MDMB-CHMICA is an

indole Indole is an aromatic heterocyclic organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other c ...

-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 synthe ...

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 ag ...

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. D ...

. 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 MDMB-CHMINACA (also known as MDMB(N)-CHM) is an indazole-based synthetic cannabinoid that acts as a potent agonist of the CB1 receptor, and has been sold online as a designer drug. It was invented by Pfizer in 2008, and is one of the most potent ...

) 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 Efficacy is the ability to perform a task to a satisfactory or expected degree. The word comes from the same roots as ''effectiveness'', and it has often been used synonymously, although in pharmacology a distinction is now often made between ...

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 ...

(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 union, supranational political union, political and economic union of Member state of the European Union, member states that are located primarily in Europe, Europe. The union has a total area of ...

. In 27 February 2017 the Commission adopted an

implementing act Primary legislation and secondary legislation (the latter also called delegated legislation or subordinate legislation) are two forms of law, created respectively by the legislative and executive branches of governments in representative democ ...

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 s ...

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