Harvey D J, Martin B R, Paton W D
J Pharm Pharmacol. 1977 Aug;29(8):482-6. doi: 10.1111/j.2042-7158.1977.tb11373.x.
In vivo liver metabolites of delta1-tetrahydrocannabinol (delta1-THC) were examined with a gas chromatograph--mass spectrometer--computer system as trimethylsilyl (TMS), [2H9]TMS and methyloxime-TMS derivatives. In addition to the reported monohydroxy, acid, and hydroxyacid metabolites, the following multiply substituted metabolites were identified: 2'',7-, 3'', 7-, and 6beta,7-dihydroxy-delta1-THC; 2'',6alpha,7-, and 3'',6alpha,7-trihydroxy-delta1-THC; 2''-, 3''-, and 7-hydroxy-6-oxo-delta1-THC, and 2'',7- and 3'',7-dihydroxy-6-oxo-delta1-THC. The ketones and hydroxyacids were reduced to common alcohols with lithium aluminium deuteride and the number of deuterium atoms in the product was used to distinguish the metabolic alcohols from those produced by reduction.
利用气相色谱-质谱-计算机系统，将δ1-四氢大麻酚（δ1-THC）的体内肝脏代谢产物作为三甲基硅烷基（TMS）、[2H9]TMS和甲基肟-TMS衍生物进行检测。除了已报道的单羟基、酸和羟基酸代谢产物外，还鉴定出以下多重取代代谢产物：2'',7-、3'',7-和6β,7-二羟基-δ1-THC；2'',6α,7-和3'',6α,7-三羟基-δ1-THC；2''-、3''-和7-羟基-6-氧代-δ1-THC，以及2'',7-和3'',7-二羟基-6-氧代-δ1-THC。用氘代氢化铝锂将酮和羟基酸还原为常见的醇，并利用产物中氘原子的数量来区分代谢产生的醇与还原产生的醇。
