137530-65-5Relevant academic research and scientific papers
Synthesis of [2H6]-labelled metabolites of cannabinoids
Feng, Shixia,ElSohly, Mahmoud A.
, p. 655 - 662 (2000)
Four [2H6]-labelled metabolites of cannabinoids were synthesized for use as internal standards for GC/MS analysis. The hexadeutero-ketone 3, prepared from ketal 1, undergoes a Shapiro reaction to give (±)-6,6-[2H6]dimethyl-11-nor-9-carboxy-Δ9-THC (4a) as the major product. The minor product, (±)-6,6-[2H6]dimethyl-11-nor-9-carboxy-Δ8-THC (4b), was obtained after hydrolysis of its acetate methyl ester which was isolated using preparative HPLC. Reduction of 4a gave (±)-6,6-[2H6]dimethyl-11-hydroxy-Δ9-THC (6). (±)-6,6-[2H6]dimethyl-8β,11-dihydroxy-Δ9-THC (10), was also prepared from 3 using a reported procedure for the non-labelled analog.
