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Nichols DE. 
“Phenethylamine Hallucinogens: New Structural Analogy and Implications for Receptor Geometry”. 
Life Sci.. 1978;22(24):2165-70.
The stereoselectivity of phenethylamine hallucinogens was investigated. Behavioral effects were observed over a period of 30 min following i.p. injection of saline, racemic (10 mg/kg) or the (+) or (-) isomers (5 mg/kg) of 1-(2,5-dimethoxy-4-methylphenyl)-2aminopropane hydrochloride (DOM) or trans-2-(2,5-dimethexy-4methylphenyl)-cyclopropylamine hydrochloride (DMCPA) to adult male Swiss Webster mice (30-40 g). Behavior was also observed 60 min following administration of isomeric and racemic drugs (0.125 mg/kg i.p.) to adult mongrel cats (2-3.6 kg). Optical rotatory dispersion (ORD) curves were determined for the N-(5bromosalicylidene) derivatives of the (+) and (-) isomers of DMCPA and tranylcypromine (TC, SK+F). Scratching response of mice showed stereoselective activity for the (-) isomers of DOM and DMCPA. Doses < 80 mg/kg of (+) DOM did not produce scratching, while forepaw treading and the head twitch were elicited by both isomers of DOM and DMCPA. The limb flick and head/body shake responses of cats were elicited frequently by only the (-) isomers of DOM and DMCPA. The (+) isomers did not produce significant increases in any behavioral components studied. ORD curves showed that (-) DMCPA possessed the (-)-lR,2S configuration as does TC. Conclusion A new model of the hallucinogen receptor is proposed which suggests possible similarities between the structures of LSD and phenethylamine hallucinogens.
Notes # : Other authors? Pfister WR, Yim GKW
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