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| Formula | C23H32N2O3 |
| Molar mass | 384.520 g·mol−1 |
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MDMB-CHMICA[3] is anindole-basedsynthetic cannabinoid that is a potentagonist of theCB1 receptor and has been sold online as adesigner drug.[2][4][5][6] While MDMB-CHMICA was initially sold under the name "MMB-CHMINACA", the compound corresponding to this code name (i.e. the isopropyl instead of t-butyl analogue ofMDMB-CHMINACA) has been identified on the designer drug market in 2015 asAMB-CHMINACA.[7]
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]
In the United States, MDMB-CHMICA is aSchedule I controlled substance.[23]
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]
