / acetic acid

#49

Ber.

1842

1892

J. Altschul

Lil

4-alkyloxyphenylhydrazines

4-EtO-phenylhydrazine through improved Altschul procedure (removing Na salts against decomposition)

#50

J. Prakt. Chem.

1918?

Lil

4-alkyloxyphenylhydrazines

4-nPrO-phenylhydrazine through Altschul procedure

#51

J. Prakt. Chem.

120

1945

Lil

4-alkyloxyphenylhydrazines

subst. phenylhydrazines from anisidines with stannous chloride

#52

Aust. J. Chem.

1361

1974

J. L. Frahn

Lil

4-MeO-phenylhydrazine, 4- / 5- / 7-MeO-indole

4-MeO-phenylhydrazine via SnCl₂ route, 4- / 5- / 7-MeO-indole

#110

J. Chem. Soc.

296

1924

K. G. Blaikie

Lil

4-MeO-phenylhydrazine

4-MeO-phenylhydrazine from aniline via SnCl₂ route at -25°C, high temperature sensitivity of the reaction

#469

Aust. J. Chem.

1361

1974

J. L. Frahn

Lil

DMABA acetals

chloro-butyraldehyde

4-chloro-butyraldehyde from 4-chloro-butyrylchloride with formic acid and ammonium hydroxide

#53

Tet. Lett.

8153

1998

K. M. Shamsuddin

Lil

dibutylaminobutyraldehyde acetal

dibutylamino-butyraldehyde diethylacetal from 4-dibutylamino-propylchloride, Mg, and triethoxymethane, yield 60%, detailed instructions

#54

J. Org. Chem.

1356

1953

D. Perrine

Lil

bromo-butyraldehyde

4-bromo butyraldehyde from THF, boron bromide, and pyridinium chlorochromate (PCC), yield 70%

#55

Heterocycles

163

1982

S. U. Kulkarni

Lil

dimethylaminobutyraldehyde acetal

4-dimethylamino-butyraldehyde diethylacetal from available 4-aminobutyraldehyde diethylacetal, formaldehyde, Ti(OiPr)₄, and NaBH₄, yield 92%

#56

Tet. Lett.

2401

1994

S. Bhattacharyya

Lil

bromo-butyraldehyde acetal

4-bromo-butyraldehyde acetal from: 1. 4-Bromobutyric acid, boran dimethylsulfide complex, PCC 2. acetalization

#57

J. Org. Chem. USSR (Engl.Transl.)

1873

1989

N. I. Bobrova

Lil

bromo-butyraldehyde acetal

4-bromo-butyraldehyde acetal from: 1. 4-Bromobutyric acid and boran dimethylsulfide complex 2. Swern oxidation (DMSO / oxalylchloride) 3. acetalization, no reaction details

#58

Tet. Lett.

685

1988

T. V. Lee

Lil

chloro-butanol

4-chloro-butanol from THF and HCl gas, yield 55%, detailed instructions

#59

Org. Synth. Coll. Vol.

571

1943

D. Starr

Lil

chloro-butanol

4-chloro-butanol from THF and HCl gas, yield 56%

#471

J. Am. Chem. Soc.

1595

1934

D. Starr

Lil

bromo-butanol

4-bromo-butanol from THF and HBr gas, yield 58%

#472

Helv. Chim. Acta

885

1978

P. C. Wälchli

Lil

modified Rosenmund reduction of acid chlorides using EtiPr₂N, pure Pd/C and H₂ in acetone

#473

Recl. Trav. Chim.

1323

1971

J. A. Peters

Lil

chloro-butyraldehyde

4-chloro-butyraldehyde acetals from 4-chloro butanol, yield 67%

#60

J. Chem. Soc. Perk. I

2353

1977

C. P. Forbes

Lil

bromo-butyraldehyde

4-bromo-butyraldehyde from: 1. THF with HBr 48%, yield 38% 2. PCC, yield 62%

#61

J. Org. Chem.

3230

1979

E. Vedejs

Lil

bromo-butyraldehyde acetal

4-bromo-butyraldehyde dimethylacetal from THF, bromotrimethylsilane, PCC, and trimethoxymethane, yield 34%, no details

#62

J. Org. Chem.

686

1992

B. M. Trost

Lil

PCC oxidation

PCC = pyridinium chlorochromate oxidation of alcohols to aldehydes, yields 78% - 100%

#467

Tet. Lett.

2647

1975

E. J. Corey

Lil

chloro-butyraldehyde

chloro butyraldehyde from gamma-butyrolactone via chlorobutyryl chloride with thionyl chloride and ZnCl₂, chlorobutyryl methylanilide with N-methylanilin, yield 75%, and chlorobutyryl chloride with LiAlH₄, yield 25%

#470

Bull. Chem. Soc. Jpn.

446

1963

Y. Ban

Lil

aminobutyraldehyde acetal, tryptamine, NMT, DMT

aminobutyraldehyde diethylacetal from acrolein via cyanpropionacetal, tryptamine from aminobutyraldehyde acetal and phenylhydrazine, N-methylation with MeI and purification via benzoylation / hydrolysis (NMT), AgCl₂ / vacuum heating (DMT)

#474

Can. J. Res.

32?

592

1932?

R. H. F. Manske

Lil

4-OH-tryptamines

4-OTHB

one of the most interesting papers, 4-OTHB from 1,3-cyclohexanedione and chloroacetaldehyde

#64

Het.

2313

1984

M. Matsumoto

Lil

4-OTHB

the corresponding patent for 4-OTHB preparation

#65

101

23319d

1984

M. Matsumoto

Lil

4-OTHB

the corresponding patent for 4-OTHB preparation

#66

patent

101,003

1984

M. Matsumoto

Lil

4-OTHI

the corresponding patent for 4-OTHI preparation

#67

101

23331b

1984

M. Matsumoto

Lil

4-OTHI

the corresponding patent for 4-OTHI preparation

#68

patent

101,004

1984

M. Matsumoto

Lil

4-OTHI

ammonolysis in H₂O, purification ?

#69

104

148736f

1986

K. Goto

Lil

4-OTHI

ammonolysis in H₂O, purification ?

#70

patent

60,228,457

K. Goto

Lil

4-OTHI

ammonolysis in H₂O, purification ?

#71

104

148737g

1986

K. Goto

Lil

4-OTHI

ammonolysis in H₂O, purification ?

#72

patent

60,228,456

K. Goto

Lil

4-OTHI

ammonolysis in H₂O, purification ?

#73

104

148738h

1986

K. Goto

Lil

4-OTHI

ammonolysis in H₂O, purification ?

#74

patent

60,228,455

K. Goto

Lil

4-OTHI

4-OTHB ammonolysis in polyol partial ethers, dehydrogenation, purification ?

#75

106

67111n

1987

S. Matsuno

Lil

4-OTHI

4-OTHB ammonolysis in polyol partial ethers, dehydrogenation, purification ?

#76

patent

61,180,768

S. Matsuno

Lil

4-OTHI

4-OTHB ammonolysis in polyol partial ethers, dehydrogenation, purification ?

#77

106

67112p

1987

S. Matsuno

Lil

4-OTHI

4-OTHB ammonolysis in polyol partial ethers, dehydrogenation, purification ?

#78

patent

61,180,767

S. Matsuno

Lil

4-OTHI

4-OTHI from 2-acetonyl-1,3-cyclohexanedione

#79

Ann.

655

1962

H. Stetter

Lil

4-OTHI

4-OTHI from 1,3-cyclohexanedione, 2-amino-ethanol, and catalyst

#80

Tet. Lett.

9203

1996

Y. Aoyagi

Lil

4-OTHI

4-OTHI from 1,3-cyclohexanedione, 2-amino-ethanol, and catalyst

#81

102

62078q

1985

Ube Industries

Lil

4-OTHI

4-OTHI from 1,3-cyclohexanedione, 2-amino-ethanol, and catalyst

#82

patent

59,144,758

Ube Industries

Lil

4-OTHI

4-OH-indole from 4-OTHI from 4-OTHB-3-carboxylic acid (with ammonium carbonate) from 1,3-cyclohexanedione and ethyl bromo pyruvate

#83

Recl. Trav. Chim.

109

287

1990

E. M. M. van den Berg

Lil

4-OTHI

4-OTHI from 4-OTHB-3-carboxylic 4-OTHI from 4-OTHB-3-carboxylic acid with ammonium salts

#84

101

7022w

1984

Lil

4-OTHI

4-OTHI from 4-OTHB-3-carboxylic 4-OTHI from 4-OTHB-3-carboxylic acid with ammonium salts

#85

patent

59 05,159 ?

Lil

4-OTHI

4-OTHB-3-carboxylic acid from 1,3-cyclohexanedione and bromo pyruvate or bromoacetaldehyde diethylacetal.

#86

Synth. Commun.

1635

1986

Kneen

Lil

4-OTHI

4-OTHI from cyclohexanedione and ethyl vinyl ether via electrolysis and ammonolysis with ammonium carbonate

#87

Chem. Lett.

1603

1980

S. Torii

Lil

4-OTHI

4-OTHI from 1,3-cyclohexandione + NH₃ / H₂O + acetic acid 1,2-dibromoethyl ester

#88

108

94379d

1988

K. Nagao

Lil

4-OTHI

4-OTHI from 1,3-cyclohexandione + NH₃ / H₂O + acetic acid 1,2-dibromoethyl ester

#89

patent

62,138,469

K. Nagao

Lil

4-OTHI

4-OTHI from 4-(2-pyrrolyl)-butyric acid

#90

81163w

1969

M. Julia

Lil

4-OTHI

4-OTHI from 1,3-cyclohexanedione and aminosugars

#91

J. Chem. Soc. Perk. I

1237

1974

A. G. Sánchez

Lil

4-OTHI

4-OTHI from 1,3-cyclohexanedione and aminoacetaldehyde dimethylacetal

#92

Chem. Commun.

1429

1968

J. M. Bobbitt

Lil

4-OTHI

4-OTHI from 1,3-cyclohexanedione and aminoacetaldehyde dimethylacetal

#93

J. Org. Chem.

3541

1968

J. M. Bobbitt

Lil

4-OH-indole

4-OH-indole from 4-OTHI dehydrogenation, synthesis of 4-OH-tryptamines

#94

J. Het. Chem.

1977

D. B. Repke

Lil

4-OH-indole

4-OH-indole from 4-OTHI dehydrogenation + some references

#95

J. Org. Chem.

1232

1971

W. A. Remers

Lil

4-OH-indole

4-OH-indole from 4-OTHI dehydrogenation

#96

103

215169t

1985

H. Fukumitsu

Lil

4-OH-indole

4-OH-indole from 4-OTHI dehydrogenation

#97

patent

60,152,462

H. Fukumitsu

Lil

4-OH-indole

4-OH-indole from 4-OTHI dehydrogenation

#98

107

236506y

1987

Nagao

Lil

4-OH-indole

4-OH-indole from 4-OTHI dehydrogenation

#99

patent

62 63,563

Nagao

Lil

4-OH-indole

4-OH-indole from 4-OTHI dehydrogenation

#100

Chem. Ber.

101

2605

1968

H. Plieninger

Lil

4-OH-indole

4-OH-indole from 4-OTHI dehydrogenation via halogenation with CuX₂ and dehydrohalogenation with Li₂CO₃ + LiX in DMF

#101

Het.

165

1985

M. Matsumoto

Lil

4-OH-tryptamines

4-AcO-indole to many 4-OH-tryptamines via glyoxylamides

#102

J. Het. Chem.

845

1982

D. B. Repke

Lil

4-OH-tryptamines

synthesis of 4-MeO-indole, reaction with 1-dimethylamino-2-nitroethylene, LAH reduction to tryptamines

#103

J. Het. Chem.

175

1981

D. B. Repke

Lil

4-subst. indoles

synthesis of 4-NH₂ / COOCH₃ / CH₃ / OH / MeO / BnO-indoles

#104

Het.

1119

1981

L. I. Kruse

Lil

4-OH-indole, 4-NH₂-indole

4-OH-indole and 4-NH₂-indole from 2,6-dinitro-toluene in 3 steps, overall yields ~65%

#105

Bull. Chem. Soc. Jpn.

3742

1989

H. Tanaka

Lil

4-OTHI

4-OTHI-2-COOEt-3-CH₂COOEt from 1,3-cyclohexanedione and isonitrosoketone with Zn, AcONa, AcOH, yield 36% (Knorr's reaction)

#106

115537k

1967

A. N. Kost

Lil

4-nitroindole

4-nitroindole from 2-methyl-3-nitroaniline

#107

Org. Synth. Coll. Vol.

493

1993

J. Bergmann

Lil

4-nitroindole

4-nitroindole from 2,6-dinitrotoluene

#108

Tet. Lett.

3665

1983

J. Bergmann

Lil

4-nitroindole

4-NO₂-indole, yield 57%, 4-NO₂-7-Me-indole, yield 41%, from (2-Me-) 6-methyl-3-nitroanilines with 1. trimethyl orthoformate, pTsOH 2. NaOEt, diethyl oxalate in DMF

#109

Tet.

6085

1990

J. Bergmann

Lil

4-MeO-phenylhydrazine, 4- / 5- / 7-MeO-indole

4-MeO-phenylhydrazine via SnCl₂ route, 4- / 5- / 7-MeO-indole via 2-NO₂-MeO-toluene, 2-NO₂-MeO-phenylpyruvuc acid, and indole-2-carboxylate

#110

J. Chem. Soc.

296

1924

K. G. Blaikie

Lil

4-aminoindole, indoles

Indoles, 4-aminoindole from indole (!)

#111

Chem. Pharm. Bull.

726

1981

M. Somei

Lil

4-subst. indoles

4-OH-indole from 4-aminoindole from 4-nitroindole from 2,6-dinitrotoluene

#112

Chem. Pharm. Bull.

3145

1981

M. Somei

Lil

II, III

synthesis of II and III

#113

Het.

2585

1994

A. Ojida

Lil

synthesis of II

#114

J. Org. Chem.

3960

1990

M. Aso

Lil

synthesis of II

#115

Het.

1993

M. Aso

Lil

synthesis of II

#116

Het.

1003

1190

M. Aso

Lil

propynyl sulfonium salt

prop-2-ynyl sulfonium salt (CHCCH₂S+R2 Cl-) preparation

#117

J. Chem. Soc.

1904

1996

G. D. Appleyard

Lil

propynyl sulfonium salt

prop-2-ynyl sulfonium salt (CHCCH₂S+R2 Cl-) preparation

#118

J. Chem. Soc. Chem. Commun.

534

1971

J. W. Batty

Lil

Mannich / Eschenmoser's salts

Mannich salts (Eschenmoser's salt, CH₂NR₂⁺ Cl ^- ) from amine, alcohol, aldehyde, and methyltrichlorosilane, cheap and nontoxic procedure

#119

Synth.

228

1986

C. Rochin

Lil

Mannich / Eschenmoser's salts

Mannich salts (Eschenmoser's salt, (CH₂)₃N ⁺ Cl ^- ) from tetramethylenediamine, and trimethylsilyl chloride

#497

J. Org. Chem.

524

1980

T. A. Bryson

Lil

4-iodo-IV (R = Bn, allyl), "ene"-reaction

4-iodo-IV (R = Bn, allyl) from o-iodo-N-allyl-N-R-anilines with zirconium reagent, "ene"-reaction with Eschenmoser's salts to N-Et₂ and N-"piperidyl"-tryptamines V.

#120

J. Am. Chem. Soc.

113

4685

1991

J. H. Tidwell

Lil

4-iodo-IV (R = Bn, allyl)

4-iodo-IV (R = Bn, allyl), same procedure

#121

J. Am. Chem. Soc.

116

11797

1994

J. H. Tidwell

Lil

4-iodo-IV (R = allyl, CO₂Et)

4-iodo-IV (R = allyl, CO₂Et), same procedure

#122

J. Org. Chem.

7164

1994

J. H. Tidwell

Lil

IV (R = SO₂Ph)

IV (R = SO₂Ph) via 4-bromo-N-propargyl-sulfanilide with tributylstannane / cat. AIBN, promising procedure

#123

J. Am. Chem. Soc.

110

4796

1988

D. L. Boger

Lil

IV (R = Ac)

IV (R = Ac) via o-Iodo-N-propargyl-acetanilide with CrCl₂ and cat. NiCl₂

#124

Tet. Lett.

1601

1994

D. M. Hodgson

Lil

IV (R = Ac, part of a mixture)

IV (R = Ac, part of a mixture) via o-bromo-N-allyl-acetanilide with tributylstannane / cat. AIBN

#125

Tet. Lett.

1988

J. P. Dittami

Lil

IV (R = Ac)

IV (R = Ac) via o-Iodo-N-allyl-acetanilide with Pd(OAc)₂ / PPh₃

#126

Tet. Lett.

