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Synthesis of N ‐methyl‐trideuterium‐labelled m ‐hydroxybenzoylecgonine as an internal standard for GC/MS analysis
Author(s) -
Feng Shixia,
ElSohly Mahmoud A.
Publication year - 1999
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/(sici)1099-1344(199911)42:11<1031::aid-jlcr258>3.0.co;2-c
Subject(s) - chemistry , demethylation , hydrolysis , acylation , moiety , metabolite , chromatography , organic chemistry , biochemistry , gene expression , dna methylation , gene , catalysis
m ‐Hydroxybenzoylecgonine is an important metabolite of cocaine. A synthesis of [8‐C 2 H 3 ]‐ m ‐hydroxybenzoylecgonine ( 7 ) for use as an internal standard in GC/MS analysis of m ‐hydroxybenzoylecgonine, is described. N ‐Demethylation of cocaine ( 1 ) gave norcocaine ( 2 ) which was converted to [8‐C 2 H 3 ]cocaine ( 3 ) upon treatment with CD 3 I. Hydrolysis of 3 followed by esterification gave [8‐C 2 H 3 ]ecgonine methyl ester ( 5 ). [8‐C 2 H 3 ]‐ m ‐Hydroxycocaine ( 6 ) was obtained from 5 by first acylation and then selective hydrolysis of the protected m ‐hydroxy moiety under acidic conditions. The title compound, 7 , was obtained by selective hydrolysis of 6 in refluxing water. Copyright © 1999 John Wiley & Sons, Ltd.