Preparation and pharmacological evaluation of enantiomers of certain nonoxygenated aporphines: (+)- and (-)-aporphine and (+)- and (-)-10-methylaporphine

• Published in: Journal of medicinal chemistry Vol. 36; no. 10; pp. 1316 - 1318
• Main Authors: Cannon, Joseph G, Raghupathi, Revathi, Moe, Scott T, Johnson, Alan K, Long, John Paul
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 14.05.1993; Amer Chemical Soc
• Subjects: Animals; Aporphines - chemical synthesis; Aporphines - chemistry; Aporphines - pharmacology; Chemistry; Chemistry, Medicinal; Dopamine Agents - chemical synthesis; Dopamine Agents - pharmacology; Exact sciences and technology; Guinea Pigs; Hemodynamics - drug effects; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Life Sciences & Biomedicine; Muscle Contraction - drug effects; Muscle, Smooth - drug effects; Organic chemistry; Pharmacology & Pharmacy; Preparations and properties; Rats; Receptors, Dopamine - drug effects; Receptors, Serotonin - drug effects; Science & Technology; Stereoisomerism; Structure-Activity Relationship; RECEPTORS; Vertebrata; Mammalia; Guinea pig; Serotoninergic receptor; Structure activity relation; Nitrogen heterocycle; Dopamine receptor; Animal; Enantiomer; Rodentia; Aromatic compound; Tetracyclic compound
• ISSN: 0022-2623; 1520-4804
• DOI: 10.1021/jm00062a002

The subject compounds were prepared as a part of a continuing structure-activity study of the contrasting actions (agonism-antagonism) of (+)- and (-)-11-hydroxy-10-methylaporphine at serotonin (5-HT1A) receptors. None of the targeted nonoxygenated aporphine derivatives demonstrated significant activity in assays for any effects at serotonin 5-HT1A receptors. It is concluded that, in the aporphine series, serotonergic agonist or antagonism requires an alkyl group ortho to a phenolic OH group in the A ring.