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

Karlsen, Morten; Liu, Huiling; Johansen, Jon Eigill; Hoff, Bård Helge
Journal article, Peer reviewed
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molecules-20-05329.pdf (570.8Kb)
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http://hdl.handle.net/11250/2359594
Utgivelsesdato
2015
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  • Publikasjoner fra CRIStin - NTNU [26604]
Originalversjon
Molecules 2015, 20(4):5329-5345   10.3390/molecules20045329
Sammendrag
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-Ometyl-

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.
Utgiver
MDPI
Tidsskrift
Molecules

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