Absolute configuration of the synthetic cannabinoid MDMB-CHMICA with its chemical characteristics in illegal products

  title={Absolute configuration of the synthetic cannabinoid MDMB-CHMICA with its chemical characteristics in illegal products},
  author={Lars Andernach and Stefan Pusch and Carina Weber and Dieter Schollmeyer and Sascha M{\"u}nster-M{\"u}ller and Michael P{\"u}tz and Till Opatz},
  journal={Forensic Toxicology},
A seized sample of the synthetic cannabinoid MDMB-CHMICA was studied by means of vibrational and electronic circular dichroism spectroscopy and found to have (S)-configuration by comparison of the experimental spectra with density functional theory calculations. We were able to additionally confirm the absolute configuration was additionally confirmed using X-ray crystallography. Furthermore, the title compound was extracted from five commercially available “Spice-like” herbal mixtures. The… 
Characterization of the synthetic cannabinoid MDMB-CHMCZCA
The synthetic cannabinoid MDMB-CHMCZCA was characterized by various spectroscopic techniques including NMR spectroscopy and tandem mass spectrometry and the enantiomeric purity of samples from test purchases and police seizures was assessed by a self-developed chiral HPLC method.
Chemical profiling of the synthetic cannabinoid MDMB-CHMICA: Identification, assessment, and stability study of synthesis-related impurities in seized and synthesized samples.
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-carboxylic acid)-3,3-dimethylbutanoate) were characterized and provided first insights into the manufacturing process and the precursor compounds used.
In Silico Infrared Characterization of Synthetic Cannabinoids by Quantum Chemistry and Chemometrics
In silico methods are an alternative that provides information about the spectra of undetected substances that can help to identify new drugs, to increase knowledge about them, and to feed information procedures.
Synthetic cannabinoid receptor agonists and their human metabolites in sewage water: Stability assessment and identification of transformation products.
The majority of investigated SCRAs, excluding the selected human metabolites, was recalcitrant to microbial degradation in sewage systems over a period of 29 days, and among the ten newly identified TPs three could be considered as relevant markers and should be included into future WBE studies to gain further insight into use and prevalence ofSCRAs on the drug market.
Enantiospecific Synthesis, Chiral Separation, and Biological Activity of Four Indazole-3-Carboxamide-Type Synthetic Cannabinoid Receptor Agonists and Their Detection in Seized Drug Samples
A method to compare potency between samples containing different SCRAs at varying concentrations was developed and applied in this small preliminary study and provides a simplified method for assessing and communicating the risk of their use.
The ongoing challenge of novel psychoactive drugs of abuse. Part I. Synthetic cannabinoids (IUPAC Technical Report)
Abstract In the past decade, the world has experienced a large increase in the number of novel compounds appearing on the illicit drug market for recreational purposes. Such substances are designed
Shape Matters: The Application of Activity-Based In Vitro Bioassays and Chiral Profiling to the Pharmacological Evaluation of Synthetic Cannabinoid Receptor Agonists in Drug-Infused Papers Seized in Prisons.
The importance of SCRA-CB1 receptor interactions in the 'head' or 'linked group' moiety is demonstrated, with the conformation of the 'bulky' tert-leucinate group greatly affecting potency, significantly greater than the difference observed between valinate SCRA enantiomers.
The Chemistry and Pharmacology of Synthetic Cannabinoid Receptor Agonist New Psychoactive Substances: Evolution.
This chapter will chart the evolution of recently identified SCRA NPS chemotypes, as well as their putative manufacturing by-products and thermolytic degradants, and describe structure-activity relationships within each class.
Evaluation of carboxamide-type synthetic cannabinoids as CB1/CB2 receptor agonists: difference between the enantiomers
This is the first report to show that the (R)-enantiomers of the carboxamide-type synthetic cannabinoids have the potency to activate CB1 and CB2 receptors.


Identification and analytical characteristics of synthetic cannabinoids with an indazole-3-carboxamide structure bearing a N-1-methoxycarbonylalkyl group
The peculiarities of mass-spectral fragmentation of the compounds after electron ionization (EI) ionization and collision-induced dissociation (CID) were studied and will enable their identification in a variety of materials seized from criminals.
Identification and quantification of synthetic cannabinoids in “spice-like” herbal mixtures: update of the German situation for the spring of 2015
In February 2015, 13 “spice-like” products, available on the German market, were analyzed. In total, eight different synthetic cannabinoids were identified by gas chromatography–mass spectrometry
Identification of a cannabinoid analog as a new type of designer drug in a herbal product.
A new type of designer drug, a cannabinoid analog (1), was found in a herbal product distributed on the illegal drug market in Japan in expectation of its narcotic effect. The structure of 1 was
Acute toxicity due to the confirmed consumption of synthetic cannabinoids: clinical and laboratory findings.
Acute toxic symptoms associated with their use are also reported after intake of high doses of cannabis, but agitation, seizures, hypertension, emesis and hypokalaemia seem to be characteristic to the synthetic cannabinoids, which are high-affinity and high-efficacy agonists of the CB(1) receptor.
Determination of methamphetamine enantiomer ratios in urine by gas chromatography-mass spectrometry.
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This work presents the extension of a series of 6aS-trans cannabinoids with novel derivatives, including water soluble derivatives and congeners of dexanabinol, which demonstrated significant neuroprotective properties which prompted its development as a therapeutic agent.
Reply to 'Sudden Cardiac Death Following Use of the Synthetic Cannabinoid MDMB-CHMICA'.
Some more data is added on MDMB-CHMICA serum concentrations encountered in forensic case work because of the high prevalence and the limited data published in the literature so far.
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To avoid a cat-and-mouse game between regulators and illicit drug manufacturers, a comprehensive system (generic scheduling) for designating naphthoylindole-type synthetic cannabinoids, with particular substituents, was introduced into the Designated Substances in 2013.
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This article outlines theory and practice of the comparison of calculated and experimental electronic circular dichroism (ECD) curves to determine the absolute configuration of chiral molecules and introduces a similarity factor, which helps to quantify the degree of matching of curves.