4325

1988

D. Burns

Lil

IV (R = SO₂Ph)

IV (R = SO₂Ph) via 4-iodo-N-allyl-sulfanilide with Pd(OAc)₂

#127

J. Chem. Soc. Perk. I

1941

1993

T. Sakamoto

Lil

IV (R = SO₂Ph-4-Me)

IV (R = SO₂Ph-4-Me) via 2-isopropenyl-tosylanilide with Pd(OAc)₂

#128

J. Org. Chem.

3584

1996

R. C. Larock

Lil

4-OH-7-Me-indole

4-OH-7-Me-indole from 4-BzO-indole-2-COOEt via 7-formylation, 2-saponification, 2-decarboxylation, 7-reduction, and catalytic debenzylation, also many different reactions with 2,3-subst. 4-OH/BzO-indoles

#129

Helv. Chem. Acta

2411

1971

F. Seemann

Lil

3-subst. 4-OH-indoles

3-subst. 4-OH-indoles from OTHI-2-COOR through saponification, decarboxylation, and dehydration

#130

Z. Chem.

183

1966

S. Hauptmann

Lil

4-OH-indole-3-carbaldehyde

4-BzO/alkylO-indole-3-carbaldehyde from indole-3-carbaldehyde in one-pot with 1. thallium(III)-trifluoroacetate (TTFA) in TFA 2. I₂ and CuI in DMF 3. NaOalkyl / NaOBz, yields: MeO 86%, BzO 58%, EtO 50%, (4-OH-synth: Het. 24, 3065 1986 M. Somei)

#131

Het.

797

1984

M. Somei

Lil

4-OH-indole-3-carbaldehyde

4-OH-indole-3-carbaldehyde from indole-3-carbaldehyde in a one-pot synthesis with 1. thallium(III)-trifluoroacetate (TTFA) in TFA 2. CuSO₄ in DMF 3. H₂O, 120°C, yield 70%, no reaction details, melatonine from 1-OH-N-Ac-tryptamine, yield 86%, no details

#132

Het.

1855

1996

M. Somei

Lil

4-OH-indole-3-carbaldehyde

psilocin from indole-3-carbaldehyde, 4-BzO-indole-3-carbaldehyde (improved yield 72%), 3-acetonitrile (NaBH₄, NaCN, MeOH, HCONH₂), 3-ethylamine (LiAlH₄, Et₂O), 3-dimethylaminoethyl (NaCNBH₄, HCHO, yield 97%), psilocin (H₂, Pd/C), overall yield 50%

#133

Het.

451

1998

F. Yamada

Lil

4-H / Me / MeO / OAc / OSO₂CF₃-indoles

subst. indoles, e.g. 4-H- / -Me- / -MeO- / -OAc- / -OSO₂CF₃ / 5-Br-indoles, from N-tosyl-2-vinyl-anilines with tributylvinylstannan / (Ph₃P)₄Pd, from 2-Br-anilines from 2-Br-nitrobenzenes

#134

J. Org. Chem.

1170

1988

M. E. Krolski

Lil

2-Br-anisidine

2-Br-anisidine = 2-Br-4-MeO-aniline from anisidine with Br₂ / AcOH, yield 40%

#407

Tet.

6875

1992

A. J. Clark

Lil

2-Br-anisidine

2-Br-anisidine = 2-Br-4-MeO-aniline via 3-Br-phenol, 3-Br-4-NO₂-phenol, 2-Br-4-MeO-nitrobenzene, over all yield 35%

#408

Tet. Lett.

6389

1987

C. Wright

Lil

4-Cl-DMT

4-Cl-DMT from 4-Cl-indole via Speeter-Anthony synthesis

#476

Can. J. Chem.

2586?

1963

McKay

Lil

bufoviridine

bufoviridine = bufotenine-O-sulfate isolation and identification, TLC Rf and colour reactions for many related compounds

#237

Biochem. Pharmacol.

270

1959

V. Erspamer

Lil

4-NO₂- / NH₂- / Cl-tryptamines

4-NO₂- / NH₂- / Cl-(N,N-dimethyl-)tryptamines, N-substitutions as LSD analogs. chlorobutyraldehyde / hydrazines, Speeter / Anthony, catalytic hydrogenation or dithionite reduction of NO₂ to NH₂

#238

Can. J. Chem.

2585

1963

J. B. McKay

Lil

selenopsilocin

N1-seleno psilocin analog, 5-step synthesis, "strong binding with serotonergic sites", no details on binding data

#239

Het.

1737

1992

A. Dari

Lil

psilocin / psilocybin analogs

psilocin / psilocybin analogs: psilocybin phosphoryloxy position isomers, 4-OH-tryptamine O and N substitutions (O-alkyl, O-esters, O-sulfate), psilocybin N-substitution analogs, UV spectra, colour reactions

#240

Helv. Chim. Acta

2073

1959

F. Troxler

Lil

psilocin, bufotenine pK_A, part. coeff., NMR

psilocin, bufotenine: pK_A, part. coeff., solution NMR

#241

J. Med. Chem.

207

1981

G. P. Migliaccio

Lil

2'- ¹⁴ C- / N-Me- ¹⁴ C-psilocin metabolism

2'- ¹⁴ C- / N-Me- ¹⁴ C-psilocin synthesis, rat metabolism and excretion

#242

Biochem. Pharmacol.

261

1962

F. Kalberer

Lil

4 / 5-AcO / OH-, 6 / 7-OH-indoles

4- / 5-OH-indole via Nemitzescu synth. via 2-NO₂-6-/5-OH-benzaldehyde, acetoxy-2,beta-dinitrostyrene reduction with Fe / AcOH, 4-/5-Acetoxy-indole, 6-/7-OH-indole via 2-NO₂-4-/3-OH-toluene, 2-NO₂-4-/3-BzO-hippuric acid, 6-/7-BzO-indole-carboxylate

#402

J. Chem. Soc.

1605

1948

R. J. S. Beer

Lil

4-BzO-indole, 4-BzO-/5-MeO-/H-tryptamines

4-BzO-indole via improved Leimgruber-Batcho route, alpha-subst. 4-BzO-/5-MeO-/H-tryptamines via indolylnitroalkanes with 2-NO₂-propene /-butene, tryptamines with Ni₂B reduction

#403

J. Org. Chem.

4294

1986

D. H. Lloyd

Lil

psilocybin and psilocin extraction

psilocin and psilocybin extraction, UV and IR spectra, colour reactions, synthesis

#450

Helv. Chim. Acta

1557

1959

A. Hofmann

Lil

meridianines

meridianines (Br-subst. (2-aminopyrimid-4-yl)-4-OH-indoles) from the tunicate Aplidium meridianum

#198

J. Nat. Prod.

1130

1998

L. H. Franco

Lil

phenolic OH phosphorylation

Tyr-O-phosphate

O-phospho-Tyr from tyrosine with pyrophosphoric acid (from P₂O₅ and phosphoric acid) at 80°C for 24 h, pure product after precipitation, yield: 50% - 91%

#135

Synth.

1938

P. F. Alewood

Lil

aryl-/alkyl-phosphates

aryl- / alkyl-phosphates from phenols / alcohols with 1. POCl₃ 2. H₂O, 80°C, yields75% - 85%

#136

Synth.

704

1974

G. R. Owen

Lil

aryl-/alkyl-phosphates

aryl- / alkyl-phosphates from phenols / alcohols with pyrophosphoric acid (from P₂O5 and phosphoric acid), CCl₃CN / NEt₃ for non-reactive educts, no yields given

#137

Bull. Chem. Soc. Jpn.

1891

1981

H. Yamaguchi

Lil

alkyl-dichlorophosphates

alkyl-dichlorophosphates from alcohols with POCl₃ / NEt₃, quantitative yields

#138

Tet. Lett.

1167

1985

R. L. Magolda

Lil

aryl-dichlorophosphates

aryl-dichlorophosphates from phenols with POCl₃ / NEt₃ or pyridine, yields ~75%

#139

J. Chem. Soc.

575

1966

?. Pinkus

Lil

phenyl-dichlorophosphate

phenyl-dichlorophosphates from phenol with in POCl₃, yield 70%

#140

Chem. Pharm. Bull.

202

1973

T. Koizumi

Lil

nucleotides

nucleotides from nucleosides with 1. quinoline-8-phosphate (from 8-OH-quinoline and phosphoryl chloride, yield 70%), CuCl₂ in pyridine 2. acetic acid, yields 59% - 75%, lit. review

#141

Chem. Pharm. Bull.

2121

1977

H. Takaku

Lil

oligo nucleotides

oligonucleotides with phosphotriester method

#142

Can. J. Chem.

3004

1971

T. Neilson

Lil

oligo nucleotides

oligonucleotides with phosphotriester method

#143

Chem. Ber.

102

2362

1969

F. Eckstein

Lil

oligo nucleotides

oligonucleotides with phosphotriester method

#144

J. Org. Chem.

245

1973

J. C. Catlin

Lil

oligo nucleotides

oligonucleotides with phosphotriester method

#145

J. Am. Chem. Soc.

3350

1969

R. L. Letsinger

Lil

nucleoside-2',3'-cyclic phosphates

nucleoside-2',3'-cyclic phosphates with phosphotriester method, 5-Cl-1-Me-imidazole catalyst

#146

J. Chem. Soc. Perk. I

2513

1973

J. H. van Boom

Lil

nucleoside-2',3'-cyclic phosphates

nucleoside-2',3'-cyclic phosphates with phosphotriester method, (5-Cl-)1-Me-imidazole catalyst

#147

Nucleic. Acids Res.

2731

1976

J. H. van Boom

Lil

5-Cl-1-Et-2-Me-imidazole

reaction of phenyl-phosphoro-dichloridate with 4-NO₂-phenol and cat. 5-Cl-1-Et-2-Me-imidazole

#556

J. Chem. Soc. Chem. Commun.

802

1977

C. B. Reese

Lil

subst. 5-Cl-imidazoles

reaction of phenyl-phosphoro-dichloridate with riboses and cat. 5-Cl-1-Et-2-Me-imidazole or 5-Cl-1-Me-imidazole, no success with 2,6-lutidine or pyridine

#557

J. Chem. Soc. Chem. Commun.

869

1971

J. H. van Boom

Lil

POCl₃, 5-Cl-1-Et-2-Me-imidazole

subst. phenyl-phosphoro-dichloridate from phenol, POCl₃, and cat. 5-Cl-1-Et-2-Me-imidazole

#555

Synth.

136

1979

R. Arentzen

Lil

indoles

subst. indoles

subst. indoles from anilinoacetaldehyd acetals with trifluoroacetic anhydride from anilines and bromoacetaldehyde acetals

#148

J. Org. Chem.

778

1981

J. E. Nordlander

Lil

subst. indoles

subst. indoles from methylsulfonyl-anilinoacetaldehyde acetals with TiCl₄ from methylsulfonyl-aniline and bromoacetaldehyde acetal with NaH

#149

J. Org. Chem.

249

1984

R. J. Sundberg

Lil

1-carboxymethyl-3-propyl-indole

1-carboxymethyl-3-propyl-indole from N-carboxymethyl-N-(2-oxopentyl)-aniline with PPA from N-(2-oxopentyl)-aniline

#150

J. Chem. Soc. Perk. I

1986

T. Shono

Lil

5-F-indole, 5-F-DMT, 5-F-DET

5-F-indole, 5-F-DMT, 5-F-DET, 7-MeO-1-naphtyl-ethylamine, N-methylation via trifluoroacetamide methylation with MeI, melatonine analogs

#321

J. Med. Chem.

3231

1994

P. Depreux

Lil

5-F-6-Cl-indole, 5-HT_2C agonists, 1-isotryptamines

5-F-6-Cl-indole from subst. 2-Br-aniline via trifluoroacetanilide, 3-OH-2,3-dihydroindole with MeLi, t-BuLi, and chloracetaldehyde at -100°C, indole with 1. p-TsA 2. NaOH

#332

J. Med. Chem.

2762

1997

M. Bös

Lil

7-Me-, 5,7-dichloro-, 5-BzO-7-Me-, 5-MeO-indole

7-Me-, 5,7-dichloro-, 5-BzO-7-Me-, 5-MeO-indole via Japp-Klingemann / Fischer indole synth. from subst. anilines, characterization of intermediate phenylhydrazones or azoesters

#390

J. Chem. Soc.

7185

1965

B. Heath-Brown

Lil

5-MeO-, 5,6-diMeO-, 6-EtO-indole, 5-MeO-T, 5-MeO-ET

5-MeO-indole via Japp-Klingemann / Fischer indole synth. from p-anisidine, yield 40% over all, 5-MeO-T via Speeter-Anthony, 5-MeO-N-Et-T with 1. acetylchloride 2. LiAlH₄, 5,6-dimethoxy- and 6-EtO-indole from subst. 2-nitro-beta-nitrostyrenes

#391

Recl. Trav. Chim.

313

1961

T. Kralt

Lil

5-HexO-indole, 5-HexO-ET

5-HexO-N-Et-T from p-HexO-aniline via Japp-Klingemann / Fischer indole synth. and Speeter-Anthony tryptamine synth.

#392

11180a

1965

Lil

subst. indoles

subst.indoles from subst. anilines via 2-amino-chloroacetophenones with chloroacetonitrile, indoles with NaBH₄ in refluxing dioxane, 5-MeO-indole yield 36% over all

#393

J. Org. Chem.

578

1979

T. Sugasawa

Lil

subst. indoles

subst. indoles from subst. 2-Br-anilines, N-vinyl-pyrrolidone, triethylamine, tri-O-tolylphosphine, and Pd(III)acetate, yields 40 - 56%

#394

J. Het. Chem.

1555

1987

A. Kasahara

Lil

indole-2-carboxylate

indole-2-carboxylate from subst. 2-nitro-toluene via 2-nitro-phenylpyravate salt with diethyloxalate and potassium, indole-2-carboxylate with H₂ / Pt in AcOH, over all yield 49%

#395

Org. Synth. Coll. Vol.

567

1973

W. E. Noland

Lil

indole

indole from 2-Me-formanilide and potassium t-butoxide at up to 350°C, yield 79%

#396

Org. Synth. Coll. Vol.

479

F. T. Tyson

Lil

indole

indole from 2-Me-formanilide and potassium t-alkoxides, yield 79%, see ref. #0395

#397

J. Am. Chem. Soc.

2024

1941

F. T. Tyson

Lil

subst. indoles via Leimgruber-Batcho review

subst. indoles via Leimgruber-Batcho method, extensive review

#398

Het.

195

1984

R. D. Clark

Lil

5-MeO-indole from 5-Bz-O-indole, 5 subst. DMT

5-MeO-indole from 5-Bz-O-indole with 1. H₂, Pd/C 2. dimethylsulfat, 5 subst. DMT via Speeter-Anthony, 1-alkylation with MeI and sodium amide in liqu. ammonia

#400

J. Am. Chem. Soc.

1977

1958

F. Benington

Lil

6-subst.indoles

6-subst.indoles from 4-subst. nitro-anilines, 4-subst. indoles not possible(?)

#401

J. Org. Chem.

2066

1983

S. Raucher

Lil

4 / 5-AcO / OH-, 6 / 7-OH-indoles

#402

J. Chem. Soc.

1605

1948

R. J. S. Beer

Lil

5-MeO-indole, 5-MeO-tryptamine

5-MeO-indole via phenylpyruvate, see ref. #110, 5-MeO-tryptamine via 5-MeO-indolyl-MgI with MeI, 5-MeO-indolyl-acetonitril with chloro acetonitril, tryptamine with Na / EtOH

#403

Ann.

513

1934

H. Wieland

Lil

5-EtO-/-MeO-indole, 5-EtO-Trp

5-EtO-/-MeO-indole via phenylhydrazone, poor yields, 5-EtO-Trp via gramine / acetamidomalonate

#404

J. Chem. Soc.

2462

1951

H. N. Rydon

Lil

indolylacetic acid diethylamide

diethy indolylacetamide from indol, MeI, and diethyl chloro-acetamide, yield 63%

#405

Arch. Pharm.

275

506

1937

R. Wegler

Lil

7-Cl-4-OR-indoles

4-OEtCl-7-Cl-indole from 4-Cl-3-NO₂-phenol with 1. BrEtCl, yield 95% 2. vinyl-MgBr, yield 36%, 4-OR-3-COCF₃-indole from indole with TFA, yields 90%

#531

J. Med. Chem.

2007

1999

R. E. Mewshaw

Lil

7-R-indoles

7-Me/Br/Cl/F-indole from 2-subst. nitrobenzenes with vinyl-MgBr, yields 42 - 67%

#532

Tet. Lett.

2129

1989

G. Bartoli

Lil

indole-1-protecting groups

1- tert -butoxycarbonyl-, 1-phenoxycarbonyl-, 1-(trimethylsilylethoxy)carbonyl-, 1-benzyloxycarbonyl-indole

#553

Synth.

