MDMB-CHMICA is an

indole Indole is an aromatic heterocyclic organic compound with the formula C8 H7 N. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered pyrrole ring. Indole is widely distributed in the natural environme ...

-based

synthetic cannabinoid Synthetic cannabinoids are a class of designer drug molecules that bind to the same receptors to which cannabinoids ( THC, CBD and many others) in cannabis plants attach. These novel psychoactive substances should not be confused with synth ...

that is a potent

agonist An agonist is a chemical that activates a receptor to produce a biological response. Receptors are cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an antagonist blocks the action of the ago ...

of the CB₁ receptor and has been sold online as a

designer drug A designer drug is a structural or functional analog of a controlled substance that has been designed to mimic the pharmacological effects of the original drug, while avoiding classification as illegal and/or detection in standard drug tests. Des ...

. 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 of MDMB-CHMINACA) has been identified on the designer drug market in 2015 as AMB-CHMINACA.

Chemistry

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. An (S)-configuration for the ''tert''-leucinate group is unsurprising since MDMB-CHMICA is likely synthesized from the abundant and inexpensive "L" form of the appropriate ''tert''-leucinate reactant.

Pharmacology

MDMB-CHMICA acts as a highly potent full

of the CB₁ receptor with an efficacy of 94% and an EC₅₀ value of 0.14 nM, which is approximately 8 times lower than the EC₅₀ of

JWH-018 JWH-018 (1-pentyl-3-(1-naphthoyl)indole, NA-PIMO or AM-678) is an analgesic chemical from the naphthoylindole family that acts as a full agonist at both the CB1 and CB2 cannabinoid receptors, with some selectivity for CB2. It produces effects in a ...

(1.13 nM) and twofold lower than

AB-CHMINACA AB-CHMINACA is an indazole-based synthetic cannabinoid. It is a potent agonist of the CB1 receptor (''K''i = 0.78 nM) and CB2 receptor (''K''i = 0.45 nM) and fully substitutes for Δ9-THC in rat discrimination st ...

(0.27 nM).

Metabolism

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.

Side effects

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. Side effects such as unconsciousness or coma, hyperemesis, nausea, seizures, convulsions, tachycardia,

bradycardia Bradycardia (also sinus bradycardia) is a slow resting heart rate, commonly under 60 beats per minute (BPM) as determined by an electrocardiogram. It is considered to be a normal heart rate during sleep, in young and healthy or elderly adults, ...

, 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.

Legal status

In the United States, MDMB-CHMICA is a

Schedule I controlled substance This is the list of Schedule I drugs as defined by the United States Controlled Substances Act.21 CFRbr>1308.11(CSA Sched I) with changes through (Oct 18, 2012). Retrieved September 6, 2013. The following findings are required for drugs to be pla ...

. MDMB-CHMICA is illegal in Austria, Canada, China, Croatia, Denmark, Estonia, Finland, Germany, Greece, Hungary, Latvia, Lithuania, Louisiana, Luxembourg, Norway, Portugal, Turkey, the UK, Sweden and Switzerland. In August 2016 the

European Commission The European Commission (EC) is the executive of the European Union (EU). It operates as a cabinet government, with 27 members of the Commission (informally known as "Commissioners") headed by a President. It includes an administrative body ...

proposed a ban on MDMB-CHMICA across the

European Union The European Union (EU) is a supranational political and economic union of member states that are located primarily in Europe. The union has a total area of and an estimated total population of about 447million. The EU has often been ...

. In 27 February 2017 the Commission adopted an implementing act in banning MDMB-CHMICA, and

Member States A member state is a state that is a member of an international organization or of a federation or confederation. Since the World Trade Organization (WTO) and the International Monetary Fund (IMF) include some members that are not sovereign states ...

shall take the necessary measures to subject it to control measures and criminal penalties no later than by 4 March 2018.

Seizures

Over 3600 MDMB-CHMICA seizures between 2014 and 2016 in 19 member states of the European Union have been reported to the

European Monitoring Centre for Drugs and Drug Addiction The European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) is an agency of the European Union located in Lisbon, Portugal, and established in 1993. In June 2022, the Council of the European Union approved a reform of the organization ...

(EMCDDA), including a 40 kg seizure icin Luxembourg in December 2014.

References

{{Cannabinoidergics Indoles Cannabinoids Designer drugs Indolecarboxamides