title: Economical synthesis of 13C-labeled opiates, cocaine derivatives and selected urinary metabolites by derivatization of the natural products.
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, (13)C-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-(13)C4]heroin, [acetyl-(13)C4-methyl-(13)C]heroin, [acetyl-(13)C2-methyl-(13)C]6-acetylmorphine, [N-methyl-(13)C-O-metyl-(13)C]codeine and phenyl-(13)C6-labeled derivatives of cocaine, benzoylecgonine, norcocaine and cocaethylene was undertaken to provide such reference materials. The synthetic work has focused on identifying (13)C atom-efficient routes towards these derivatives. Therefore, the (13)C-labeled opiates and cocaine derivatives were made from the corresponding natural products.
authors: Department of Chemistry, Norwegian University of Science and Technology, Høgskoleringen 5, Trondheim NO-7491, Norway. Morten.Karlsen@chiron.no.|Chiron AS, Stiklestadveien 1, Trondheim 7041, Norway. Morten.Karlsen@chiron.no.
authors: Morten
authors: M
authors: Karlsen
authors: Chiron AS, Stiklestadveien 1, Trondheim 7041, Norway. Huiling.Liu@chiron.no.
authors: Huiling
authors: H
authors: Liu
authors: Chiron AS, Stiklestadveien 1, Trondheim 7041, Norway. Jon.Johansen@chiron.no.
authors: Jon Eigill
authors: JE
authors: Johansen
authors: Department of Chemistry, Norwegian University of Science and Technology, Høgskoleringen 5, Trondheim NO-7491, Norway. bard.helge.hoff@chem.ntnu.no.
authors: Bård Helge
authors: BH
authors: Hoff
mesh_terms: D000701:Analgesics, Opioid / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000652:urine; D001688:Biological Products / Q000032:analysis* / Q000652:urine; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D003042:Cocaine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D003061:Codeine / Q000138:chemical synthesis / Q000737:chemistry; D003932:Heroin / Q000138:chemical synthesis / Q000737:chemistry; D006801:Humans; D015394:Molecular Structure; D009020:Morphine / Q000138:chemical synthesis* / Q000737:chemistry; D009022:Morphine Derivatives / Q000652:urine; D015813:Substance Abuse Detection / Q000592:standards; D016482:Urinalysis / Q000592:standards*
chemical_list: D000701:Analgesics, Opioid; D001688:Biological Products; D009022:Morphine Derivatives; C005618:benzoylecgonine; D003932:Heroin; D009020:Morphine; C066444:cocaethylene; D003042:Cocaine; D003061:Codeine