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Synthesis of [ 2 H 6 ]‐labelled metabolites of cannabinoids
Author(s) -
Feng Shixia,
Elsohly Mahmoud A.
Publication year - 2000
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/1099-1344(200006)43:7<655::aid-jlcr350>3.0.co;2-t
Subject(s) - chemistry , ketone , hydrolysis , labelling , high performance liquid chromatography , chromatography , organic chemistry , biochemistry
Four [ 2 H 6 ]‐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‐[ 2 H 6 ]dimethyl‐11‐nor‐9‐carboxy‐Δ 9 ‐THC ( 4a ) as the major product. The minor product, (±)‐6,6‐[ 2 H 6 ]dimethyl‐11‐nor‐9‐carboxy‐Δ 8 ‐THC ( 4b ), was obtained after hydrolysis of its acetate methyl ester which was isolated using preparative HPLC. Reduction of 4a gave (±)‐6,6‐[ 2 H 6 ]dimethyl‐11‐hydroxy‐Δ 9 ‐THC ( 6 ). (±)‐6,6‐[ 2 H 6 ]dimethyl‐8β,11‐dihydroxy‐Δ 9 ‐THC ( 10 ), was also prepared from 3 using a reported procedure for the non‐labelling analog. Copyright © 2000 John Wiley & Sons, Ltd.