Biotransformation of 2-, 3-, and 4-methoxy-amphetamines by Cunninghamella echinulata.
1. Three methoxyamphetamine analogues have been incubated with Cunninghamella echinulata under different environmental and nutrient conditions. 2. The biotransformation of 4-methoxyamphetamine was inhibited by cobalt; the carbon source and other trace metals had no effect. The rate of biotransformation of 4-methoxyamphetamine and formation of 4-hydroxyamphetamine was greater in cultures incubated on 30 degrees angle brackets rather than flat. 3. Carbon monoxide, ethanol and quinidine had a significant effect on methoxyamphetamine metabolism. 4. Metabolism was influenced by the position of the methoxy side-chain and substrate concentration. In day 7 samples the relative order for biotransformation was 3- greater than 4- greater than 2-methoxyamphetamine. 5. O-Demethylation was the major metabolic route in the biotransformation of 4-methoxyamphetamine but occurred to a lesser extent with 3-methoxyamphetamine, and was only a trace pathway with 2-methoxyamphetamine. N-acetylation was a trace pathway.
Foster
B C
BC
Bureau of Drug Research, Sir Frederick Banting Research Centre, Ottawa, Ontario, Canada.
Litster
D L
DL
Lodge
B A
BA
D000662:Amphetamines / Q000493:pharmacokinetics*; D001711:Biotransformation / Q000187:drug effects; D050260:Carbohydrate Metabolism; D002248:Carbon Monoxide / Q000494:pharmacology; D000431:Ethanol / Q000494:pharmacology; D009090:Mucorales / Q000187:drug effects / Q000378:metabolism*; D011802:Quinidine / Q000494:pharmacology; D014131:Trace Elements / Q000494:pharmacology
D000662:Amphetamines; D014131:Trace Elements; C043935:N-desmethylmethoxyphenamine; C029870:3-methoxyamphetamine; D000431:Ethanol; D002248:Carbon Monoxide; D011802:Quinidine; C100230:4-methoxyamphetamine