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Münster-Müller, S.* ; Hansen, S.* ; Opatz, T.* ; Zimmermann, R. ; Pütz, M.*

Chemical profiling of the synthetic cannabinoid MDMB-CHMICA: Identification, assessment, and stability study of synthesis-related impurities in seized and synthesized samples.

Drug Test. Anal. 11, 1192-1206 (2019)
Postprint DOI PMC
Open Access Green
In this work, the most discriminating synthesis-related impurities found in samples from seizures and controlled synthesis of the synthetic cannabinoid MDMB-CHMICA (methyl (S)-2-(1-(cyclohexylmethyl)-1H-indole-3-carboxamido)-3,3-dimethylbutanoate) were characterized. Based on 61 available powder samples of MDMB-CHMICA, 15 key-impurities were assessed, isolated in larger quantities via flash chromatography and structurally elucidated and characterized via high resolution mass spectrometry and nuclear magnetic resonance spectroscopy. Apart from verifying the relation of the impurities to the major component, the interpretation of their chemical structures with distinct structural elements provided first insights into the manufacturing process and the precursor compounds used. Following liquid chromatography mass spectrometry analysis of the 15 key-impurities, the 61 seized samples of MDMB-CHMICA were evaluated and classified via multivariate data analysis based on the corresponding relative peak areas. In a second part of this work, stability tests and multiple controlled syntheses of MDMB-CHMICA were carried out to better understand variations in impurity signatures and to assess the significance of variations in the impurity patterns of seized samples. The last coupling step of the amino acid with 1-(cyclohexylmethyl)-1H-indole-3-carboxylic acid was performed using the coupling agents oxalyl chloride, thionyl chloride, and HATU. Furthermore, the impact of reaction time and temperature on the impurity profile were investigated. Overall, eight new impurities were found in the controlled syntheses and two degradation products of MDMB-CHIMCA were found in the course of the stability tests. Replicates of a synthesis conducted on the same day showed similar impurity signatures; on different days they showed discriminable signatures. The use of different coupling reagents or conditions gave clearly distinguishable impurity signatures.
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Publikationstyp Artikel: Journalartikel
Dokumenttyp Wissenschaftlicher Artikel
Schlagwörter Controlled Synthesis ; Impurity Profiling ; Lc-ms ; Mdmb-chmica ; New Psychoactive Substances (nps); Reductive Amination; Harmonized Method; Amphetamine; Route; Methylamphetamine; Formylkynurenine; Pharmacology; Derivatives; Tryptophan; Fubinaca
Sprache englisch
Veröffentlichungsjahr 2019
HGF-Berichtsjahr 2019
ISSN (print) / ISBN 1942-7603
e-ISSN 1942-7611
Zeitschrift Drug testing and analysis
Quellenangaben Band: 11, Heft: 8, Seiten: 1192-1206 Artikelnummer: , Supplement: ,
Verlag Wiley
Verlagsort Chichester
Begutachtungsstatus Peer reviewed
Institut(e) Cooperation Group Comprehensive Molecular Analytics (CMA)
POF Topic(s) 30202 - Environmental Health
Forschungsfeld(er) Environmental Sciences
PSP-Element(e) G-504500-001
DOI 10.1002/dta.2652
WOS ID WOS:000478888800007
Scopus ID 85067480099
PubMed ID 31124282
Erfassungsdatum 2019-05-29
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