Potential Reserpine Analogues: Part I. Derivatives of Tryptamine

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Abstract
The six amides, cis-N-(3-indolylethyl)-3-methoxycyclohexanecarboxylic acid amide (II), cis-N-(3-indolylethyl)-N-3-methoxycyclohexylmethyl-acetamide (IV), N-(3-indolylethyl)-3,4,5-trimethoxybenzamide (V), N-(3-indolylethyl)-3,4-dimethoxyphenylacetamide (VII), 3-indolyl-N-(3,4-dimethoxyphenethyl)acetamide (VIII) and 4-methoxycyclohexyl-acetotryptamide (X), have been prepared. II has been reduced to cis-N-(3-methoxycyclohexylmethyl)tryptamine (III); VII and VIII have both been reduced to N-(3,4-dimethoxyphenethyl)tryptamine (IX), X has been reduced to N-(4-methoxycyclohexylethyl)tryptamine (XI) and V to N-(3,4,5-trimethoxybenzyl)tryptamine (VI). Nine of the compounds, II-VI, VIII-XI, were compared with reserpine for their power to potentiate barbiturate hypnosis in mice, and to deplete the 5-hydroxytryptamine content of rat brain. Only compound (IV) was active in both tests, having about one-thirteenth the activity of reserpine. Compound (V) was about one-eighth as active as reserpine in producing potentiation of barbiturate hypnosis.