1992

A. C. Weedon

Lil

tryptamine N-methylation

METs

MEAs from methylamides or formylamines with LiAlH₄ and ethyl acetate

#46

Helv. Chim. Acta

1199

1966

R. Stauffer

Lil

N,N-dimethyltryptophan benzylester

N,N-dimethyltryptophan benzylester from tryptophan benzylester with formaline, acetic acid, and NaCNBH₄, yield 17%

#151

J. Med. Chem.

1269

1994

A. M. MacLeod

Lil

N,N-dimethyltryptamines

5-subst. N,N-dimethyltryptamines from tryptamines with formaline, acetic acid, and NaCNBH₄, yield 71% / 83%, p-CN-phenylhydrazine, Cl-butyraldehyde acetal reaction

#152

J. Med. Chem.

3023

1994

J. L. Castro

Lil

N,N-dimethyltryptamines

5-subst. N,N-dimethyltryptamines from tryptamines with formaline, acetic acid, and NaCNBH₄, p-subst. phenylhydrazines, Cl-butyraldehyde acetal reaction

#153

J. Med. Chem.

1529

1993

L. J. Street

Lil

N,N-dimethyltryptamines

5-subst. N,N-dimethyltryptamines from tryptamines with formaline, acetic acid, and NaCNBH₄, p-subst. phenylhydrazines, Cl-butyraldehyde acetal and N,N-dimetylaminobutyraldehde acetal reaction

#154

J. Med. Chem.

1799

1995

L. J. Street

Lil

N,N-dimethyltryptamines

5-subst. N,N-dimethyltryptamines from tryptamines with formaline, acetic acid, and NaCNBH₄, or from 1. benzaldehyde, NaCNBH₃, 2. Me₂SO₄ / K₂CO₃, 3. H₂, Pd/C. p-subst. phenylhydrazines, Cl-butyraldehyde acetal reactiOn

#155

J. Med. Chem.

3566

1995

R. C. Glen

Lil

methylamines

methylamines from amines with formaline, NaCNBH₄ in

#156

J. Org. Chem.

1673

1972

R. F. Borch

Lil

alkylamines

alkylamines frOm aldehydes / ketOnes and amines with NaBH(OAc)₃, alsO fOr acid sensitive grOups

#157

Tet. Lett.

5595

1990

A. F. Abdel-Magid

Lil

indoline sidereaction

indolines from indoles with NaBH₄ in acetic acid

#158

J. Am. Chem. Soc.

7812

1974

G. W. Gribble

Lil

NaBH₄ in acetic acid

sec. amine alkylation with NaBH₄ in acetic acid

#159

Synth.

766

1978

G. W. Gribble

Lil

NaBH₄ in trifluoroacetic acid

sec. amine alkylation with NaBH₄ in trifluoroacetic acid

#160

Synth.

709

1987

G. W. Gribble

Lil

N,N-dimethyl-indolylbicycloheptanamines

N,N-dimethyl-indolylbicycloheptanamines from amines with formaline, acetic acid, NaBHCN3, yield 83% - 90%

#161

Arch. Pharm.

327

1994

K. Rehse

Lil

tert. amines

tert. amines from quart. amine iodides with LiAlH₄ in THF, good yields

#162

J. Am. Chem. Soc.

4651

1960

A. C. Cope

Lil

5-tBu- and 5-cyclopentyltryptamine

5-alkyltryptamines as specific 5-HT_1D agonists: N-propylation (nPrI: 3% sec., 75% tert.), N-methylation (DMS: 11% tert., (BoC)₂O / LiAlH₄: 70%), tryptamines from hydrazines and phtalimidobutyraldehyde acetals, no 5-HT₂ binding data

#163

J. Med. Chem.

526

1999

Y.-C. Xu

Lil

methylamines ?

methylamines from amines with formaldehyde, Ti(OiPr)₄, and NaBH₄, high yields (4-dimethylamino-butyraldehyde diethylacetal from available 4-aminobutyraldehyde diethylacetal, yield 92%)

#56

Tet. Lett.

2401

1994

S. Bhattacharyya

Lil

methylamines

methylamines from amines with NaBH₄, ZnCl₂, and paraformaldehyde im CHCl₂, good yields

#203

Synth. Commun.

2061

1995

S. Bhattacharyya

Lil

7-MeO-1-naphtyl-ethylamine, N-methylation

7-MeO-1-naphtyl-ethylamine from 7-MeO-naphtyl-1-acetic acid, N-methylation via trifluoroacetamide methylation with MeI, melatonine analogues

#321

J. Med. Chem.

3231

1994

P. Depreux

Lil

PTC N-alkylation

2-COOR-indole 1-methylation, alkanoyl-indole reduction

2-COOR-1-Me-indole from 2-COOR-indole with methyl-p-toluenesulfonate, NaOH, tetrabutylammonium bromide in CH₂Cl₂, 3-alkyl-indoles from 3-alkanoylindoles with NaBH₄ / BF₃-Et₂O

#320

J. Med. Chem.

2694

1997

M. Lehr

Lil

PTC indole-1-sulfonylation

PTC indole-1-sulfonylation with TBA-HS, NaOH, and sulfonic acid chloride in H₂O / benzene, yields > 85%

#548

Synth.

136

1979

V. O. Illi

Lil

constrained tryptamines

dihydropyrano constr. tryptamines

dihydropyrano analogs of N-methyl-pyrrolidin-2-ylmethyl- and N-methyl-pyrrolidin-3-yl-indoles

#164

Tet. Lett.

1994

J. E. Macor

Lil

dihydropyrano constr. tryptamines

dihydropyrano analogs of (1-Me, N,N-di-Me-) tryptamines, rat 5-HT_1A (8-OH-DPAT), bovine _1D (serotonin), rat _2A (ketanserin, DOI), pig _2C (mesulergine) receptor binding data, IP accumulation data, some compounds have a higher activity than 5-HT

#326

J. Med. Chem.

3625

1992

J. E. Macor

Lil

5-subst.N-Me-pyrrolidinylmethyl-indole

5-subst. N-methyl-pyrrolidin-2-ylmethyl-indoles, 12-step synthesis

#165

Tet. Lett.

8011

1992

J. E. Macor

Lil

5-amino N-Me-pyrrolidinylmethyl-indole

N-methyl-pyrrolidin-2-ylmethyl-5-aminoindole with 2,5-dimethylpyrrole as amino protecting group

#166

J. Org. Chem.

7496

1994

J. E. Macor

Lil

5-MeO-constr.

N-methyl-pyrrolidin-2-ylmethyl-5-MeO-indole, binding data and PI turnover / ad.-cyclase test

#167

J. Med. Chem.

4503

1992

J. E. Macor

Lil

Z-Pro

Z-Pro with benzyloxycarbonylchloride

#168

Ber.

462

1958

W. Grassmann

Lil

Z-Pro

Z-amino acids with different reagents

#169

Synth.

958

1986

E. Wünsch

Lil

Z-Pro

Z-Pro with benzyloxycarbonylchloride

#170

J. Org. Chem.

2861

1988

E. J. Corey

Lil

Z-Pro

Z-Pro with benzyloxycarbonylchloride

#171

J. Org. Chem.

2861

1988

E. J. Corey

Lil

Z-Pro

Z-Pro with benzyloxycarbonylchloride

#172

J. Am. Chem. Soc.

5552

1954

A. Berger

Lil

RU-24969 derivative

tetrahydropyrrolopyridone synth, 5-HT_1A, _1B, _1C, _1D, and ₂ binding data including (nor-) RU-24969, food intake test, ad.-cyclase test

#173

J. Med. Chem.

2087

1990

J. E. Macor

Lil

subst. 2-amino-cyclopentyl/hexylindol

subst. 3-(2-amino-cyclopentyl / hexyl)-indoles via indolylmagnesiumbromide / magnesium cuprate

#174

Tet. Lett.

683

1996

J. Ezquerra

Lil

N,N-dimethyl-indolylbicycloheptanamines

(N,N-dialkyl-) indolylbicycloheptanamines receptor binding, low affinity 5-HT₂ antagonists

#175

Arch. Pharm.

326

893

1993

S. Elz

Lil

2-amino-indolyl-bicycloactane

9 amino-indolyl-bicycloactanes, rat 5-HT_2A (ketanserin) and _1A (8-OH-DPAT) binding data, weak ligands

#287

J. Med. Chem.

386

1990

M. F. Schlecht

Lil

3-tetrahydropyridin-3-ylindoles

5,N-subst. 3-tetrahydropyridin-3-ylindoles, 5-HT_1A and 5-HT_2A binding data

#176

Bioorg. Med. Chem. Lett

2963

1995

T. Dahlgren

Lil

different constr. subst. tryptamines

(subst.) MTHPI, 3-tetrahydropyridin-3-ylindoles 5-HT₁, _1A, ₂ binding data

#177

Life Sci.

1961

1987

E. W. Taylor

Lil

imidazolylmethylindole

imidazolylmethylindole from indolyl acetic acid and ethylendiamine

#178

Eur. J. Med. Chem.

941

1994

M. Verma

Lil

indolyl-cyclopropylamines

5-MeO- / 5-F- / 4-MeO-trans-2-(indol-3-yl)cyclopropylamines, rat 5-HT_1A, hum. 5-HT_2A, _2B, _2C binding data

#204

J. Med. Chem.

4995

1998

S. Vangveravong

Lil

5-triazolo-N-Me-piperid-3-yl-indole and -DMT

5-triazolo-N-Me-piperid-3-yl-indole and 5-triazolo-DMT through phenylhydrazine / aldehyde route, binding data for many 5-HT-receptors, poor binding to 5-HT₂

#245

Bioorg. Med. Chem. Lett.

1825

1996

F. Sternfeld

Lil

3-(pyrrrolidin-3-yl)indoles

N-, 5-, 6-subst. 3-(pyrrrolidin-3-yl)indoles from 1. indoles and succinimides in AcOH 2. LiAlH₄ reduction

#309

Synthesis

443

1997

J. E. Macor

Lil

pyrrrolidinyl-indole, N-Me-pyrrolidinylmethyl-indole

5-nitropyridylamino subst. N-methyl-pyrrolidin-2-ylmethyl- and N-methyl-pyrrolidin-3-yl-indoles, 5-HT_1A and _1D binding and activity (AC inhibition) data

#310

J. Med. Chem.

2509

1994

J. E. Macor

Lil

methylamino-cyclohexyl/cyclopentyl-indoles

(N-Me-) 3-(2-methylamino-cyclohexyl/cyclopentyl)-5-MeO-indoles, no binding to 5-HT receptors detectable

#312

Heterocycles

1497

1990

J. E. Macor

Lil

3-piperidylmethyl-indoles

5-OH-3-piperidymethyl-lindoles from indole-MgBr and chloromethylpyridine (in a weakly polar solvent for 3-specifity), pyridine-N methylation for N-methyl derivatives, an catalytic hydrogenation

#313

Arch. Pharm.

308

209

1975

E. Friderichs

Lil

3-piperidylindoles

5-OH-3-piperidyl-indoles via 3-pyridylindoles (via Fischer indole synthesis, method of ref. #306), pyridine-N methylation for N-methyl derivatives, NaBH₄ reduction to tetrahydropyridin, and catalytic hydrogenation

#314

Arch. Pharm.

308

663

1975

E. Friderichs

Lil

5,N-subst. alpha-4 methylene bridged tryptamines

5, N-subst. alpha/4 methylene bridged tryptamines, rat 5-HT₁ (5-HT) and 5-HT₂ (spiperone) binding data, some have good 5-HT₂ binding affinities (antagonist labeled!)

#334

J. Med. Chem.

1746

1988

M. E. Flaugh

Lil

amino-carboxamido-tetrahydrocarbazole

3-amino-6-carboxamido-1,2,3,4-tetrahydrocarbazole, 5-HT_1A, _2C, _1D, and _2A receptor binding data

#336

J. Med. Chem.

1918

1993

F. D. King

Lil

dihydropyrano constr. DMT

dihydropyrano analogs of N,N-di-Me-tryptamine synthesis

#399

Tet. Lett.

1039

1992

J. E. Macor

Lil

2-alpha- and 2,beta-ethylen brigded 5-MeO-T

2-alpha- and 2,beta-ethylene and -propylene bridged 5-MeO-tryptamines

#406

J. Med. Chem.

451

1998

D. J. Davies

Lil

5-subst. 3-piperidylindole-2-COOR and DMT-2-COOR

5-subst. 3-piperidylindoles-2-COOR and DMT-2-COOR from anilines and subst. acetoacetate from acetoacetate, NaOEt, and dimethylaminopropyl chloride

#475

J. Med. Chem.

2347

1997

G. P. Moloney

Lil

peduncularine

peduncularine (indolylmethyl-azabicycloocten) synthesis via phenylhydrazine and alkyl acetal in 4% H₂SO₄, yield 32%

#554

J. Am. Chem. Soc.

111

2588

1989

W. J. Klaver

Lil

open-ring tryptamines

subst. 2-(3-amino-1-oxopropyl)-anilines

subst. 2-(3-amino-1-oxopropyl)-anilines, rat fundus strip data, all substances are agonists

#179

Drug Res.

515

1983

W. Back

Lil

5-MeO-2-(3-dimethylamino-1-oxo-propyl)-aniline

5-MeO-2-(3-dimethylamino-1-oxopropyl)-aniline, phenylpiperazine and bezoylpiperazine subst. amphetamine analogs, rat 5-HT₁ (5-HT) and ₂ (ketanserin) binding data, rat drug discrimination data (TFMPP, DOM), all have higher affinity for 5-HT₁ (aniline 24x)

#327

J. Med. Chem.

630

1986

R. A. Lyon

Lil

reductions / hydrogenations

sodium dithionite

reductive alkylation with sodium dithionite (Na₂S₂O₄), yield 68% (dicyclohexylamine)

#180

Aust. J. Chem.

201

1979

P. M. Pojer

Lil

Pd/C, formic acid

catalytic hydrogenation with in sity H₂ generation from formic acid (1-azido-3-indolyl-aceton), indole grignard reaction

#181

J. Het. Chem.

469

1988

J. P. Sanchez

Lil

nitropropene reduction

NaBH₄ / NiCl₂ reduction of 1-nitrocyclohexene to cyclohexylamine, isolated yield 66%, rection yield maybe higher

#182

Tet. Lett.

6413

1985

J. O. Osby

Lil

2,4,5-triMeO-PEA, electrolytic reduction

2,4,5-triMeO-PEA via different old routes, electrolytic reduction, self experiment

#13

Recl. Trav. Chim.

291

1931

M. P. J. M. Jansen

Lili

nitrostyrene Zn-Hg / HCl reduction

2-EtO/PrO-3-MeO-nitrostyrene reduction to PEA with Zn-Hg / HCl, yield 60% / 52%, 3,4-methylendioxy-benzylcyanide reduction with H₂ / EtOH / Raney-Ni / NH₃, yield 58%

#534

Bull. Soc. Chim.

231

1960

R. Delaby

Lil

nitrostyrene Zn-Hg / HCl reduction

3-Br-4-OCO₂Et-(5MeO-)nitrostyrene reduction to 3-Br-4-OCO₂Et-(5MeO-)PEA with Zn-Hg / HCl, yield 63% (65%)

#522

Arch. Pharm.

322

477

1989

P. Pachaly

Lil

nitrostyrene NaBH₄ / Me₃SiCl reduction

2,3,4-trimethoxy-nitrostyrene reduction to PEA with NaBH₄ / Me₃SiCl, aminoalcohols from AA, prim., sec., tert. amines from amides, amine from cyano, yields > 90%

#523

Angew. Chem.

101

220

1989

A. Giannis

Lil

nitrostyrene electrolytical reduction

2-Br-3,4-diMeO-nitrostyrene electrolytical reduction to 2-Br-3,4-diMeO-PEA, yield 50%, nitrostyrene from aldehyde with nitromethane

#524

Chem. Pharm. Bull.

1491

1963

K. Bessho

Lil

nitroalkene reductions to amines and hydroxylamines

nitroalkenes (incl. 3,4-diMeO-phenyl-nitropropene) reductions to amines with BH₃-THF / cat. NaBH₄ in THF for 6 d, yields 85 - 91%, with NaBH₄ / BF₃-Et₂O in THF, yields 74 - 79%, reductions to hydroxylamines with BH₃-THF / cat. NaBH₄ or NaBH₄ / BF₃-Et₂O, yields 74 - 79%, reductions to nitroalkanes

#525

Tet.

7443

1990

G. W. Kabalka

Lil

nitroalkene reductions to amines

nitroalkenes (incl. 3,4-diMeO-phenyl-nitropropene) reductions to amines with BH₃-THF / cat. NaBH₄ in THF for 6 d, yields 85 - 91%

#526

Synth. Comm.

1099

1984

M. S. Mourad

Lil

nitroalkene reductions to nitroalkanes

nitroalkenes (incl. 3,4-diMeO-phenyl-nitropropene) reductions to nitroalkanes with trialkyl borohydrides, yields 65 - 81%

#527

Synth. Comm.

1093

1984

R. S. Varma

Lil

nitrostyrene reduction with H₂ / Pd / AcOH / H₂SO₄

3,4-methylenedioxy-nitrostyrene reduction to PEA with H₂ / Pd / AcOH / H₂SO₄, yield 93%

#550

Ber.

1579

1935

O. Schales

Lil

nitrostyrene reduction with H₂ / Pd / AcOH / H₂SO₄

2-OH-, 3-OH-, 3-MeO-4-OH-, and 4-OH-nitrostyrenes from benzaldehydes and reduction to PEA with H₂ / Pd / AcOH / H₂SO₄, yields 67 - 85%

#551

Ber.

2154

1938

G. Hahn

Lil

nitrostyrene reduction with Zn-Hg / HCl

3,4-methylenedioxy-5-Br- and 3-MeO-4-EtOCO₂-nitrostyrene reduction to PEA with Zn-Hg / HCl / EtOH, yields 81% and 56%

#552

Chem. Pharm. Bull.

217

1968

M. Tomita

Lil

nitrobenzene reduction with SnCl₂

subst. nitrobenzene reduction to anilines with SnCl₂, yields > 91%, erratum: #542

#541

Tet. Lett.

839

1984

F. D. Bellamy

Lil

nitrobenzene reduction with SnCl₂

erratum to #541

#542

Tet. Lett.

