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Yim GKW, Nichols DE, Pfister WR. 
“Stereoselective Actions of Hallucinogen Analogues”. 
Pharmacologist. 1978;20(3):166.
Recently it was proposed that the structural relationship of LSD and phenethylamine type hallucinogens involved correspondence between the aromatic ring of the phenethylamines and the pyrrole portion of the indole nucleus in LSD (Nichols et al., Res. Bull. 2, 169, 1977). This hypothesis was used to predict that the active enantiomer of the rigid DOM analog (DMCPA) would possess the 1R, IS absolute configuration. DMCPA (trans2 - (2, 5 - dimethoxy-4-methylphenyl) - cyclopropylamine) was resolved into its 2 optical isomers. The levorotatory isomers (10 mg/kg) of DOM or DMCPA depressed spontaneous activity and induced forepaw treading, head twitches and ear scratching responses in mice. The dextro isomers were less active or inactive. In cats, limb flicks and head/body shakes were elicited by 1.25 mg/kg doses of the levo but not the dextro isomers. The absolute configuration of the levorotatory isomer of DMCPA was established as (-) 1R, 2S. A common receptor for binding of both typtamine and phenylethylamine hallucinogens, was suggested.
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