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Microbial Transformation of (−)-Δ1-3,4-trans-Tetrahydrocannabinol by Cunninghamella blakesleeana LENDER

✍ Scribed by Michael Binder

Publisher
John Wiley and Sons
Year
1976
Tongue
German
Weight
628 KB
Volume
59
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Incubation of (−)‐Δ^1^‐3, 4‐trans‐tetrahydrocannabinol (= Δ^1^‐THC; 3) with stationary cultures of Cunninghamella blakesleeana LENDER (Zygomycetales) (ATCC 8688a) yielded a number of metabolic conversion products. Isolation and structure elucidation of 6α‐hydroxy‐Δ^1^‐THC (4), the potential psychoactive 3″‐hydroxy‐Δ^1^‐THC (2) and 4″‐hydroxy‐Δ^1^‐THC (1), and the hitherto unknown metabolites 4″‐hydroxy‐6‐oxo‐Δ^1^‐THC (5), 4″, 6α‐dihydroxy‐Δ^1^‐THC (7) and 4″, 7‐dihydroxy‐Δ^1^‐THC (6) is described.

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## Abstract The metabolism of the non‐psychotropic cannabinoid (3__R__, 4__R__)Δ^1(7)^‐tetrahydrocannabinol (**1**) (=Δ ^1(7)^‐THC) was investigated in a rat liver microsomal preparation. The metabolites obtained from the incubation mixture were separated, purified and identified by ^1^H‐NMR. spect