1362

1985

F. D. Bellamy

Lil

red. alkylation with NaBH₄ in H₂O

various red. alkylations of acetaldehyde, benzaldehyde, acetone, and cyclohexanone with lysine esters, anilines, and alkylamines with NaBH₄ in aqueous solution

#549

J. Org.Chem?

3259

1963

K. A. Schellenberg

Lil

N,N-dimethyl-Trp

bromomalonates

bromomalonates and bromomethylmalonates with CuBr₂

#183

Chem. Lett.

1091

1998

Y. Suzuki

Lil

bromomalonates

bromomalonates from malonic acid with 1. alcohol / HCl gas 2. Br₂, yield 86%

#184

J. Org. Chem. USSR (Engl.Transl.)

1042

1994

P. M. Kochergin

Lil

dimethylamino-malonate

ethyl dimethylamino-malonate from dimethylamine in EtOH and ethyl bromomalonate (Org. Synth. Coll. Vol. 1, 245 1941 Palmer)

#185

J. Chem. Soc.

547

1949

E. R. H. Jones

Lil

dimethylamino-malonate

methyl dimethylamino-malonate from dimethylamine in MeOH and methyl bromomalonate, yield 76%

#186

Coll. Czech. Chem. Comm.

1980

V. Král

Lil

dipropylamino-malonate

ethyl dipropylamino-malonate from dipropylamine and ethyl bromomalonate in THF, yield 85%

#187

J. Med. Chem.

1076

1992

M. W. Moon

Lil

(5-OH)-N,N-dimethyl-Trp

(5-OH)-N,N-dimethyl-Trp from gramines and ethyl dimethylamino-malonate with 1. NaOH, benzene 2. Ba(OH)₂, MeOH 3. H₂O, Na₂SO₄

#188

Ann. Chem. (Rome)

1037

1958

S. Corsano

Lil

N-terminal substitutions

2-CB and 5-MeO-T derivatives

38 mainly N-substituted-benzyl 2-CB and 5-MeO-T derivatives, hum. 5-HT_2A (ketanserin), _2A (DOI), and rat _2C binding data, some seem to be potent agonists

#190

J. Med. Chem.

1929

1994

R. A. Glennon

Lil

5-MeO-N-Me-N-indolylmethyl-tryptamine

5-MeO-N-Me-N-indolylmethyl-tryptamine isolation from Antirhea lucida

#540

Planta Med.

569

1995

B. Weniger

Lil

QSAR

hallucinogenic PEA QSAR

49 2,4,5- and 3,4,5 subst. PEA in a (MTD-) QSAR study

#191

Quant. Struct.-Act. Relat.

459

1997

M. Mracec

Lil

hallucinogenic PEA and tryptamines QSAR

66 subst. PEA and tryptamines in a CoMFA-QSAR study

#192

Quant. Struct.-Act. Relat.

447

1997

G. Beuerle

Lil

hallucinogenic PEA QSAR

92 subst. PEA in a QSAR study

#274

J. Med. Chem.

3845

1998

B. W. Clare

Lil

5-HT reuptake inhibitor pharmacophore

5-HT reuptake inhibitor pharmacophoric model

#429

Pharm. Acta Helv.

235

1994

A. Rupp

Lil

various reactions

Arylbromide methoxy substitution

Cu(I) / ester catalyzed MeO-benzenes from Br-benzenes and MeONa

#193

Tet. Lett.

1007

1993

P. Capdevielle

Lil

N-methyl-N-formyl-1-Cl-isopropylamine

N-methyl-N-formyl-1-Cl-isopropylamine from N-formyl-alanine with 1. LiAlH₄ 2. formamide 3. thionyl chloride

#199

J. Chem. Soc.

858

1957

A. H. Beckett

Lil

methylendioxybenzenes

methylendioxybenzenes from catechols and DCM or CH₂BrCl with CsCO₃ in DMF or acetonitrile, yields > 86%

#194

Tet. Lett.

2461

1991

R. E. Zelle

Lil

2-OH-4,5-diMeO-benzaldehyde

2-OH-4,5-diMeO-benzaldehyde from 3,4-diMeO-benzaldehyde with m-Cl-perbenzoic acid (MCPBA)

#195

J. Chem. Soc. Perk. I

1435

1996

K. Chiba

Lil

N-alkyl-N-acetyl-anilines

N-alkyl-N-acetyl-anilines from N-acetyl-anilines, alkylating agent, and PTC (TEBA), yields 82% - 95%

#202

Synth.

113

1976

R. Brehme

Lil

indole oxidation

5-oR-tryptamines and -tryptophanes

5-MeO and 5-OH-tryptamines and -tryptophans from tryptamine and tryptophan in good yields

#196

Chem. Pharm. Bull.

2544

1984

M. Taniguchi

Lil

1-OH-tryptamine-amides

1-OH-tryptamine-amides and 1-OH-DMT from tryptamine-amides and DMT with 1. triethylsilane in CF₃COOH, yield 92% 2. Na₂WO₄*2H₂O, yield 55% - 72%, no details given

#200

Het.

119

1995

M. Somei

Lil

1-OH-tryptamine-amides

5-MeO-N-acetyl-tryptophan-methylester from 1-OH-N-acetyl-tryptophan-methylester with H₂SO₄ / MeOH, yield 71%, no details given

#201

Het.

1859

1993

M. Somei

Lil

indazoles

tryptamine indazole analog

tryptamine indazole analog, lengthly synthesis, pharmacological activities compared to tryptamine

#218

J. Am. Chem. Soc.

5242

1957

C. Ainsworth

Lil

5-HT indazole analog

5-HT indazole analog, lengthly synthesis, activities compared to 5-HT: on rat uterus 50%, guinea pig ileum 80%

#213

J. Am. Chem. Soc.

5245

1957

C. Ainsworth

Lil

tryptamine / 5-HT indazole analogs

tryptamine / 5-HT indazole analogs pharmacological data (rat uterus, rat blood pressure), synthesis of 1- and 2-sidechain analogs

#224

J. Am. Chem. Soc.

965

1958

C. Ainsworth

Lil

indazole-3-acetic acid

indazole-3-acetic acid from 2-NO₂-cinnamic acid (Fischer indazole synthesis), references

#223

J. Am. Chem. Soc.

967

1958

C. Ainsworth

Lil

4-alkylO- / 4-OH-3-Me-indazoles

4-alkylO- / 4-OH-3-Me-indazoles from 2,6-alkylO-/OH-acetophenone with 1. hydrazine, AcOH, 110°C 2. polyphosphoric acid, 115°C, yields 60% - 80% (4-OH: 34%), cool synthesis!

#205

J. Chem. Soc. Perk. I

1279

1993

Z. Zhenqi

Lil

2,6-dihydroxy-acetophenones

2,6-dihydroxy-acetophenone from 1,3-hydroxy-benzene and acetoacetate with 1. H₂SO₄ 2. Ac₂O 3. AlCl₃, 170°C 4. NaOH, H₂O, overall yield > 40%

#206

Org. Synth. Coll. Vol.

281

1955

A. Russell

Lil

subst. dimethylamino-propiophenone

2,4-dimethoxy-dimethylamino-propiophenone from 2,4-dimethoxy-acetophenone with dimethylamine-HCl, paraformaldehyde, and HCl in EtOH (Mannich reaction)

#207

J. Chem. Soc. Perk. I

471

1981

R. H. Carter

Lil

subst. dialkylamino-propiophenones

2-OH-(5-Me-)-dialkylamino-propiophenone from 2-OH-(5-Me-)acetophenone with dialkylamine, formaldehyde 30%, and HCl gas in EtOH (Mannich reaction), yield ~60%

#208

Synth.

830

1988

S. J. Joglekar

Lil

subst. dialkylamino-propiophenones

2,4-dimethoxy-(6-MeO-)-dialkylamino-propiophenone from 2,4-dimethoxy-(6-MeO-)acetophenone with dialkylamine, formaldehyde, and HCl in EtOH (Mannich reaction) (patent: Fr 1,492,256)

#209

35958v

1968

S.O.R.I.

Lil

subst. dimethylamino-propiophenones

subst. dimethylamino-propiophenones from acetophenone with dimethylamine-HCl, formaldehyde, and HCl in EtOH (Mannich reaction)

#210

Eur. J. Med. Chem.

545

1987

J. R. Dimmock

Lil

subst. dimethylamino-propiophenones

2,4-dihydroxy-dimethylamino-propiophenones from 2,4-dihydroxy-acetophenone with dimethylamine-HCl, paraformaldehyde, and HCl in EtOH (Mannich reaction), yield ~9%

#211

Arch. Pharm.

299

552?

1966

?. Zymalkowski

Lil

subst. dimethylamino-propiophenone

pharmacology of subst. dimethylamino-propiophenones, synthesis: reference #210

#212

Pharmazie

538

1991

J. R. Dimmock

Lil

2,6-dihydroxy-alkanoylbenzenes

2,6-dihydroxy-alkanoylbenzenes from 2,6-dimethoxy-benzonitriles with 1. AlkylMgCl 2. AlCl₃, yield ~70%

#214

J. Am. Chem. Soc.

1313

1942

A. Russell

Lil

2,6-dimethoxy-acetophenone

2,6-dimethoxy-propiophenone from 1,3-dimethoxybenzene with 1. PhLi 2. acetylchloride, yield 14% (intermediate)

#215

Ann.

709

1967

K.-H. Boltze

Lil

2-MeO-dimethylamino-propiophenone

2-MeO-dimethylamino-propiophenone from 2-MeO-acetophenone with dimethylamine-HCl, paraformaldehyde, and HCl in EtOH (Mannich reaction), yield ~70%

#216

Tet.

4729

1967

G. L. Buchanan

Lil

2,6-dihydroxy-acetophenone

2,6-dihydroxy-acetophenone, synthesis like reference #206

#217

J. Org. Chem.

2881

1967

E. Marcus

Lil

piperazine-indazol analogs of tryptamine

phenylpiperazine-indazol analogs of tryptamine via 2-NO₂-cinnamic acid, 2-NH₂-cinnamic acid (H₂, Raney Ni, 45 psi), indazole-3-acetic acid (HCl, NaNO₂, Na₂SO₃), phenylpiperazinyl-ethyl-indazol (iso-BuO₂CCl, NEt₃, phenylpiperazine) (patent US 3,488,353)

#219

66979u

1970

S. Archer

Lil

piperazine-indazol analogs of tryptamine

phenylpiperazine-indazol analogs of tryptamine via 5-MeO-2-NO₂-benzaldehyde, 5-MeO-2-NO₂-cinnamic acid, 2-NH₂-cinnamic acid (conc. NH₃, FeSO₄), indazole-3-acetic acid (HCl, NaNO₂, Na₂SO₃), (patent Fr. 1,434,479)

#220

20150c-g

1966

A. Hofmann

Lil

indazole-3-aldehyde

indazole-3-aldehyde from indazole-3-COOH with hydrazine

#221

J. Chem. Soc.

5901

1963

G. R. Bedford

Lil

piperazine-indazol analog of tryptamine

phenylpiperazine-indazol analog of tryptamine (patent US 3,362,956)

#222

10467w

1968

S. Archer

Lil

2,6-dimethoxy-acetophenone

2,6-dimethoxy-propiophenone from 1,3-dimethoxybenzene with 1.BuLi 2. ethyl acetate, yield 60%

#225

J. Org. Chem.

3559

1974

R. Levine

Lil

2,6-dimethoxy-valerophenone

2,6-dimethoxy-iso-valerophenone from 2,6-dimethoxy-benzonitrile with iso-BuMgBr

#226

J. Chem. Soc.

1163

1933

A. Robertson

Lil

2,6-dihydroxy-alkanoylbenzenes

2,6-dihydroxy-alkanoylbenzenes, synthesis like reference #206

#227

J. Med. Chem.

1194

1977

A. Bobik

Lil

3-C-glycosyl-indazoles

3-C-glycosyl-indazoles from diazaketoses and anthranilic acids

#228

J. Het. Chem.

1241

1976

E. García-Abbad

Lil

3-alkyl-indazoles

3-alkyl-indazoles via 2-amino-benzonitroiles, 2-amino-alkanoylbenzens (alkylMgX), 3-alkyl-indazoles (Fischer indazole synthesis with SO₂ / H₂0)

#229

Pharmazie

534

1976

E. Hannig

Lil

3-Me-indazole

3-Met-indazole from 2-F-acetophenone or 2-NH₂-acetophenone

#230

J. Med. Chem.

2708?

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7-subst. tryptamines

7-Me-tryptamines

7-Me- / 5-Me- / 4-F-7-Me-tryptamine through Abramovitch / Shapiro route

#231

J. Am. Chem. Soc.

4699

1948

Z. Pelchowicz

Lil

7-Me-N,N-dimethyltryptamine

7-Me-N,N-dimethyltryptamine Speeter / Anthony synthesis, selective synaptosomal 5-HT uptake inhibitor, rat behavioural data, synaptosomal uptake data

#232

Res. Comm. Chem. Path. Pharmacol.

161

1978

R. A. Glennon

Lil

4-OH-7-Me-indole

4-OH-7-Me-indole via 2-NO₂-4-BzO-toluene, 2-NH₂-4-BzO-toluene (H₂, Raney Ni, yield 84%), N-(5-BzO-2-Me-phenyl)-aminoacetaldehyde acetal (NaNH₂, chloroacetaldehyde acetal, yield 70%), 4-BzO-7-Me-indole (aniline-HCl, heat, yield 6% (sic))

#233

Helv. Chim. Acta

1203

1968

F. Troxler

Lil

7-Me-tryptamines

7-Me-tryptamines from 2-Me-hydrazine and aminobutyraldehyde diethylacetal with ZnCl₂

#234

Monaths. Chem.

404

1950

K. Eiter

Lil

7-Me-5-MeO-N,N-dimethyltryptamine

7-Me-5-MeO-N,N-dimethyltryptamine from dimethylpyrone, Leimgruber / Batcho reaction, Speeter / Anthony reaction

#235

J. Het. Chem.

749

1976

F. Benington

Lil

7-Br-4-MeO-N,N-dimethyltryptamines

7-Br-4-MeO-N,N-dimethyltryptamine via 2-MeO-5-Br-benzaldehyde, 4-MeO-7-Br-indole (1. ethyl azidoacetate 2. heat, catalyst), Speeter / Anthony reaction

#236

J. Het. Chem.

1373

1981

S. Samreth

Lil

7-Br- and 5-MeO-DMT, 5-HT₂ binding

21 subst. tryptamines incl. 7-Br- and 5-MeO-DMT, 4 subst. PIA, rat 5-HT₂ (ketanserin, DOB) binding data

#244

Eur. J. Pharmacol.

145

291

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R. A. Lyon

Lil

1- and 7-alkyl subst. alpha-Me-tryptamines

9 DOM alpha, N-analogues, 7 tryptamines, isomers, rat drug discrimination data (DOM)

#258

Biochem. Pharmacol.

1267

1983

R. A. Glennon

Lil

8 subst. DMT

8 subst. DMT incl. 7-Me-, 7-Et-, 7-Br-, 5-MeO-7-Me-, 6-Me-, 5-MeO-6-Me-DMT, rat stomach fundus strip data, rat drug discrimination data, comparison to 5-MeO-DMT (all are weaker or different) and DMT (some are stronger)

#324

J. Med. Chem.

1222

1980

R. A. Glennon

Lil

12 tryptamines incl. 7-subst., 2 PEA

12 tryptamines incl. 7-subst., 2 PEA, rat drug discrimination, rat stomach fundus strip data

#325

Psychopharmacology

155

1980

R. A. Glennon

Lil

binding data

31 PEA, 5-HT_2A, _2C binding

31 ring substituted PEA and PIA, rat 5-HT_2A (ketanserin) and _2C (mesulergine) binding data

#243

J. Med. Chem.

734

1992

R. A. Glennon

Lil

21 tryptamines, 4 PIA, 5-HT₂ binding

21 1-, 4-, 5-, 6-, 7-, alpha-, and N-subst. tryptamines, 4-iso-tryptamine, and 4 subst. PIA, rat 5-HT₂ (ketanserin, DOB) binding data, low / high aff. binding data

#244

Eur. J. Pharmacol.

145

291

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R. A. Lyon

Lil

rat vs. hum. 5-HT₂ binding

13 different tryptamines and PIA, rat and hum. 5-HT₂ (ketanserin) binding data, autoradiography

#246

Psychopharmacol.

495

1989

B. Sadzot

Lil

17 PIA

17 PIA, rat 5-HT₂ (ketanserin) and 5-HT₁ (LSD) binding data, low / high aff. binding data

#247

Eur. J. Pharmacol.

