Author Topic: SAR: Ring-Substituted N,N-Dialkyltryptamines  (Read 1346 times)

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SAR: Ring-Substituted N,N-Dialkyltryptamines
« on: April 27, 2003, 06:01:00 AM »
SAR Relationships in Potentially Hallucinogenic N,N-Dialkyltryptamines Substituted in the Benzene Moiety
Toni B. Kline, Frederick Benington, Richard D. Morin, John M. Beaton
J. Med. Chem.; 1982; 25(8); 908-913.

A series of N,N-dialkyltryptamines with methylthio or methylenedioxy substituents in the 4, 5, and 6 positions and methyl or isopropyl on the side-chain nitrogen has been synthesized. The behavioral pharmacology of these compounds showed them to possess Bovet-Gatti profiles characteristic of hallucinogens, and the 5-methylthio congener was the most potent. Binding studies a t [3H]LSD and [3H]5-HT sites demonstrated that no single structural feature correlated with binding or behavioral changes and suggest a complex mode of action for these potential hallucinogenic agents.



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(N-Cyclopropyl-) 5,6-Methylenedioxytryptamines
« Reply #1 on: May 21, 2004, 10:05:00 AM »
Synthesis and Characterization of 5H-1,3-Dioxolo[4,5-f]indoleethylamines
Douglas B. Grotjahn

J. Heterocyclic Chem. 20, 1031-1036 (1983)


Twelve new N,N-dialkylated-5,6-methylenedioxytryptamines and N-cyclopropyl-5,6-methylenedioxytryptamine were prepared as hybrids of known psychoactive phenylethylamines and tryptamines. Novel, more convenient syntheses of N-methyl- and N-benzylcyclopropylamine are described.


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Abramovitch Tryptamine Syntheses
« Reply #2 on: May 30, 2004, 02:21:00 PM »
Tryptamines, Carbolines, and Related Compounds. Part II.
A Convenient Synthesis of Tryptamines and ?-Carbolines.

R. A. Abramovitch and D. Shapiro

J. Chem. Soc. 4589-4592 (1956)


2,3-Dioxopiperidine 3-phenylhydrazone was cyclised under acid conditions to 1,2,3,4-tetrahydro-1-oxo-?-carboline. This was hydrolysed to tryptamine-2-carboxylic acid which was decarboxylated to tryptamine. The same reaction sequence with p-anisidine afforded a new route to serotonin. 5-Benzyloxytryptamine-2-carboxylic acid could not be decarboxylated to the base. The method also provides a route to the 1,2,3,4-tetrahydro-?-carbolines.
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Tryptamines, Carbolines, and Related Compounds. Part III.
1-Methyl- and 1,N-Dimethyl-tryptamines

R. A. Abramovitch

J. Chem. Soc. 4593-4602 (1956)


The scope of the synthesis of tryptamines from 1,2,3,4-tetrahydro-1-oxo-?-carbolines has been examined. Substituents in the benzene ring affect the ease of decarboxylation of the tryptamine-2-carboxylic acids, in the order OMe > Me > H > Cl > NO2; an explanation is suggested. Tetrahydro-oxocarbolines with dimethyl sulphate give the 9-methyl compounds from which the 1-methyltryptamines can be obtained; the amide group is unreactive but can be methylated by prolonged treatment with sodium hydride followed by methyl iodide, to give the 2,9-dimethyl compound in which the amide group now behaves normally, though it is resistant to alkaline hydrolysis. Acid hydrolysis leads to N,N'-dimethyltryptamine. Cyclisation of 2,3-dioxopiperidine 3-m-methoxyphenylhydrazone by formic acid gives a mixture of isomers, whereas ethanolic hydrogen chloride gives only the 7-methoxy-compound which, contrary to report, is hydrolysed normally to the amino-acid.