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

Publikationstyp:
Zeitschriftenaufsatz
Metadaten:
Autoren
  • Sascha Muenster-Mueller
  • Steven Hansen
  • Till Opatz
  • Ralf Zimmermann
  • Michael Puetz
Autoren-URL
https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000478888800007&DestLinkType=FullRecord&DestApp=WOS_CPL
DOI
10.1002/dta.2652
eISSN
1942-7611
Externe Identifier
  • Clarivate Analytics Document Solution ID: IN7VB
  • PubMed Identifier: 31124282
ISSN
1942-7603
Ausgabe der Veröffentlichung
8
Zeitschrift
DRUG TESTING AND ANALYSIS
Schlüsselwörter
  • controlled synthesis
  • impurity profiling
  • LC-MS
  • MDMB-CHMICA
  • new psychoactive substances (NPS)
Paginierung
1192 - 1206
Datum der Veröffentlichung
2019
Status
Published
Titel
Chemical profiling of the synthetic cannabinoid MDMB-CHMICA: Identification, assessment, and stability study of synthesis-related impurities in seized and synthesized samples
Sub types
  • Article
Ausgabe der Zeitschrift
11

Datenquelle: Web of Science (Lite)

Andere Metadatenquellen:
Abstract
<jats:title>Abstract</jats:title><jats:p>In this work, the most discriminating synthesis‐related impurities found in samples from seizures and controlled synthesis of the synthetic cannabinoid MDMB‐CHMICA (methyl (<jats:italic>S</jats:italic>)‐2‐(1‐(cyclohexylmethyl)‐1<jats:italic>H</jats:italic>‐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)‐1<jats:italic>H</jats:italic>‐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.</jats:p>
Autoren
  • Sascha Münster‐Müller
  • Steven Hansen
  • Till Opatz
  • Ralf Zimmermann
  • Michael Pütz
DOI
10.1002/dta.2652
eISSN
1942-7611
ISSN
1942-7603
Ausgabe der Veröffentlichung
8
Zeitschrift
Drug Testing and Analysis
Sprache
en
Online publication date
2019
Paginierung
1192 - 1206
Datum der Veröffentlichung
2019
Status
Published
Herausgeber
Wiley
Herausgeber URL
http://dx.doi.org/10.1002/dta.2652
Datum der Datenerfassung
2023
Titel
Chemical profiling of the synthetic cannabinoid MDMB‐CHMICA: Identification, assessment, and stability study of synthesis‐related impurities in seized and synthesized samples
Ausgabe der Zeitschrift
11

Datenquelle: Crossref

Abstract
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.
Addresses
  • Federal Criminal Police Office, Forensic Science Institute, Wiesbaden, Germany.
Autoren
  • Sascha Münster-Müller
  • Steven Hansen
  • Till Opatz
  • Ralf Zimmermann
  • Michael Pütz
DOI
10.1002/dta.2652
eISSN
1942-7611
Externe Identifier
  • PubMed Identifier: 31124282
Funding acknowledgements
  • Directorate-General for Justice: JUST/2013/ISEC/DRUGS/AG/ISEC/4000006421
Open access
false
ISSN
1942-7603
Ausgabe der Veröffentlichung
8
Zeitschrift
Drug testing and analysis
Schlüsselwörter
  • Cannabinoids
  • Indoles
  • Chromatography, High Pressure Liquid
  • Drug Stability
  • Drug Contamination
  • Tandem Mass Spectrometry
  • Drug Trafficking
  • Illicit Drugs
Sprache
eng
Medium
Print-Electronic
Online publication date
2019
Paginierung
1192 - 1206
Datum der Veröffentlichung
2019
Status
Published
Datum der Datenerfassung
2019
Titel
Chemical profiling of the synthetic cannabinoid MDMB-CHMICA: Identification, assessment, and stability study of synthesis-related impurities in seized and synthesized samples.
Sub types
  • Journal Article
Ausgabe der Zeitschrift
11

Datenquelle: Europe PubMed Central

Abstract
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.
Date of acceptance
2019
Autoren
  • Sascha Münster-Müller
  • Steven Hansen
  • Till Opatz
  • Ralf Zimmermann
  • Michael Pütz
Autoren-URL
https://www.ncbi.nlm.nih.gov/pubmed/31124282
DOI
10.1002/dta.2652
eISSN
1942-7611
Funding acknowledgements
  • Directorate-General for Justice: JUST/2013/ISEC/DRUGS/AG/ISEC/4000006421
Ausgabe der Veröffentlichung
8
Zeitschrift
Drug Test Anal
Schlüsselwörter
  • LC-MS
  • MDMB-CHMICA
  • controlled synthesis
  • impurity profiling
  • new psychoactive substances (NPS)
  • Cannabinoids
  • Chromatography, High Pressure Liquid
  • Drug Contamination
  • Drug Stability
  • Drug Trafficking
  • Illicit Drugs
  • Indoles
  • Tandem Mass Spectrometry
Sprache
eng
Country
England
Paginierung
1192 - 1206
Datum der Veröffentlichung
2019
Status
Published
Datum, an dem der Datensatz öffentlich gemacht wurde
2020
Titel
Chemical profiling of the synthetic cannabinoid MDMB-CHMICA: Identification, assessment, and stability study of synthesis-related impurities in seized and synthesized samples.
Sub types
  • Journal Article
Ausgabe der Zeitschrift
11

Datenquelle: PubMed

Beziehungen:
Eigentum von

Werkzeuge