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Ishii H, Hayashi M, Niwaguchi T, Nakahara Y. 
“Studies on Lysergic Acid Diethylamide and Related Compounds. IX. Microbial Transformation of Amides Related to Lysergic Acid Diethylamide by Streptomyces roseochromogenes”. 
Chem.Pharm.Bull.. 1979;27(12):3029-3038.
The microbial transformation of various congoners of LSD (t) by Streptomyces roseochromogenes was investigated. In general, microbial transformation of compounds lacking methylene at the w-1 position of the aminoalkyl chain of the amide function gave N-dealkylated products whereas those with a methyline at w-1 gave pairs of w-1 hydroxylated derivatives with the corresponding ketomethyl products. Hence (6) was oxidized to (7) whereas (8) gave mixture of (18-20) and (10) afforded a mixture of (21-23). (13) Underwent microbial oxidation to (15). LSD (1) itself was trasformed into (2-4). Those products were assigned the structure shown by means of mass, IR, UV and NMR spectrometry, as well as by Jones oxidation and NaBH4 production of the metabolites. The predominant formation of (19) from oxidition of (8) indiciited the stereospecificity of the w-1 hydroxylation. (13) Was prepared by reaction of (+)-lysergic acid (12) with diallyamine in a solution of HMPA/MeCN containing triphenylphosphite and imiditzole reaction that also yielded (14). An analogous reaction with allylamine yieded (15) and (16).
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