morphine is transformed into heroin by a.methylation b.acylation c.acetylation d.benzyolation
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Open AccessArticle
Economical Synthesis of 13C-Labeled Opiates, Cocaine Derivatives and Selected Urinary Metabolites by Derivatization of the Natural Products
by Morten Karlsen 1,2,Huiling Liu 2,Jon Eigill Johansen 2 andBård Helge Hoff 1,*
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
Molecules 2015, 20(4), 5329-5345;
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.
Keywords: 13C-labeled standards; heroin; codeine; morphine; 6-acetylmorphine; cocaine; benzoylecgonine; norcocaine; cocaethylene
1. Introduction
Drug abuse has a huge impact on individuals, their families, but also on society as a whole, due to loss of productivity, premature mortality, crime and healthcare costs [1]. However, narcotic drugs and psychotropic substances also have a variety of medical uses. Most importantly, opioids, such as codeine and morphine are indispensable for relieving moderate to severe pain [2,3]. Morphine is also used in the treatment of dyspnea [4,5], while codeine has been used for chronic cough [6] and diarrhea [7]. Heroin is a potent synthetic opiate analgesic synthesized from morphine by acetylation [8], but is banned for its high addictive character and finds little use in medicine. It is the most abused opiate and has become a worldwide rapidly increasing health problem. Some countries have started substitution therapy of heroin addicts, where the patient receives daily heroin doses under strict supervision [9].
In vivo, these drugs undergo metabolism to give a range of derivatives [10,11]. Thus, efficient analysis of both drugs and their metabolites in biological fluids are required in the fields of clinical toxicology and forensic toxicology, but also for workplace drug testing, testing of driving under the influence of drugs, doping analysis and rehabilitation programs. Moreover, in a therapy setting, there could be a need to track the use of such medicines and to confirm that the patients are using prescription medicines and not street material of varying quality. The most relevant opiate and cocaine derivatives
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