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Synthesis of [ 13 C 6 ]‐labelled phenethylamine derivatives for drug quantification in biological samples
Author(s) -
Karlsen Morten,
Liu HuiLing,
Berg Thomas,
Johansen Jon Eigill,
Hoff Bård Helge
Publication year - 2014
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/jlcr.3193
Subject(s) - phenethylamine , chemistry , designer drug , mass spectrometry , methylenedioxy , tandem mass spectrometry , chromatography , stereochemistry , organic chemistry , drug , pharmacology , medicine , alkyl , halogen
The availability of high‐quality 13 C‐labelled internal standards will improve accurate quantification of narcotics and drugs in biological samples. Thus, the synthesis of 10 [ 13 C 6 ]‐labelled phenethylamine derivatives, namely amphetamine, methamphetamine, 3,4‐methylenedioxyamphetamine, 3,4‐methylenedioxymethamphetamine, 3,4‐methylenedioxy‐ N ‐ethylamphetamine, 4‐methoxyamphetamine, 4‐methoxymethamphetamine, 3,5‐dimethoxyphenethylamine 4‐bromo‐2,5‐dimethoxyphenethylamine and 2,5‐dimethoxy‐4‐iodophenethylamine, have been undertaken. [ 13 C 6 ]‐Phenol proved to be an excellent starting material for making 13 C‐labelled narcotic substances in the phenethylamine class, and a developed Stille‐type coupling enabled an efficient synthesis of the 3,4‐methylenedioxy and 4‐methoxy derivatives. The pros and cons of alternative routes and transformations are also discussed. The [ 13 C 6 ]‐labelled compounds are intended for use as internal standards in forensic analysis, health sciences and metabolomics studies by gas chromatography‐mass spectrometry and liquid chromatography‐tandem mass spectrometry. Copyright © 2014 John Wiley & Sons, Ltd.