102

1984

M. Shannon

Lil

N-Me-DOB derivatives

sec., tert., and quart. N-Me-DOB derivatives, rat. 5-HT₂ (ketanserin, DOB) binding data, rat drug discrimination data (DOB)

#248

J. Med. Chem.

930

1987

R. A. Glennon

Lil

5-MeO/OH-N,N-di-Pr/Me/H-tryptamines

5-MeO/OH-N,N-di-Pr/Me/H-tryptamines, rat 5-HT_1A (8-OH-DPAT), _1B (serotonin), ₂ (ketanserin, DOB) binding data, rat drug discrimination data (8-OH-DPAT, DOM)

#249

J. Med. Chem.

867

1988

R. A. Glennon

Lil

N-methyl-N-isopropyl-tryptamines

8 indole-subst. N-methyl-N-isopropyl-tryptamines, hum. activity data

#250

J. Med. Chem.

892

1985

D. B. Repke

Lil

(±)/(+)/(-)-5-MeO-alpha-Me-tryptamine

(±)/(+)/(-)-5-MeO-alpha-Me-tryptamine and 5-MeO-DMT, rat drug discrimination data (DOM)

#251

Biol. Psychiatry

493

1983

R. A. Glennon

Lil

13 DOB analogues

13 DOB analogues, rat 5-HT₁ (serotonin) and ₂ (ketanserin) binding data, rat drug discrimination data (DOM)

#252

J. Med. Chem.

194

1986

R. A. Glennon

Lil

5-HT_1A binding review

5-HT_1A binding review, many classes of compounds incl. subst. tryptamines and MTHPI

#253

Pharmacol. Biochem. Behav.

1041

1991

D. L. Nelson

Lil

4-(2-butyl)/(2-Me-propyl-2,5-DMA

4-(2-butyl)/(2-Me-propyl-2,5-DMA, rat drug dicrimination data (LSD)

#254

J. Med. Chem.

788

1984

R. A. Oberlender

Lil

10 PIA, DMT, 5-MeO-DMT, 7-Me-DMT

10 PIA, DMT, 5-MeO-DMT, 7-Me-DMT, rat stomach fundus strip data

#255

J. Med. Chem.

822

1978

R. A. Glennon

Lil

quipazines, naphtylpiperazines

quipazines, naphtylpiperazines, rat 5-HT₁ (serotonin) and ₂ (ketanserin) binding data, rat drug discrimination data (DOM, TFMPP)

#256

J. Med. Chem.

2375

1986

R. A. Glennon

Lil

1- and 7-alkyl subst. alpha-Me-tryptamines

1-Pr-/Am-/oct-/Bz- and 7-Pr-/Am-(alpha-Me)-tryptamines, rat 5-HT₁ (serotonin) and ₂ (ketanserin, DOB) binding data

#257

J. Med. Chem.

2777

1990

R. A. Glennon

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9 DOM analogues, 7 tryptamines

9 DOM alpha, N-analogues, 7 tryptamines, isomers, rat drug discrimination data (DOM)

#258

Biochem. Pharmacol.

1267

1983

R. A. Glennon

Lil

5-MeO-alpha-Me-tryptamine

5-MeO-alpha-Me-tryptamine, hum. activity data

#259

Biol. Psychiatry

349

1980

R. E. Kantor

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45 PEA and PIA

45 PEA and PIA, rat stomach fundus strip data

#260

J. Med. Chem.

294

1980

R. A. Glennon

Lil

4-, 5-, 6-(di)MeO- and MeS-DMT

4-, 5-, 6-(di)MeO- and MeS-DMT, rat stomach fundus strip data, photoelectron spectra

#261

J. Med. Chem.

1381

1982

T. B. Kline

Lil

tryptamine 1-C- and 2,3-dihydro analogues

tryptamine 1-C- and 2,3-dihydro analogues, phenylalkylamines, rat stomach fundus strip data

#262

J. Med. Chem.

1982

R. A. Glennon

Lil

4-/5- MeO-/MeS-DMT

4-/5- MeO-/MeS-DMT, rat drug discrimination data (5-MeO-DMT)

#263

Life Sci.

465

1982

R. A. Glennon

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tryptamines hum. activity review

tryptamines and beta-carbolines review, hum. activity data

#264

J. Psychoact. Drugs

347

1984

D. J. McKenna

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5-MeO-alpha-Me-tryptamine hum. activity

5-MeO-alpha-Me-tryptamine, hum. activity

#266

J. Psychoact. Drugs

247

1979

A. T. Shulgin

Lil

DOB hum. activity

DOB, hum. activity

#267

J. Psychoact. Drugs

1981

A. T. Shulgin

Lil

DOM hum. activity

DOM, hum. activity

#268

J. Psychoact. Drugs

171

1977

A. T. Shulgin

Lil

(2,6-di-Me-) N-piperidyl analogs of 5-HT

(2,6-di-Me-) N-piperidyl analogs of 5-HT, binding data for many 5-HT receptors, poor 5-HT₂ affinity

#269

Med. Chem. Res

254

1994

M. Dukat

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agonist vs. antagonist label

the effect 5-HT_2A agonist, partial agonist, and antagonist radiolabels on binding affinity

#270

Biochem. Pharmacol.

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A. J. Sleight

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49 subst. phenylalkylamines

49 phenylaklylamines, rabbit hyperthermia data, cat EEG data, rat open field data

#271

J. Med. Chem.

1100

1974

F. A. B. Aldous

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13 4-subst PIA

13 4-subst PIA, rat stomach fundus strip data, rat drug discrimination data (DOM)

#272

J. Med. Chem.

1163

1982

R. A. Glennon

Lil

PEA-ergoline hybride

PEA-ergoline hybride molecule as muscarinic antagonist, rat 5-HT_1A (5-OH-DPAT) and 2A (ketanserin), cloned hum. 5-HT_2A (ketanserin), _2B (rauwolscine), _2C (mesulergine), and cloned muscarinic receptor binding data, rat drug discrimination data (LSD)

#273

J. Med. Chem.

2134

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A. P. Monte

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1-iso-N,N-dimethyl-tryptamines

(6-MeO-/5-MeO-) 1-iso-N,N-dimethyl-tryptamines, rat 5-HT (serotonin) binding data, rat drug discrimination data (DOM, 6-MeO-iso-DMT has 1/3 the activity of 5-MeO-DMT), rat stomach fundus strip data

#275

J. Med. Chem.

1984

R. A. Glennon

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subst. alpha-Me-tryptamine enantiomers

subst. alpha-Me-tryptamine enantiomers, rat 5-HT₁ (serotonin) and ₂ (ketanserin) binding data

#276

J. Med. Chem.

1406

1988

D. E. Nichols

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amphetamine potentiation by 5-HT_2A/_2C agonists

5-HT_2A/_2C agonists potentiate amphetamine stimulus cue, rat drug discrimination data (amphetamine)

#277

Neuropharmacology

1471

1997

D. Marona-Lewicka

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subst. N,N-dialkyltryptamines, CAR

4-OH-, 5-OH-/AcO-, 4-/5-/6-/7-MeO-DMT, (5-MeO-) DET, rat conditioned avoidance response test data, partition coeff. (psilocin is very lipophilic)

#278

Life Sci.

267

1968

P. K. Gessner

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5-HT analogues, uterus and fundus data

24 5-HT analogues (N-subst, o-Bz), rat uterus and rat stomach fundus strip data, many of them are antagonists

#279

Brit. J. Pharmacol.

265

1959

R. B. Barlow

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5-HT receptor ligands review

review of 5-HT receptor ligands, 2-naphtyl-isopropylamine

#280

J. Med. Chem.

1987

R. A. Glennon

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5-HT receptor ligands review

review of 5-HT receptor ligands, 1-naphtyl-isopropylamine

#281

Serotonin Receptor Subtypes: Basic and Clinical Aspects. Wiley-Liss, Inc.

1991

R. A. Glennon

Lil

MDL-aryloxyalkylimidazolines, 5-HT_2A and _2C

3 aryloxyalkylimidazolines and some agonists and antagonists, cloned rat 5-HT_2A and _2C (I-LSD, 5-HT) receptor binding and efficiency data, 2 are weak agonists, 1 is a weak antagonist

#282

Eur. J. Pharmacol.

296

307

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B. W. Siegel

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5-HT₂ agonists and antagonists, 5-HT_2A and _2C

5-HT₂ agonists and antagonists, cloned hum. 5-HT_2A (ketanserin) and _2C (mesulergine) receptor binding and efficiency data

#283

J. Neurochem.

2521

1996

R. A. Newton

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N-subst. (4-OH-, 5-oR-, 5-Me-, 6-MeO-) tryptamines

21 N-subst. (4-OH-, 5-oR-, 5-Me-, 6-MeO-) tryptamines incl. N-cycl. analogues, rat 5-HT_2A (DOI, ketanserin) and _1A (8-OH-DPAT) binding data, 4-OH-tryptamines are selective for 5-HT_2A vs. _1A

#284

Neuropharmacol.

193

1990

D. J. McKenna

Lil

4-(2-butyl)-DMA isomers, 5-HT_2A

4-(2-butyl)-DMA isomers, rat 5-HT_2A (DOI) binding data, rat drug discrimination data, no big difference between isomers

#285

J. Med. Chem.

3593

1995

R. Oberlender

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4-subst. DMA

27 4-subst DMA, rat 5-HT₂ (ketanserin) binding data, rat thoracic aorta contraction data, longer hydrophobic substituted DMA are antagonists

#286

J. Med. Chem.

1032

1990

M. R. Seggel

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27 subst. tryptamines, fundus data

27 subst. tryptamines, rat stomach fundus strip data

#288

J. Med. Chem.

427?

1979

R. A. Glennon

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tetraline / indan DOM analogs

tetraline / indan DOM analogs, rat CAR data, sheep umbilical artery data, rat stomach fundus strip data, no / only weak DOM like activity

#323

J. Med. Chem.

161

1974

D. E. Nichols

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12 tryptamines incl. 7-subst., 2 PEA

12 tryptamines incl. 7-subst., 2 PEA, rat drug discrimination, rat stomach fundus strip data

#325

Psychopharmacology

155

1980

R. A. Glennon

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phenyl-, benzoyl-piperazine amphetamine analogs

#327

J. Med. Chem.

630

1986

R. A. Lyon

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phenyl-cyclobutylamine analogs of PIA

phenyl-cyclobutylamine analogs of PIA, drug discrimination (LSD) data

#328

J. Med. Chem.

1108

1984

D. E. Nichols

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5-OH-DMT esters

5-OH-DMT esters, rat stomach fundus strip data, partition coeff. data, all have higher affinity than 5-MeO-DMT, 5-acetoxy-DMT has higher affinity than 5-OH-DMT

#329

J. Med. Chem.

1414

1979

R. A. Glennon

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alpha-Me-5-HT, 2-Me-5-HT, 2-Me-5-MeO-T

alpha-Me-5-HT, 2-Me-5-HT, 2-Me-5-MeO-T, rat 5-HT_1A (8-OH-DPAT), _1B (5-HT), _2C (5-HT), bovine 5-HT_1D (5-HT), human 5-HT_1E (5-HT), rat 5-HT₂ (ketanserin) receptor binding data

#330

J. Med. Chem.

755

1990

A. M. Ismaiel

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17 agonists and 12 antagonists binding data

17 agonists incl. 14 tryptamines and LSD, and 12 antagonists, pig 5-HT_1A (8-OH-DPAT), _1B (I-CYP), _2C (mesulergine), rat 5-HT₂ (ketanserin) receptor binding data

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Arch. Pharmacol.

332

1986

G. Engel

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5-HT_2C agonists, 1-isotryptamines

5-F-6-Cl-indole synth, 5-HT_2C agonists incl. subst. alpha-Me-1-isotryptamines and 5-F-alpha-MT, hum. 5-HT_2A (DOB) and _2C (5-HT) receptor binding data, IP accumulation data, rat polydipsia model data, rat penile erection data

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J. Med. Chem.

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M. Bös

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5-HT_2C agonists Ro 60-0175 and Ro 60-0332

5-HT_2C agonists 5-Fl-6-Cl-alpha-Me-1-isotryptamine (Ro 60-0175) and Ro 60-0332, pharmacological data

#333

J. Pharm. Exp. Ther.

286

913

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J. R. Martin

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5,N-subst. alpha-4 methylene bridged tryptamines

5, N-subst. alpha/4 methylene bridged tryptamines, rat 5-HT₁ (5-HT) and 5-HT₂ (spiperone) binding data, some have good 5-HT₂ binding affinities (antagonist labeled!)

#334

J. Med. Chem.

1746

1988

M. E. Flaugh

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5-acetyl-N,N-dipropyl alpha-4 methylene bridged T

5-acetyl-N,N-dipropyl alpha-4 methylene bridged tryptamine LY293284, extensive binding data, pharmacological data, specific for 5-HT_1A

#334

J. Med. Chem.

1746

1988

M. M. Foreman

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SK&F 103829 5-HT₂ agonist

SK&F 103829, a weak 5-HT₂ partial agonist, pharmacological data

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Br. J. Pharmacol.

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264

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E. M. Taylor

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26 5-HT₂ ligands binding data

review of 5-HT_2C receptor pharmacology, 5-HT_2C and 2A receptor binding data for 26 ligands

#337

TIPS

1988

D. Hoyer

Lil

tiflucarbine

antidepressant tiflucarbine, rat drug discrimination (8-OH-DPAT, DOM, 5-MeO-DMT) data, 5-HT receptor binding review, effects probably not 5-HT_2A or _1A receptor mediated

#338

Pharmacol. Biochem. Behav.

769

1990

R. A. Glennon

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TFMPP and restricted (2-2' ethylen-bridged) TFMPP

TFMPP and restricted (2-2' ethylen-bridged) TFMPP analog, 5-HT₁ and 5-HT₂ binding data

#339

J. Med. Chem.

945

1985

J. R. Huff

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5-HT receptor ligands review

#340

Pharmacol. Biochem. Behav.

1009

1991

R. A. Glennon

Lil

LSD, DMT, DOI, and DOB binding data

LSD, DMT, DOI, and DOB, hum. 5-HT_1A (8-OH-DPAT), _1D (5-HT), 5-HT_2A (ketanserin, DOB), alpha1-adrenergic, alpha2-adrenergic, beta-adrenergic, muscarinic, and benzodiazepine receptor binding data

#341

Psychopharmacology

118

1989

P. A. Pierce

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(6-MeO-) THBC

(6-MeO-) THBC, rat drug discrimination (LSD) data, rat receptor (LSD) binding data, (6-MeO-) THBC have weak LSD-type effects

#342

Life Sci.

2433

1982

E. B. Nielsen

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DMT as at 5-HT_2A agonist

DMT binding and IP accumulation with hum. 5-HT_2A and C receptor cell lines, rat drug discrimination tests with agonists and antagonists

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Pharmacol. Biochem. Behav.

323

1998

R. L. Smith

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DOB, DOM, MDA, and antagonists 5-HT_2C activity

DOB, DOM, MDA, and antagonists 5-HT_2C activity, rat choroid plexus celles IP accumulation data

#383

Psychopharmacology

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340

1991

E. Sanders-Bush

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17 DMA derivatives

14 4-subst DMA derivatives, 3 N-subst DOB derivatives, cloned hum 5-HT_2A, _2B, _2C, cloned rat 5-HT_2B ([ ³ H]5-HT, [ ¹²⁵ I]DOI) receptor binding data

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Arch. Pharmacol.

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D. L. Nelson

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MAO

subst amphetamines as MAO-A inhibitors

31 subst. amphetamines incl. amphetamine, MTA, ETA, DOB, DOM, MDMA as reversible MAO-A specific inhibitors, MTA and ETA have the highest activity and MTA has a more than 1000 fold selectivity over MAO-B

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Biochem. Pharmacol.

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M. C. Scorza

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1-Me-betaC and betaC binding sites

1-Me-betaC and betaC binding sites in rat brain and liver

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Arch. Pharmacol.

349

308

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T. May

Lil

22 MAOIs, MAO-A and MAO-B inhibition data

22 substances (incl. 1-Me-betaCs, tryptamines, reversibel and irreversibel MAOIs), MAO-A and MAO-B inhibition data, 1-Me-betaC binding to rat brain MAO, 1-Me-betaCs and 5-F-alphaMT are specific MAO-A inhibitors

#291

J. Neurochem.

490

1991

T. May

Lil

tryptamines and betaCs MAOI

tryptamines and betaC in plant samples, self experiments, subst. tryptamines GC data, THbetaCs MS data, MAO inhibition data for 10 subst. tryptamines incl. psilocine, short review of subst. tryptamines and betaCs MAO inhibition

#292

J. Ethnopharmocol.

179

1984

D. J. McKenna

Lil

myristicin and nutmeg as MAO inhibitors

myristicin and nutmeg as putative weak MAO inhibitors

#293

647

1963?

