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Nichols DE, Barfknecht CF, Long JP, Standridge RT, Howell HG, Partyka RA, Dyer DC.
“Potential psychotomimetics. 2. Rigid analogs of 2,5-dimethoxy-4-methylphenylisopropylamine (DOM, STP)”.
J Med Chem. 1974 Feb;17(2):161-6.
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Abstract
2-Amino-5,8-dimethoxy-6-methyl-l,2,3,4-tetrahydronaphthalene and 2-amino-4,7-dimethoxy-5-methylindan were prepared as rigid analogs of psychotomimetic phenylisopropylamines. Neither compound appeared to have psycho- tomimetic activity in rats. The effect of the aminotetralin derivative on 5-HT receptors in rat fundus strips and sheep umbilical arteries was also studied.
Early investigators studied P-amino-1,2,3,4-tetrahydro- naphthalene derivatives (aminotetralins) as lysergic acid congener. More recently, other workers have ap- proached aminotetralins as rigid analogs of psychoto- mimetic phenylisopropylamines.1f*6 Cooper and .Walters7 found that for mescaline-like activity, racemic trans-2- (3,4,5-trimethoxyphenyl)cyclopropylamine was much more potent than the cis isomer. Although this finding supports a transoid conformation of the ethylamine side chain of psychotomimetics at the receptor, it does not in- dicate the relative conformation of the side chain with re- spect to the plane of the aromatic ring. Since 2,5-di- methoxy-4-methylphenylisopropylamine (DOM, STP) is a potent hallucinogen, it was decided to prepare and test compounds 1 (DOM-AT) and 2 (DOM-AI) to determine whether they possessed similar activity. Compound 1 was prepared by two independent routes, outlined in Schemes I and 11, and the aminoindan derivative 2 was prepared as shown in Scheme III.
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