Isomeric monomethyl ether derivatives of (RS)-9,10-dihydroxyaporphine ("isoapomorphine") as possible products of metabolism by catechol-O-methyltransferase.
The isomeric monomethyl ether derivatives of (RS)-9,10-dihydroxyaporphine ("isoapomorphine") were synthesized unequivocally as possible metabolites in catechol-O-methyltransferase (COMT) mediated O-methylation reactions. In vitro incubation studies revealed that isoapomorphine is not a substrate for the COMT using experimental conditions under which apomorphine (10,11-dihydroxyaporphine) is converted in high yield into its 10-methyl ether, apocodeine. The in vivo dopaminergic inactivity of isoapomorphine (as compared with that of apomorphine) seems to be due to factors other than metabolic inactivation by COMT.
Cannon
J G
JG
Division of Medicinal and Natural Products Chemistry, College of Pharmacy, University of Iowa, Iowa City 52242.
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D001058:Apomorphine / Q000494:pharmacology / Q000031:analogs & derivatives; D001060:Aporphines / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D002394:Catechol O-Methyltransferase / Q000378:metabolism*; D055598:Chemical Phenomena; D002621:Chemistry; D004987:Ethers; D008745:Methylation; D008968:Molecular Conformation; D015394:Molecular Structure; D013379:Substrate Specificity
D001060:Aporphines; D004987:Ethers; C008175:isoapomorphine; D002394:Catechol O-Methyltransferase; D001058:Apomorphine