E. B. Truitt

Lil

tyramine pressor effect under moclobemide

human tyramine pressor effect under moclobemide (reversible MAO-A-I), effect of tyramine added to different meals

#294

J. Clin. Pharmacol.

507

1992

C. Audebert

Lil

tyramine in foods

tyramine content of hundreds of foods, tyramine pressor effect review, reversible vs. irreversible MAOI, mild cheeses, beer, wine, meat products in normal amounts are ok, heavily fermented cheese and meat products only in small amounts, MAOI after meal

#295

J. Neural Transm. (Suppl.)

1988

M. Da Prada

Lil

tyramine effect, reversible vs. irreversible MAOI

human tyramine pressor effect under various reversible and irreversible MAOI, tyramine-cheese has lower effects than pure tyramine

#296

J. Neural Transm. (Suppl.)

1988

P. R. Bieck

Lil

human tyramine effect under moclobemide

human tyramine pressor effect under moclobemide (reversible MAO-A-I) or tranylcypromine, effect of tyramine added to meal

#297

J. Neural Transm. (Suppl.)

1988

A. Korn

Lil

short comment on MAO-A-I

short comment on MAO-A-I and the tyramine effect, no references

#298

J. Neural Transm. (Suppl.)

123

1988

O. J. Rafaelsen

Lil

human tyramine pressor effect under moclobemide

human tyramine pressor effect under moclobemide (reversible MAO-A-I), tyramine added to meal

#299

J. Neural Transm. (Suppl.)

1988

R. Gieschke

Lil

human tyramine pressor effect under moclobemide

human tyramine pressor effect under moclobemide (reversible MAO-A-I), tyramine added to meal, effect of MAOI ingestion before / with meal

#300

J. Neural Transm. (Suppl.)

105

1988

T. Müller

Lil

in vitro tests of MAOI - tyramine effects, review

#301

J. Neural Transm. (Suppl.)

1988

B. A. Callingham

Lil

review of reversible vs. irreversible MAO-A-I

review of reversible vs. irreversible MAO-A specific inhibitors, tyramine pressor effect, toxicity

#302

J. Neural Transm. (Suppl.)

1988

M. Da Prada

Lil

rat tyramine pressor effect under MAOI

rat tyramine pressor effect under 4 reversible MAO-A-I or 1 irreversible MAOI

#303

J. Neural Transm. (Suppl.)

1988

J. P. M. Finberg

Lil

alpha-MT, alpha-Me-Trp, MAO inhibition

(5-OH-) alpha-MT and -ET from indolecarbaldehydes, (5-OH)alpha-alkyl-Trp from gramines and nitropropionates, MAO and 5-OH-Trp decarboxylase inhibition data

#30

J. Org. Chem.

1548

1960

R. V. Heinzelmann

Lil

tryptamines from indole (-aldehyde)

5-OH-tryptamines, alpha-MT, 5-BzO-indole

5-OH-tryptamines and alpha-MT from indole via 3-formyl-indole, nitroalkenylindole, 5-BzO-indole from p-BzO-aniline via phenylhydrazone and 5-BzO-indole-2-carboxylate, yield 60%

#306

J. Chem. Soc.

3887

1958

A. S. F. Ash

Lil

indole-3-Zn reactions

many (1- or 2-substituted) indoles, indole-3-acetic acids from indoles with n-BuLi and ZnCl₂

#307

J. Med. Chem.

5119

1996

R. D. Dillard

Lil

indole 3-alkylation by alcohols

indole 3-alkylations by alcohols in refluxing p-cymene (183°C) with NaOH, nickel catalyst, and water removal

#308

J. Am. Chem. Soc.

5248

1957

E. F. Pratt

Lil

(5-OH-)(alpha-alkyl-)tryptamines

(5-OH-)(alpha-alkyl-)tryptamines from indoles via 3-formyl-indoles with Vilsmeier formylation, 3-nitroalkenyl-indoles with nitroalkan and ammonium acetate at reflux, first paper for this route

#317

J. Chem. Soc.

3493

1958

E. H. P. Young

Lil

5-EtO-T

5-EtO-T from 2-NO₂-5-OH-toluene via 2-NO₂-5-EtO-toluene, 2-NO₂-phenylpyruvate, 2-hydrazo-phenylpyruvate, 2-COOEt-indole (very poor yield), 2-COOH-indole, indole, indolyl-MgBr, indolylacetonitril with Cl-acetonitril, method ref. #110 + Ann. 513, 1 1934

#318

Ann.

516

1935

T. Hoshino

Lil

5-F-indole, 5-F-DMT, 5-F-DET

5-F-DMT and 5-F-DET from 3-F-toluene, 3-F-benzaldehyde, 3-F-6-NO₂-benzaldehyde, 3-F-6-NO₂-nitrostyrene, 5-F-indole, yield 29% over all, Speeter / Anthony route

#319

J. Chem. Soc.

5418

1961

Z. Pelchowicz

Lil

4-, 5-, 6-, and 7-isotryptamines

4-, 5-, 6-, and 7-isotryptamines from formylindoles

#305

Helv. Chim. Acta

1616

1968

F. Troxler

Lil

alpha-MT, alpha-Me-Trp

(5-OH)alpha-MT and -ET from indolecarbaldehydes, (5-OH)alpha-alkyl-Trp from gramines and nitropropionates, MAO and 5-OH-Trp decarboxylase inhibition data

#30

J. Org. Chem.

1548

1960

R. V. Heinzelmann

Lil

subst. tryptamines

many, many tryptamines through Abramovich, indolylacetone reductive amination, indolylmagnesiumbromide, indolylcarbaldehyde and gramine with nitroalkanes, tryptamine acylation / LiAlH₄ reduction...

#43

J. Chem. Soc.

7165

1965

B. Heath-Brown

Lil

indole-3-acylation and reduction with NaBH₄ / TFA

1-phenylsulfonyl-indole 3-acylation with RCOCl / AlCl₃, yields > 81%, reduction to 1-phenylsulfonyl-3-alkyl-indoles with NaBH₄ / TFA yields > 96%

#546

J. Org. Chem.

5451

1985

D. M. Ketcha

Lil

designer drugs

designer drugs review

designer drugs: amphetamine analogs review, mescaline SPECT study

#345

Pharm. i. u. Zeit

1990

K. A. Kovar

Lil

designer drugs review

designer drugs: amphetamine analogs analytics, DC, Rf of 16 substances in 4 solvent systems, colour reactions, UV, IR, and ¹ H- and ¹³ C-NMR spectra, DC-IR

#346

Pharm. i. u. Zeit

211

1990

K. A. Kovar

Lil

structure and activity of hallucinogens review

#347

Chem. i. u. Zeit

147

1979

W. Hänsel

Lil

designer drug review

designer drug review: amphetamine, PCP, fentanyl, and prodine analogs, list of suspected chemicals

#349

Dtsch. Apoth. Zeitg.

127

1569

1987

K. A. Kovar

Lil

futute synthetic drugs of abuse

future synthetic drugs of abuse, many compound classes, many references

#350

available from WWW

D. A. Cooper

Lil

short review

short review on hallucinogens, entactogens and phencyclidins

#465

???

Lil

reviews

hallucinations review

hallucinations classification and reporting methods review, no refs.

#344

Scient. Am. ?

132

1974?

R. K. Siegel

Lil

good old review of psychotomimetics chemistry

good old review of psychotomimetic chemistry

#348

Medicinal Chemistry, Ed. G. deStevens, Psychopharmacological Agents Vol. 1, Ed. M. Gordon, Academic Press, NY

4-1

555

1964

D. F. Downing

Lil

indole review

indole chemistry review

#574

Indoles, Best Synthetic Methods Series, Academic Press, San Diego, CA

1996

R. J. Sundberg

Lil

lysergamides

1-Me-lysergic acid butanolamide potentiates DMT effects

1-Me-lysergic acid butanolamide (UML-491) potentiates DMT effects in human

#351

Experientia

137

1962

A. Sai-Halász

Lil

ergot alkaloids review

extensive review on ergot alkaloids

#352

Die Mutterkornalkaloide, Sammlung Chem. Techn. Beitr., Ferdinand Enke Verlag, Stuttgart

1964

A. Hofmann

Lil

ergoline derivatives review

review on ergolin derivatives as pharmaceuticals

#353

Pharmaz. Zeitg.

137

1992

E. Eich

Lil

lysergamides from mixed anhydride activation

lysergamides from mixed anhydride activation, LiOH / SO₃ method

#354

J. Org. Chem.

368

1959

W. L. Garbrecht

Lil

N-alkyl-nor-LSD derivatives

N(6)-alkyl-nor-LSD derivativesrat drug discrimination data

#355

J. Med. Chem.

1252

1985

A. J. Hoffman

Lil

mono-(2-alkyl)-lysergamides

mono-(2-alkyl)-lysergamides via POCl₃ method, rat 5-HT_1A (8-OH-DPAT) and 2A (ketanserin) binding data, rat drug discrimination (LSD) data, crystal structures, some have LSD-like activity, all have higher 5-HT_1A affinities

#356

J. Med. Chem.

958

1995

A. P. Monte

Lil

slow dissociation of LSD and BOL from 5-HT_2A receptor

slow dissociation of LSD and BOL from 5-HT_2A receptor, cloned rat membrane 5-HT_2A binding data, t_1/2 = 20 min, PI accumulation data

#357

Mol. Pharmacol.

826

1992

K. D. Burris

Lil

alkyl--isopropyl-lysergamides

alkyl-isopropyl-lysergamides, rat 5-HT_1A (8-OH-DPAT) and 2A (ketanserin) binding data, rat drug discrimination (LSD) data, crystal structures,all have LSD-like activity, all have higher 5-HT_1A affinities

#358

J. Med. Chem.

958

1995

A. P. Monte

Lil

LSD as 5-HT_2C receptor agonist

LSD, but not BOL and lisuride, as 5-HT_2C receptor agonist, rat IP accumulation data

#359

J. Pharm. Exp. Ther.

258

891

1991

K. D. Burris

Lil

LSD-like effects of methylergonovine in human

LSD-like effects of methylergonovine and related compounds in human

#360

J. Psyched. Drugs

165

1980

J. Ott

Lil

LSD, psilocybin, and TMA-2 crystal structures

LSD, psilocybin, and TMA-2 X-ray crystal structures

#361

Mol. Pharmacol.

1973

R. W. Baker

Lil

lysergic acid total synthesis

lysergic acid 15 step total synthesis

#362

J. Am. Chem. Soc.

3087

1978

E. C. Kornefeld

Lil

lysergic acid total synthesis

#365

J. Am. Chem. Soc.

5256

1954

E. C. Kornefeld

Lil

effects of LSD analogs in human

physical and psychic effects of LSD analogs in human

#368

Psychopharmacologia

1959

H. Isbell

Lil

LSD and psilocybin in human

physical and psychic effects of LSD and psilocybin in human

#369

Psychopharmacologia

1959

H. Isbell

Lil

LSD antagonism on 5-HT₂ IP accumulation

LSD antagonism on serotonin induced rat cortex 5-HT₂ IP accumulation

#370

J. Pharm. Exp. Ther.

247

918

1988

P. A. Pierce

Lil

dopamine D₁ binding data of LSD analogs

LSD N₆- and amide-analogs, rat dopamine D₁ binding data (SCH₂3390), AC activity test data

#371

Psychopharmacology

118

401

1995

V. J. Watts

Lil

methyl-propinyl-lysergamide

methyl-propinyl-lysergamide (LEK 8842) and analogs, 5-HT₂ and alpha-adrenoceptors isolated rat aorta contraction data

#372

Pharmacology

195

1992

I. Krisch

Lil

13- and 14-tBu lysergamides

13- and 14-tBu lysergamides and -reverse amides, rat alpha1, alpha2, D1, D2, 5-HT_1A and 5-HT₂ binding data, 14-t-butylation enhances affinities by 10 - 200 times

#373

Bioorg. Med. Chem. Lett.

1117

1998

S. Mantegani

Lil

LSD metabolism

[ ¹⁴ C]LSD metabolism in rat liver, 12-OR-LSD data

[ ¹⁴ C]LSD metabolism in perfused rat liver, synthesis, MS data, Rf values, and colour reactions (incl. 5-, 6-, 7-OH-indole) of metabolites incl. 12-OH-LSD

#363

Biochem. Pharmacol.

3081

1979

Z. H. Siddik

Lil

[ ¹⁴ C]LSD metabolism in rat, guinea pig, and monkey

[ ¹⁴ C]LSD metabolism in rat, guinea pig, and rhesus monkey, strong species differences

#364

Biochem. Pharmacol.

3093

1979

Z. H. Siddik

Lil

[ ¹⁴ C]LSD distribution in mouse

[ ¹⁴ C]LSD distribution and fate in mouse

#366

Experientia

396

1955

A. Stoll

Lil

[ ¹⁴ C]LSD distribution in mouse

[ ¹⁴ C]LSD distribution in mouse after intracerebral and intravenous injection

#367

Experientia

199

1957

T. J. Haley

Lil

12-OH-lysergamide from lysergamide

12-OH-lysergic acid butanolamide from lysergamide via Zn / HCl reduction to 2,3-dihydro-lysergamide and oxidation with potassium nitroso disulphonate NO(SO₃K)₂

#374

Helv. Chem. Acta

756

1964

P. A. Stadler

Lil

simplified LSD analogs

depyrrolo-LSD

depyrrolo-LSD synthesis, patent Fr 1,555,553, paper see #0375

#375

100543j

1970

M. Julia

Lil

depyrrolo-LSD

depyrrolo-LSD synthesis

#376

Bull. Soc. Chim.

4463

1968

M. Julia

Lil

depyrrolo-de-C₄-LSD

depyrrolo-de-C₄-LSD synthesis, highly active in reversing ileal contraction through ergonovine

#377

J. Org. Chem.

1669

1974

J. C. Craig

Lil

depyrrolo-methyl lysergate via photocyclization

#378

J. Chem. Soc. Perk I

2911

1984

I. Ninomiya

Lil

depyrrolo-LSD

depyrrolo-LSD 5-step synthesis, depyrrolo-ethyl lysergate is a potent oxytocics

#379

Chem. Pharm. Bull.

1641

1967

Z. Horii

Lil

depyrrolo-ethyl lysergate

depyrrolo-ethyl lysergate 4-step synthesis

#380

Chem. Pharm. Bull.

1641

1967

Z. Horii

Lil

chemistry of (depyrrolo-) lysergic acid derivatives

isomerizations of (depyrrolo-) lysergic acid derivatives, depyrrolo synthesis ref: T. Kiguchi Het. 19, 873 1982, Het. 18, 217 1982, Het. 22, 43 1984

#381

Het.

1719

1984

T. Kiguchi

Lil

5-NonO-tryptamines

NonO-tryptamine

NonO-tryptamine, serotonin, and sumatriptan, 5-HT_1A, _1B, _1Dalpha, _1Dbeta, _2A, _2C, and ₃ receptor binding data, AC activity data

#384

J. Med. Chem.

2828

1994

R. A. Glennon

Lil

alkylO-tryptamine

37 subst. 5-alkyl-O- and 5-alkanoyl-O-tryptamines and cyclic analogs, human 5-HT_1A, _1Dalpha, and _1Dbeta receptor binding data, NonO-DMT from tryptamine with NaCNBH₄, formaline, and acetic acid, yield 25%

#385

J. Med. Chem.

314

1996

R. A. Glennon

Lil

p-alkylO-anilines

p-alkylO-anilines from p-OH-formanilide via p-alkoxyformanilide with alkyl bromide, and alkaline hydrolysis

#386

J. Chem. Soc.

1573

1955

Ph. Buu-Hoï

Lil

p-alkylO-anilines

p-alkylO-anilines from p-OH-acetanilide via p-alkoxyacetanilide with alkyl bromide, and alkaline hydrolysis

#387

J. Med. Chem.

347

1984

C. D. Selassie

Lil

p-pentyl-O-phenylhydrazine

p-pentyl-O-phenylhydrazine from p-pentyl-O-aniline with 1. NaNO₂ / HCl 2. SnCl₂ / HCl

#388

J. Med. Chem.

307

1972

E. M. Kosower

Lil

p-alkylO-anilines

p-alkylO-anilines from p-OH-trifluoroacetanilide via p-alkoxy-trifluoroacetanilide with alkyl bromide, and gentle alkaline hydrolysis

#389

Coll. Czech. Chem. Commun.

595

1972

M. Machková

Lil

MDMA

2- / 5- / 6-Me-MDA

2- / 5- / 6-Me-MDA, rat drug discrimination data ((+)-amphetamine, (+)-MBDB, MMAI, LSD, DOI), rat synaptosomes monoamine uptake inhibition data (5-HT, DA, NE), they are potent and specific 5-HT uptake inhibitors and generalize to MBDB and MMAI

#409

J. Med. Chem.

1001

1998

M. A. Parker

Lil

MDMA and LSD synergism

strong synergism between MDMA and LSD in rat drug discrimination (MDMA) test

#410

Eur. J. Pharmacol.

341

131

1998

M. D. Schechter

Lil

beta-oxo-MDA / -MDMA, N-subst. cathinones

beta-oxo-MDA and -MDMA, rat drug discrimination data ((+)-amphetamine, DOM, MDMA), N-subst cathinone = beta-oxo-amphetamine rat drug discrimination data ((+)-amphetamine)

#411

Pharmacol. Biochem. Behav.

1109

1997

T. A. Dal Cason

Lil

subst. amphetamines review

hallucinogenic and serotonin releasing subst. amphetamines medicinal chemistry and structure-activity relationships review

#412

Amphetamine and its Analogs: Pharmacology, Toxicology, and Abuse, Ed. A. K. Cho, Academic Press, San Diego, CA

1994

D. E. Nichols

Lil

MDA and DOM indane and tetraline analogs

MDA 1-beta, 6-beta, and DOM 6-beta methylene and ethylene bridged indane and tetraline analogs, rat drug discrimination data (LSD, MDMA), rat monoamine (-metabolites) and paroxetine B_max long term effects, 1-beta-methylene-MDA generalizes + non-neurotoxic

#413

J. Med. Chem.

703

1990

D. E. Nichols

Lil

MTA

MTA, rat drug discrimination data (MDMA, (S)-MBDB, MMAI), rat monoamine (-metabolites) long term effects, rat synaptosomes 5-HT-, dopamine-, and NE-uptake inhibition data, rat cortex slice 5-HT-releasing data, MTA generalizes and is non-neurotoxic

#414

Eur. J. Pharmacol.

