Several commercial samples of MDMB-CHMICA were found to exclusively contain the (S)-enantiomer based on vibrational and electronic circular dichroism spectroscopy and X-ray crystallography.[8] An (S)-configuration for thetert-leucinate group is unsurprising since MDMB-CHMICA is likely synthesized from the abundant and inexpensive "L" form of the appropriatetert-leucinate reactant.
MDMB-CHMICA acts as a highly potent fullagonist of theCB1 receptor with anefficacy of 94% and anEC50 value of 0.14 nM, which is approximately 8 times lower than the EC50 ofJWH-018 (1.13 nM) and twofold lower thanAB-CHMINACA (0.27 nM).[2][9][10]
MDMB-CHMICA's main metabolic reactions comprise mono-hydroxylations and hydrolysis of the carboxylic ester function. In total, 31 metabolites could be identified in vivo.[11][12][13]
Seventy-one serious adverse events, including 42 acute intoxications and 29 deaths (Germany (5), Hungary (3), Poland (1), Sweden (9), United Kingdom (10), Norway (1)) that occurred in nine European countries between 2014 and 2016 have been associated with MDMB-CHMICA.[2][14][15][16][17]
Side effects such as unconsciousness or coma, hyperemesis, nausea, seizures, convulsions, tachycardia,bradycardia, mydriasis, syncope, spontaneous urinating and defecating, shortness of breath, somnolence, respiratory acidosis, metabolic acidosis, collapse, lower limbs paralysis, chest pain, aggression and severe disturbance of behaviour were reported.[2][18][19][20][21][22]
MDMB-CHMICA is illegal in Austria, Canada, China,[24] Croatia, Denmark, Estonia, Finland, Germany, Greece, Hungary, Latvia, Lithuania, Louisiana,[25] Luxembourg, Norway, Portugal, Turkey, the UK, Sweden and Switzerland.[2]
In August 2016 theEuropean Commission proposed a ban on MDMB-CHMICA across theEuropean Union.[26]In 27 February 2017 the Commission adopted animplementing act in banning MDMB-CHMICA, andMember States shall take the necessary measures to subject it to control measures and criminal penalties no later than by 4 March 2018.[27]
Over 3600 MDMB-CHMICA seizures between 2014 and 2016 in 19 member states of the European Union have been reported to theEuropean Monitoring Centre for Drugs and Drug Addiction (EMCDDA),[2] including a 40 kg seizure [sic] in Luxembourg in December 2014.[28]
^Pulver B, Fischmann S, Gallegos A, Christie R (March 2023). "EMCDDA framework and practical guidance for naming synthetic cannabinoids".Drug Testing and Analysis.15 (3):255–276.doi:10.1002/dta.3403.PMID36346325.
^"MDMB-CHMICA". Southern Association of Forensic Scientists. Retrieved29 June 2015.
^Banister SD, Longworth M, Kevin R, Sachdev S, Santiago M, Stuart J, et al. (September 2016). "Pharmacology of Valinate and tert-Leucinate Synthetic Cannabinoids 5F-AMBICA, 5F-AMB, 5F-ADB, AMB-FUBINACA, MDMB-FUBINACA, MDMB-CHMICA, and Their Analogues".ACS Chemical Neuroscience.7 (9):1241–54.doi:10.1021/acschemneuro.6b00137.PMID27421060.
^Shevyrin V, Melkozerov V, Nevero A, Eltsov O, Shafran Y, Morzherin Y, et al. (August 2015). "Identification and analytical characteristics of synthetic cannabinoids with an indazole-3-carboxamide structure bearing a N-1-methoxycarbonylalkyl group".Analytical and Bioanalytical Chemistry.407 (21):6301–15.doi:10.1007/s00216-015-8612-7.PMID25893797.S2CID31838655.
^Andernach L, Pusch S, Weber C, Schollmeyer D, Münster-Müller S, Pütz M, et al. (1 June 2016). "Absolute configuration of the synthetic cannabinoid MDMB-CHMICA with its chemical characteristics in illegal products".Forensic Toxicology.34 (2):344–352.doi:10.1007/s11419-016-0321-1.S2CID20075407.
^Langer N, Lindigkeit R, Schiebel HM, Papke U, Ernst L, Beuerle T (January 2016). "Identification and quantification of synthetic cannabinoids in "spice-like" herbal mixtures: update of the German situation for the spring of 2015".Forensic Toxicology.34 (1):94–107.doi:10.1007/s11419-015-0292-7.S2CID24851329.
^Maeda H, Nagashima E, Hayashi YK, Kikura-Hanajiri R, Yoshida KI (2018). "MDMB-CHMICA induces thrashing behavior, bradycardia, and slow pressor response in a CB1- and CB2-receptor-dependent manner in conscious rats".Forensic Toxicology.36 (2):313–319.doi:10.1007/s11419-018-0405-1.ISSN1860-8965.S2CID46869442.
^Grigoryev A, Kavanagh P, Pechnikov A (July 2016). "Human urinary metabolite pattern of a new synthetic cannabimimetic, methyl 2-(1-(cyclohexylmethyl)-1H-indole-3-carboxamido)-3,3-dimethylbutanoate".Forensic Toxicology.34 (2):316–328.doi:10.1007/s11419-016-0319-8.S2CID20993024.
^Franz F, Angerer V, Moosmann B, Auwärter V (May 2017). "Phase I metabolism of the highly potent synthetic cannabinoid MDMB-CHMICA and detection in human urine samples".Drug Testing and Analysis.9 (5):744–753.doi:10.1002/dta.2049.PMID27504870.
^"关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived fromthe original on 1 October 2015. Retrieved1 October 2015.
