[On separation of isomeres, structural elucidation and pharmacological characterization of 1-(m-methoxyphenyl)-2-(dimethylaminomethyl)-cyclohexan-1-ol (author's transl)].
1-(m-Methoxyphenyl)-2-(dimethylaminomethyl)-cyclohexan-1-ol (L 201) was split into the cis- and trans-isomers and the conformations of the two isomers were determined by 13C-NMR-spectroscopy. Molecule models showed that both conformeres were similar to the geometrical structure of morphine. The adaptation of the morphine structure was better with the more active trans-isomer than with the cis-isomer. Tramadol, the trans-isomer, was separated into its optical antipodes. When tested for analgesia in the electro-stimulation test with mice, all compounds showed analgetic activity. The trans-isomer was more active than the cis-isomer and the (+)-form of the trans-isomer was more active than the (--)-form. Given by s.c. route, the (+)-transisomer E 382 was 1/3 as active as morphine. However, the Straub-tail reaction and the withdrawal jumping tests yielded more favourable results with L 201 and tramadol than with E 382.
D000700:Analgesics; D000818:Animals; D003511:Cyclohexanols / Q000494:pharmacology*; D004347:Drug Interactions; D005260:Female; D007536:Isomerism; D007928:Lethal Dose 50; D051379:Mice; D008968:Molecular Conformation; D009020:Morphine / Q000037:antagonists & inhibitors / Q000494:pharmacology; D011930:Reaction Time / Q000187:drug effects; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014147:Tramadol / Q000032:analysis / Q000494:pharmacology*
D000700:Analgesics; D003511:Cyclohexanols; D014147:Tramadol; D009020:Morphine
Uber die Isomerentrennung, Strukturaufklärung und pharmakologische Charakterisierung von 1-(m-Methoxyphenyl)-2-(dimethylaminomethyl)-cyclohexan-1-ol.