229

1992

X. Huang

Lil

hormone effects of MBDB, MMAI, and MTA

MBDB, MMAI, MTA effects on secretion of the hormones ACTH, corticosteron, prolactin, oxytocin, and renin

#415

J. Pharm. Exp. Ther.

279

1261

1996

Q. Li

Lil

MDA-methylendioxy analogs

MDA TH-benzofuran, indan, and tetralin methylendioxy-analogs, rat drug discrimination data (MMAI, (S)-MBDB, (S)-amphetamine), rat synaptosomes 5-HT-, dopamine-, and NE-uptake inhibition data

#416

J. Med. Chem.

3700

1993

A. P. Monte

Lil

MDMA neurotoxicity and free radicals

MDMA neurotoxicity through free radicals, rat monoamine (-metabolites) long term effects, microdialysis salicylic acid scavenging

#417

Br. J. Pharmacol.

121

889

1997

M. I. Colado

Lil

MDMA neurotoxicity, ascorbate and cysteine

MDMA neurotoxicity, ascorbate and cysteine before and after MDMA, rat 5-HT long term effects, ascorbate and cysteine prevent 5-HT long term effects

#418

J. Neural Transm.

103

1397

1996

G. A. Gudelsky

Lil

3-MeO-4-Me-amphetamine, MMAI, 5,6-methylendioxy-2-aminoindane

3-MeO-4-Me-amphetamine, MMAI, 5,6-methylendioxy-2-aminoindane, rat drug discrimination data (MDMA, (S)-MBDB, LSD, (S)-amphetamine), rat monoamine (-metabolites) and B_max long term effects, rat synaptosomes 5-HT uptake inhibition data

#419

J. Med. Chem.

1662

1991

M. P. Johnson

Lil

MMAI mechanism

MMAI mechanism of action, rat drug discrimination data (MMAI, MMAI + antagonists or uptake inhibitors, MMAI after p-Cl-Phe), rat adrenoceptor binding data, rat behavioural effects after MMAI and MMAI after p-Cl-Phe

#420

Eur. J. Pharmacol.

258

1994

D. Marona-Lewicka

Lil

5-IAI

5-I-2-aminoindan, rat drug discrimination data (MDMA, (S)-MBDB), rat monoamine (-metabolites) long term effects, rat synaptomes 5-HT uptake inhibition data

#421

Pharmacol. Biochem. Behav.

135

1991

D. E. Nichols

Lil

alpha-ethyl PCA analog = CAB

CAB = alpha-ethyl PCA analog, rat drug discrimination data (MDMA, (S)-MBDB), rat monoamine (-metabolites) acute and long term effects, rat long term paroxetine binding data, rat synaptosomes 5-HT- and dopamine-uptake inhibition data

#423

Eur. J. Pharmacol.

191

1990

M. P. Johnson

Lil

alpha-ethyl-tryptamine, AMT, alpha-ethyl DOM analog

alpha-ethyl-tryptamine, AMT, alpha-ethyl DOM analog, rat drug discrimination data (MDMA, amphetamine)

#425

Pharmacol. Biochem. Behav.

459

1993

R. E. Glennon

Lil

hyponatraemia after MDMA

hyponatraemia after MDMA and VP oversecretion

#426

Lancet

347

1052

1996

R. Holden

Lil

MDMA THIQ, indane, and tetraline analogs

(N-Me-) 5,6-/4,5-methylendioxy-2-aminoindan, -THIQ, 6,7-methylendioxy-2-aminotetralin, mouse locomotor activity and rearing, hum. 5-HT_2A (ketanserin, DOB) binding data, rat drug discrimination data (MDMA)

#428

Med. Chem. Res.

412

1996

L. Malmusi

Lil

(+)-MDA vs. (-)-MDA

rat drug discrimination data ((+)-MDA vs. (-)-MDA vs. saline)

#430

J. Pharm. Exp. Ther.

276

594

1996

R. Young

Lil

MDMA long term neurotoxicity

MDMA neurotoxicity over 52 weeks, rat monoamine (-metabolites) long term effects

#431

J. Pharm. Exp. Ther.

276

846

1996

K. E. Sabol

Lil

MDMA long term neurotoxicity

MDMA neurotoxicity over 52 weeks, rat 5-HT- and dopamine uptake binding site autoradiography data

#432

J. Pharm. Exp. Ther.

276

855

1996

R. Lew

Lil

MDMA toxicity review

#433

Psychopharmacol.

119

247

1995

A. R. Green

Lil

MDMA metabolites acute effects

MDMA metabolites, different metabolizing rats acute 5-HT depletion effect

#434

Biochem. Pharmacol.

789

1996

T. Chu

Lil

alpha-ethyl-tryptamine

alpha-ethyl-tryptamine, rat behavioural changes, fluoxetine pretreatment

#435

Psychopharmacol.

113

284

1993

K. M. Krebs

Lil

PCA neurotoxicity

PCA neurotoxicity after MAOI or 5-HT_2A antagonist pretreatment, PCA is different from MDMA neurotoxicity

#436

Biochem. Pharmacol.

1271

1996

J. E. Sprague

Lil

5-HT releasers review

5-HT releasers review, neurotoxicity from dopamine / 5-HT release, MMAI binding data, rat synaptosomes monoamines uptake inhibition data, MMAI rat brain slice 5-HT release data

#437

Drug Des. Disc.

299

1993

D. E. Nichols

Lil

MDMA neurotoxicity and MAO-B-I

MDMA neurotoxicity after the MAO-B-I deprenyl, rat brain paroxetine binding B_MAX and 5-HT (-metabolite) long term effects, rat brain acute radical formation markers

#438

J. Pharm. Exp. Ther.

273

667

1995

J. E. Sprague

Lil

glutathionyl-alpha-methyldopamine

2,5-bis-glutathionyl-alpha-methyldopamine (MDMA and MDA metabolite) neurotoxicity, rat behaviour data, rat monoamine (-metabolites) long term effects

#445

Eur. J. Pharmacol.

323

173

1997

R. T. Miller

Lil

fenfluramine

PMMA

PMMA and amphetamine, DOM, PMA, MDMA, 3,4-DMA, fenfluramine, alpha-ethyl PMMA analog, rat drug discrimination data (PMMA), generalization only to MDMA and (S)-MDMA

#422

Pharmacol. Biochem. Behav.

151

1997

R. E. Glennon

Lil

fenfluramine

fenfluramine effects in human, reporting of ant-aggressive and sedating effects and peacefule, tolerant, friendly, affable, compliant, benevolent, and calm up feelings

#424

J. Psychopharmacol.

1995

A. J. Bond

Lil

fenfluramine

neurotoxic (+)-fenfluramine pretreatment on rat drug discrimination data (MDMA)

#427

Pharmacol. Biochem. Behav.

455

1996

L. E. Baker

Lil

fenfluramine

serotonergic drugs, Fawn Hooded strain rat drug discrimination data (fenfluramine)

#448

Life Sci.

PL 83

1996

M. D. Schechter

Lil

piperazines

subst. benzylpiperazines

MDMA neurotoxicity after coadministration with H-, p-Cl-, p-MeO-, and p-NO₂-3,4-methylendioxy-benzylpiperazine, rat 5-HT (-metabolite) long term effects, rat 5-HT tarnsporter binding data (6-nitroquipazine)

#439

Brain Res.

590

341

1992

K. Hashimoto

Lil

subst. benzylpiperazines

MDMA acute effects after coadministration with H-, p-Cl-, p-MeO-, and p-NO₂-3,4-methylendioxy-benzylpiperazine, rat 5-HT (-metabolite) acute effects, rat synaptosomes 5-HT uptake inhibition data

#444

Neurosci. Lett.

152

1993

K. Hashimoto

Lil

subst. benzylpiperazines

MDMA tissue distribution time course after pretreatment with monoamine uptake inhibitors and methylendioxybenzylic compounds incl. piperonylpiperazine

#443

Eur. J. Pharmacol.

228

247

1992

K. Hashimoto

Lil

piperonylpiperazine

MDMA neurotoxicity after coadministration with piperonylpiperazine, N,alpha-piperonylamine, paroxetine and 6-nitroquipazine, rat 5-HT (-metabolite) long term effects, rat 6-nitroquipazine B_MAX binding data long term effect

#449

Eur. J. Pharmacol.

228

171

1992

K. Hashimoto

Lil

MDMA and 5-HT₃

MDMA and 5-HT₃ antagonists

MDMA blocks MDL72222 (5-HT₃ antagonist) conditioned place preference

#446

Pharmacol. Biochem. Behav.

509

1991

E. J. Bilsky

Lil

MDMA and 5-HT antagonists

5-HT₃ antagonists antagonize MDMA stimulus, 2-Me-5-HT and various 5-HT antagonists, rat drug discrimination data (MDMA),

#447

Pharmacol. Biochem. Behav.

1099

1992

R. A. Glennon

Lil

hydroxylamines

aryl-ethyl-hydroxylamines

subst. amphetamine and AMT hydroxylamine analogs, pharmacological data, synth. from ketone, via oxime with hydroxylamine and reduction with H₂ / Pdo / EtOH / HCl

#440

J. Med. Chem.

100

1965

F. Benington

Lil

indolyl-ethyl-hydroxylamines

ring,alpha-subst. tryptamine hydroxylamine analogs from nitroalkanes (from gramines and nitroalkanes) with Zn / NH₄Cl, yields 57% - 75%, or from indolylacetone with hydroxylamine and reduction with H₂ / Pdo / EtOH / HCl, yield 24%

#441

J. Chem. Soc.

7179

1965

A. Cohen

Lil

indolyl-ethyl-hydroxylamines

patent Brit. 990,092, for paper see #0441

#443

2959

1965

A. Cohen

Lil

AMT (hydroxylamine) analogs

AMT (hydroxylamine) analogs, metabolism of hydroxylamines to amines, guinea pig liver MAO inhibition (5-HT) data, mouse tremor time course, mouse pharmacological data, rat tissue distribution and metabolism data

#442

Biochem. Pharmacol.

481

1966

A. W. Lessin

Lil

receptor binding site

5-HT_2A receptor model, fitting of ketanserin-like antagonists and DOM-like agonists, correlation between predicted and experimental affinities

#451

Arch. Pharm.

328

577

1995

H.-D. Höltje

Lil

5-HT_2A receptor aromatic residue mutations and agonist binding, 5-HT, bufotenine, DOM, and alpha-Me-5-HT binding (ketanserin) and IP accumulation data

#452

J. Pharm. Exp. Ther.

259

1997

B. L. Roth

Lil

5-HT_2A receptor TM3 Ser mutants and ligand amino substitutions, 5-HT, bufotenine, and LSD binding data (ketanserin)

#453

J. Biol. Chem.

271

14672

1996

N. Almaula

Lil

5-HT receptor models review

#454

J. Pharm. Pharmacol.

791

1995

Z. Chilmonczyk

Lil

5-HT_1A receptor model, fitting of antagonists and agonists

#460

Drug Des. Discov.

231

1994

W. Kuipers

Lil

5-HT_1Dbeta and 5-HT_1E receptor TM6 residue mutations and chimeras, 11 ligands binding data (5-HT)

#461

J. Neurochem.

2096

1996

E. M. Parker

Lil

differences between 5-HT_2A and 5-HT_2C receptors, agonists and antagonists (+GTP) 5-HT_2A and 5-HT_2C receptor binding data (DOI, 5-HT, mesulergine, ketanserin), binding states

#463

Mol. Pharmacol.

328

1992

S. Leonhardt

Lil

psilocin and bufotenin hum. vs. rat 5-HT_2A binding data (ketanserin)

#464

Med. Chem. Res.

1993

T. K. Gallaher

Lil

N1 substitution species variation 5-HT_2A binding data

cloning of 5-HT₂ receptors

cloning and distribution of a rat, hum. and mouse 5-HT_2C receptor splice variant

#455

Mol. Pharmacol.

799

1996

H. Canton

Lil

cloning of a gene involved in 5-HT receptor signal transduction or expression

#456

FEBS Lett.

401

252

1997

S. Ohya

Lil

cloning and distribution of the hum. 5-HT_2B receptor, 13 agonists and 22 antagonists binding data (DOI)

#458

FEBS Lett.

352

393

1994

D.-S. Choi

Lil

5-HT receptor nomenclature, especially 5-HT_1B, 5-HT_1Dalpha, and 5-HT_1Dbeta

#459

TIPS

103

1996

P. R. Hartig

Lil

binding theory

5-HT_2A receptor high affinity binding vs. efficacy, TM6 F340L mutation, bufotenine, DMT, 5-MeO-DMT, 5-HT, alpha-Me-5-HT, DOM, (-)-DOB, DOI, and quipazine binding (ketanserin) and IP accumulation data, ternary state receptor model

#457

J. Pharm. Exp. Ther.

280

576

1997

B. L. Roth

Lil

DMT: agonist or antagonist

DMT as putative rat 5-HT_1A agonist and rat 5-HT_2A antagonist, DMT (+GTP) rat 5-HT1A (-OHDPAT) and rat 5-HT_2A (ketanserin) binding data, AC inhibition and IP accumulation data

#462

Biochem. Pharmacol.

1739

1991

A. V. Deliganis

Lil

chromatography

PRISMA solvent optimization

PRISMA method for TLC solvent optimization

#466

J. Planar Chrom.

336

1988

S. Nyiredy

Lil

vacuum liquid chromatography

vacuum liquid chromatography for simple, fast, and inexpensive separation of closely related compounds

#538

J. Nat. Prod.

934

1986

J. C. Coll

Lil

vacuum liquid chromatography

vacuum liquid chromatography for simple, fast, and inexpensive separation of closely related compounds

#539

J. Nat. Prod.

892

1986

S. W. Pelletier

Lil

PTC imine C-alkylations

glycine imines alkylations

imines from glycine ester and 4-Cl-benzaldehyde or benzophenone, TBA-HSO₄ and TEBA-Cl, various alkylhalogenides, aq. NaOH or ground KOH, CH₂Cl₂

#477

Tet. Lett.

4255

1982

M. J. O'Donnell

Lil

alpha-Me-DOPA analogs

imines from alanine ester or O-benzyltyrosines esters and 4-Cl-benzaldehyde or mesityldehyde (against Pictet-Spengler), TBA-Br and TEBA-Cl, various benzyloxylated benzylchlorides or methyl iodide, ground KOH, CH₃CN or CH₂Cl₂

#478

Tet. Lett.

4259

1982

M. J. O'Donnell

Lil

alpha-Me-histidine

imines from alanine or tosyl-histidine ester and 4-Cl-benzaldehyde, TBA-Br, acetoxymethyl-toyslimidazoline or methyl iodide, ground KOH, CH₃CN

#479

Synth. Commun.

1157

1989

M. J. O'Donnell

Lil

stereoselective alpha-Me-AA

imines from alanine-tert-butylester and subst. benzaldehyde, N-Bz. chinchoninium chloride catalyst, subst. arylmethyl bromides, various bases (NaOH, KOH or K₂CO₃), CH₂Cl₂

#480

Tet. Asym.

591

1992

M. J. O'Donnell

Lil

alpha-alkyl-alanines and -phenylalanines

imines from alanine-tert-butylester and subst. benzaldehyde, N-Bz. chinchoninium chloride catalyst, subst. arylmethyl bromides, various bases (NaOH, KOH or K₂CO₃), CH₂Cl₂

#481

J. Am. Chem. Soc.

111

2353

1989

M. J. O'Donnell

Lil

4-subst. 2-oxazolin-5-ones alkylation

4-monosubst. 2-oxazolin-5-ones from various AA, TBA-Br, alkyl halogenides, aq. Na₂CO₃, CH₂Cl₂

#482

Synth.

763

1984

M. L. Gelmi

Lil

AA imines alkylation and pK_a

imines from glycine and alanine esters and benzaldehyde, 4-Cl-benzaldehyde or benzophenone, TBA-Br, benzylbromide, aq. NaOH or ground K₂CO₃, CH₂Cl₂, imines pK_a

#483

J. Am. Chem. Soc.

110

8520

1988

M. J. O'Donnell

Lil

imino-acetonitrile alkylation

imine from amino-acetonitrile and benzophenone, TEBA-Cl, various alkylbromides, benzylchloride, or dimethyl sulfate, aq. NaOH, toluene

#484

Tet. Lett.

4625

1978

M. J. O'Donnell

Lil

AA alpha-alkylations

imines from glycine and alanine esters and benzaldehyde, TEBA-Cl, various alkylhalogenides, KOH and K₂CO₃, CH₃CN or CH₂Cl₂, mechanism of PTC alkylation, base mixture optimization

#485

Tet.

5343

1988

J. Yaozhong

Lil

AA alpha-alkylations

imines from glycine and alanine esters and 4-Cl-benzaldehyde or benzophenone, TBA-Br, various alkylhalogenides, K₂CO₃, CH₃CN

#486

Synth.

313

1984

M. J. O'Donnell

Lil

3-fluoro-phenylalanine from glycine

imines from glycine esters and benzophenone, TBA-HSO₄, alpha-F-benzylbromide, aq. NaOH, CH₂Cl₂

#487

Tet. Lett.

