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Molecules 2015, 20(4), 5329-5345; doi:10.3390/molecules20045329

Economical Synthesis of 13C-Labeled Opiates, Cocaine Derivatives and Selected Urinary Metabolites by Derivatization of the Natural Products

1
Department of Chemistry, Norwegian University of Science and Technology, Høgskoleringen 5, Trondheim NO-7491, Norway
2
Chiron AS, Stiklestadveien 1, Trondheim 7041, Norway
*
Author to whom correspondence should be addressed.
Academic Editor: Isabel C. F. R. Ferreira
Received: 10 November 2014 / Revised: 10 February 2015 / Accepted: 19 March 2015 / Published: 25 March 2015
(This article belongs to the Collection Bioactive Compounds)
View Full-Text   |   Download PDF [571 KB, uploaded 25 March 2015]   |  

Abstract

The illegal use of opiates and cocaine is a challenge world-wide, but some derivatives are also valuable pharmaceuticals. Reference samples of the active ingredients and their metabolites are needed both for controlling administration in the clinic and to detect drugs of abuse. Especially, 13C-labeled compounds are useful for identification and quantification purposes by mass spectroscopic techniques, potentially increasing accuracy by minimizing ion alteration/suppression effects. Thus, the synthesis of [acetyl-13C4]heroin, [acetyl-13C4-methyl-13C]heroin, [acetyl-13C2-methyl-13C]6-acetylmorphine, [N-methyl-13C-O-metyl-13C]codeine and phenyl-13C6-labeled derivatives of cocaine, benzoylecgonine, norcocaine and cocaethylene was undertaken to provide such reference materials. The synthetic work has focused on identifying 13C atom-efficient routes towards these derivatives. Therefore, the 13C-labeled opiates and cocaine derivatives were made from the corresponding natural products. View Full-Text
Keywords: 13C-labeled standards; heroin; codeine; morphine; 6-acetylmorphine; cocaine; benzoylecgonine; norcocaine; cocaethylene 13C-labeled standards; heroin; codeine; morphine; 6-acetylmorphine; cocaine; benzoylecgonine; norcocaine; cocaethylene
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Karlsen, M.; Liu, H.; Johansen, J.E.; Hoff, B.H. Economical Synthesis of 13C-Labeled Opiates, Cocaine Derivatives and Selected Urinary Metabolites by Derivatization of the Natural Products. Molecules 2015, 20, 5329-5345.

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