Isolation and Characterization of Two Major Urinary Metabolites of Δ ¹ -Tetrahydrocannabinol

Abstract

Two of the major metabolites which appear in rabbit urine after the administration of Delta(1)-tetrahydrocannabinol have been isolated and their structures have been tentatively established. The available evidence indicates that they are 7-carboxy-Delta(1)-tetrahydrocannabinols with an additional hydroxyl group on the side chain. The substances occur both free and as conjugates.

Human Cannabinoid Pharmacokinetics

“…Hepatic Metabolism-Burstein and co-workers were the first to show that 11-OH-THC and THC-COOH are primary metabolites of THC in rabbits and rhesus monkeys [85][86][87]. They also documented that THC can be metabolized in the brain.…”

Studies of cannabinoid metabolites — a free radical immunoassay

“…Metabolic oxidation of the 7-methyl function to a carboxyl group, leading to analogs of III, is known [10]. the same urines spiked with 0.7 tag/ml of the acid derivative III.…”

The concept of regioselectivity in drug metabolism

“…On the other hand, metabolism of A 9 -~~c by the same route has recently been shown to produce the 3' -hydroxy and 4'-hydroxy derivatives using dog lung and liver; these derivatives were generated as major metabolites from the lung, but as minor metabolites from the liver (Widman, Nordqvist & others, 1975). In the rabbit two major urinary metabolites of were the 1'-hydroxy and 2'-hydroxy derivatives of As-THC-1 1-oic acid (XI) (Burstein, Rosenfeld & Wittstruck, 1972). These findings are important in the light of the reported pharmacological activity of 2' -, 3' -and 5'-hydroxy-A8THC, and of the lack of activity of 1'-hydroxy-A*-THC (Widman & others, 1975).…”