3067

1985

M. J. O'Donnell

Lil

non-PTC imine C-alkylations

glycine ethyl ester alkylation

imines from glycine or alanine ethyl esters and benzaldehyde, anion with LDA / hexamethyl phosphoramide or t-BuONa, alkylation with octyl iodide, butyl bromide, isopropyl iodide, aldehydes and ketones from AA reduction with LiAlH₄ and periodic acid cleavage, Michael addition of alkenes to imine

#496

J. Org. Chem.

3491

1976

G. Stork

Lil

alanine ester alkylation

benzylidene alanine anion with LDA, alkylation with phtalimidoyl-alkyl iodides

#509

J. Med. Chem.

1978

P. Bey

Lil

Trp : pivalaldehyde imine, oxazolidinone

imine from d-tryptophan and pivalaldehyde by stirring with NaOH and molecular sieves in MeOH for 20 h, esterification and cyclization to oxazolidinone, anion with LDA, alkylation with MeI, hydrolysis to (R)-alpha-Me-tryptophan

#510

J. Med. Chem.

5719

1995

L. Zhang

Lil

isocyano-Boc-Trp ester alkylation

isocyano analog from formamido-Boc-Trp, anion with LDA, alkylation with alkyl halogenides, hydrolysis, no reaction of benzylidene-Trp with higher alkyl halogenides or of Boc-Trp ester benzophenone imine or Trp amidine ester with even MeI

#512

Synth.

465

1990

D. Pettig

Lil

isocyano AA ester alkylation

isocyano-ester analogs of alanine, phenylglycine, and phenylalanine, anion with NaH at RT, alkylation with alkyl dibromides, hydrolysis, cyclization to proline-type AA

#513

Chem. Pharm. Bull.

1931

1979

H. Yasuo

Lil

arachidonate 2-alkylation

methyl arachidonate, anion with LDA, alkylation with alkyl iodide

#514

Life Sci.

2041

1995

I. B. Adams

Lil

alanine ester alkylation

imine from alanine and benzaldehyde, anion with NaH at RT or LDA, alkylation with var. alkyl halogenides

#515

Tet. Lett.

1455

1977

P. Bey

Lil

alpha-halogenemethyl-AA

imines from Ala, Lys, Orn, Met, Phe, Tyr, 3,4-diOH-Phe, His, or Arg ester, anions (stable at RT) with LDA or NaH / hexamethylphosphoramide, alkylation with MeI, CH₂BrCl, MeClF₂, hydrolysis

#516

J. Org. Chem.

2732

1979

P. Bey

Lil

AA imidine ester alkylation

imidine esters from AA with DMF dimethyl acetal in one step, anion with LDA or tBuOK, alkylation with alkyl halogenides or alkenes, hydrolysis, chelate mechanism

#517

J. Org. Chem.

2639

1977

J. J. Fitt

Lil

tryptophan- or tryptamine-imines

tryptophan ester imines

tryptophan ester imine from tryptophan methyl ester, isovaleraldehyde and molecular sieve, imine acylation with prolyl chloride.

#488

Tet. Lett.

3235

1986

M. Nakagawa

Lil

tryptophan - acetone imine

imine from tryptophan and acetone under reflux for 40 h as a not isolated intermediate

#495

Het.

1987

M. F. Braña

Lil

AA / arom. ketone imines

AA imines from AA incl. Trp and Phe and 2-OH-acetophenone, -butyrophenone, 2,2'-OH-benzophenone, 2,2'-MeO-benzophenone, or 2,4-OH-benzophenone

#498

J. Chem. Soc. C

411

1968

A. F. Al-Sayyab

Lil

tryptamine / cycloalkanone imines

imines from tryptamine and cycloalkanones (C5-C8, TH-pyranon, TH-thiopyranon, piperidinon) by refluxing in benzene with water trap for 5 h, Pictet-Spengler reaction to beta-carbolines with H₂SO₄ or polyphosphoric acid

#499

J. Het. Chem.

373

1993

J. G. Rodríguez

Lil

tryptamine : naphtaldehyde imines

imines from tryptamine and 1- or 2-naphtaldehydes or 4-pyridaldehyde by precipitation after 10 min reflux in MeOH, Pictet-Spengler reaction to beta-carbolines with HCl, imine reductions with H₂, Pd/C, EtOH

#500

Can. J. Chem.

2963

1967

B. T. Ho

Lil

tryptamine : subst. benzaldehyde imines

imines from tryptamine and 3-Meo-, 4-Meo- or 4-dimethylamino-benzaldehyde by precipitation after 90 min reflux in MeOH, Pictet-Spengler reaction to beta-carbolines with HCl, imine reductions with NaBH₄ in EtOH, N-2-phenoxy- and N-benzyl-tryptamides and -amines

#501

Coll. Czech. Chem. Commun.

629

1963

M. Protiva

Lil

alpha-hydroxymethyl-tryptamine

imine from alpha-hydroxymethyl-tryptamine and benzaldehyde by refluxing in benzene and evaporation, alpha-hydroxymethyl-tryptamine from tryptophan ester wit LiAlH₄

#502

Ber.

2290

1958

H. Hellmann

Lil

T / Trp ester imines, trimethylene Trp

imines from tryptamine or tryptophan ester and (4-Cl or 4-NO₂-) benzaldehyde or alkanals by stirring in CH₂Cl₂ / Et₂O / MgSO₄, Z-Trp ester formimine in situ from trimethylene tri(Z-Trp ester) and ZnCl₂,

#503

Tet.

397

1993

H. Waldmann

Lil

tryptophan ester aldehyde imines

imine from tryptophan ester and benzaldehyde by refluxing in benzene with water trap, conditions and mechanism of Pictet-Spengler reaction to beta-carboline

#504

J. Org. Chem.

2699

1984

M. Jawdosiuk

Lil

tryptamine : acetone imines

imines from (5-Meo-) tryptamine and acetone by refluxing in benzene with cat. pTsOH and water trap, 6-MeO-tryptamine cyclized to beta-carboline, imine cyclization with POCl₃, Pictet-Spengler mechanism

#505

J. Org. Chem.

2864

1964

J. B. Hester

Lil

tryptamine : benzaldehyde imine reaction

mechanism of Pictet-Spengler cyclization of benzylidene tryptamine with Lewis acids

#506

Het.

801

1992

T. Kawate

Lil

tryptamine : benzaldehyde imine

imine from tryptamine-HCl and benzaldehyde by refluxing in H₂O / MeOH and NaOH addition, Pictet Spengler reaction to beta-carboline with HCl

#507

Anal. Chem.

1536

1973

J. M. Lisy

Lil

AA ester : isobutyraldehyde imines

imines from all AA esters and isobutyraldehyde bisulfite addition product, reduction with Zn / HCl, AA esters from AA with MeOH, thionyl chloride, not checked for Pictet-Spengler reactions

#508

Anal. Chem.

1910

1968

J. W. Davis, JR.

Lil

beta-carbolines

beta-carbolines from 5-MeO-, 5-MeO-N-Me-, 5-BzO-, 6-BzO-, and 7-BzO-tryptamine and acetaldehyde, alpha-ketoglutaric acid, and pyridoxal, 5-MeO-N-Me-tryptamine from 5-Meo-N-Tos-tryptamine and MeI

#518

J. Med. Chem.

135

1964

R. G. Taborsky

Lil

imine N-alkylation

AA ester imine N-alkylation

AA ester imines and amidines N alkylation with dimethylsulfate or dimethyltriflate in CH₂Cl₂ or toluene

#489

Tet. Lett.

3651

1984

M. J. O'Donnell

Lil

benzaldehyde-PEA methylation

imine from phenylethylamine and benzaldehyde (or vanilline), imine N-methylation with MeI

#491

Ann.

364

362

1909

H. Decker

Lil

alkylimines methylation

imines from alkylamine and benzophenone, imine N-methylation with MeI

#492

Compt. Rend. Acad. Sci.

184

1338

1927

M. Sommelet

Lil

benzylidenealkanes alkylation

imines from lower alkylamines and benzaldehyde, imine N-methylation with dimethyl- or diethylsulfate

#493

Acta Chem. Scand.

1109

1961

K. A. Jensen

Lil

bis-benzylidene-alkanes dimethylation

imines from alkyldiamines and benzaldehyd, imine N-methylation with dimethylsulfate, yields 85 - 99%

#494

Synth.

303

1980

F. Devínsky

Lil

benzaldehyde-PEA methylation

imine from PEA and benzaldehyde by distillation of H₂O and educts without solvent, imine N-methylation with MeI in Et₂O, dissolution in conc. HCl and steam destillation of benzaldehyde without Pictet Spengler reaction (?)

#511

Arch. Pharm.

501

1924

S. Osada

Lil

MeEtNH

MePrNH

MePrNH from tripropyl-trimethylene-triamine in quantitative yield, trimethyl-, triethyl-, and tripropyl-trimethylene-triamine from aq. formaldehyde and aq. alkylamine solutions in quantitative yields

#490

J. Chem. Soc.

1490

1931?

J. Graymore

Lil

unsym. sec. Alkylamines

electrochemical reductive amination of various aldehydes with primary amines, good yields

#197

J. Org. Chem. USSR (Engl.Transl.)

374

1992

Yu. D. Smirnov

Lil

triazine

hexahydro-1,3,5-triazine from phenylglycine and formaldehyde with NaOH in benzene / H2O

#520

Chem. Pharm. Bull.

3985

1987

O. Nakaguchi

Lil

stimulants

pipradol and benzhydrylpiperidine analogs

morpholine, pyrrolidyl, and azacycloheptane analogs of pipradol and benzhydrylpiperidine, morpholines are the most active compounds

#530

J. Org. Chem.

2834

1961

S. O. Winthrop

Lil

pipradol analogs

phenyl substituted and and heterocyclic pipradol analogs, mouse motor activity data

#533

J. Am. Chem. Soc.

472

1957

F. J. McCarty

Lil

benzhydrol-pyridines

benzhydrol-pyridines from 3-Br-pyridine, BuLi, and ( p -Me/F/-Ph)₂CO, or from 1-Br-2-MeO-benzene, Mg, and ethyl nicotinate, reduction with H₂ / PtO₂ / EtOH / HCl to benzhydryl-pyridines, benzhydryl-pyridines from PhCl and pyridine-3-carbaldehyde with conc. H₂SO₄

#558

14171e

1966

R. H. Mizzoni

Lil

N-acyl-2-diphenylmethyl-piperidines

2-diphenylmethyl-piperidines N-acylation

#559

5548g

1961

K. Hoffmann

Lil

2-diphenylmethyl-pyrrolidine

2-diphenylmethyl-pyrrolidine from PhBr, Mg, and proline ethyl ester in anisole, yield 23%, reduction with 1. HI in AcOH 2. Na₂S₂O₃, yield 98%, rat activity data, ref. patent Fr. M. 3,638 1965

#560

106375m

1969

Roussel-UCLAF

Lil

2-diphenylmethyl-pyrrolidine

2-diphenylmethyl-pyrrolidine from proline via N-ethoxycarbonyl-proline ethyl ester with ClCO₂Et, reaction with PhMgBr, and reduction with H₂ / Pd/C / MeOH, total yield 67%

#561

Tet. Asym.

149

1997

D. J. Bailey

Lil

OH-pipradols

2-diphenylmethyl-3-OR-piperidines from pyridinols with H₂ / Raney Ni, NaOH / dioxane, N-Ac-, N-Me, N-Bz, N-PhCO, N-BzCO, O-Me, O-Ac, O-EtCO, O-Me₂NCO, mono- p -Cl, mono- p -MeO, cyclohexyl, and benzyl analogs, rat motor activity data

#562

J. Med. Chem.?

792

1968

L. A. Walter

Lil

heterocyclic pipradol and diphenylmethyl-piperidine analogs

thienyl, pyrodyl, and piperidyl analogs of pipradol and 2-diphenylmethyl-piperidine, C-alkylated and NC,N-alkylated derivatives, rat motor activity data

#563

Helv. Chim. Acta

134

1955

J. Heer

Lil

2-diphenylmethyl-piperidine

2-diphenylmethyl-piperidine, rat motor activity data

#564

Experientia

261

1654

J. Tripod

Lil

subst. 2-diphenylmethyl-piperidines

subst. 2-diphenylmethyl-piperidines and analogs, rat motor activity data

#565

Helv. Chim. Acta

2133

1954

E. Sury

Lil

unsaturated 2-diphenylmethyl-piperidines

subst. 2-diphenylmethyl-piperidines and analogs, reduction with Na / BuOH or AmOH or with H₂ / PtO or Ni, poor rat motor activity compared to 2-diphenylmethyl-piperidine

#566

Helv. Chim. Acta

728

1955

E. Sury

Lil

1-Me-2-diphenylmethyl-piperidine via radical mech.

1-Me-2-diphenylmethyl-piperidine from N-Me-6,6-diphenyl-5-hexenamine with 1. 1-oxa-2-oxo-3-thiazolinium chloride, yield 51% 2. Bu₃SnH, light, and I₂, yield 73%

#567

J. Am. Chem. Soc.

117

11124

1995

J. H. Horner

Lil

diarylmethanols reduction with NaBH₄ in TFA

subst. diarylmethanols reduction to diarylmethanes with NaBH₄ in TFA, excellent yields

#568

Synthesis

172

1977

G. W. Gribble

Lil

2-diphenylmethyl-pyrrolidine

2-diphenylmethyl-pyrrolidine from proline via B-Bz-proline ester with 1. SOCl₂ / EtOH, 2. DCC, BzOH, yield 75%, N-Bz-pipradol with PhMgX, yield 75%, 2-diphenylmethyl-pyrrolidine with 1. Li / liquid NH₃, yield 72% 2. H₂ / Pd/C / EtOH, yield 91%

#569

Bull. Soc. Chim. Belg.

691

1988

D. Enders

Lil

subst. 2-benzhydrylpiperidines

subst. 2-benzhydrylpiperidines from diphenylmethyl-pyridines, benzhydryl-pyridines, or 1,1-diphenyl-5-CN-2-pentanone with with H₂ / cat, from piperidyl-benzhydrol with LiAlH₄, or from diphenyl-pyridyl-acetic acid or amide with H₂SO₄, ecpecially active are 1-Me-2-benzhydryl-piperidine and 2-(Ph- p -Cl-Ph-methyl)-piperidine, patent ref. Ger. 1,095,280

#570

2197d

1962

K. Hoffmann

Lil

(R)- and (S)-alpha-cyclohexyl-PEA and -N-Me-PEA via (1-Me-) 2-cyclohexyl-4-Ph-1,3-oxazolidine from alpha-phenylglycinol and cyclohexyl-carbaldehyde, reaction with PhMgCl, debenzylation with H₂ / Pd/C / AcOH, analgesic activity data, potent amphetamine activity of S-isomer

#571

Chem. Pharm. Bull.

2071

1986

H. Takahashi

Lil

rac. alpha-cyclohexyl-PEA

rac. alpha-cyclohexyl-PEA and unsaturated analogs via phenylacetylcyclohexene from phenylacetylchloride and cyclohexene, benzylcyclohex-1-enyl ketoxime with NH₂OH, benzyl-cyclohexyl-ketone with H₂ / Pd/C / EtOH / HCl, oxime, reduction with LiAlH₄, rat anorexia and motor activity data, mice LD₅₀ data, medium rat motor activity inhibition at ¹ /₁₀ LD₅₀

#572

Drug. Res.

1561

1978

P. Ghosh

Lil

methamphetamine from imine and PhMgCl

methamphetamine from methylamine, acetaldehyde, and BzMgCl, yield ca. 40%

#573

Gazz. Chim. Ital.

318

1947?

V. Evdokìmoff

Lil

stimulants

thiamorpholinyl pipradol analog

thiamorpholinyl pipradol analog from thiamorpholin-2-carboxylate and Ph-MgBr, mouse motor activity data

#536

J. Med. Chem.

553

1960

D. Belleau

Lil

2-amino-1,2-dihydronaphtalene

2-amino-1,2-dihydronaphtalene, mouse motor activity data

#537

J. Med. Chem.

535

1982

B. A. Hathaway

Lil

psychotomimetics review

extensive psychotomimetics review, many references, stimulant reviews in the same volume

#544

Handbook of Psychopharmacology, Stimulants, Ed. L. L. Iversen, Plenum Press, NY

243

1987

A. T. Shulgin

Lil

indole Grignard

indole Grignard, indolylacetone

3-allyl-indole from indolyl-MgBr and allyl bromide, yield 70%, 3-indolylacetaldehyde, 3-indolylacetone from IAA with 1. Ac₂O / NaOAc, yield 49% 2. MeONa, yield 55%

#547

J. Chem. Soc.

3172

1952

J. B. Brown

Lil

blockers

4-piperidyl-benzhydrol blocks LSD

(4-piperidyl)-diphenyl-methanol blocks LSD effects in human

#545

Science

121

208

1955

H. D. Fabing

Lil

DMT and LSD blockers

diethyl-alkyamides as blockers and enhancers of DMT, DOM, and mescaline activity, rat Bovet-Gatti profile activity data, enormous doses used, ref. to: LSD blocker THPC: J. R. Smythies (Ed.) The Mode of Action of Psychotomimetic Drugs, NRP Bull. 8, 1 1970

#343

Eur. J. Pharmacol.

270

1972

J. R. Smythies

Lil

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Lilienthal'sPharmacological & ChemicalReferences

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Lilienthal's
Pharmacological & Chemical
References