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MAB-CHMINACA is a research chemical though it was created in 2009 by Pfizer as an analgesic which is synonymous to painkiller medications. In early 2015 it was identified in cannabinoid blends.

Chemistry of MAB-CHMINACA

The chemical formula of MAB-CHMINACA is “N-[(2S)-1-amino-3, 3-dimethyl-1-oxobutan-2-yl]-1-(cyclohexylmethyl) indazole-3-carboxamide”. 

The molecular weight of this drug has been calculated to be 370.24 g/mol and the purity of this substance in its purest forms has been calculated to be approximately equal to or greater than 98%.

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N-(1-amino-3,3-dimethyl-1-oxobutan-2-yl)-1-

(cyclohexylmethyl)-1H-indazole-3-carboxamide carboxamide

is commonly referred to as ADB-CHMINACA or MAB-

CHMINACA

ADB-CHMINACA is a synthetic cannabinoid receptor agonist.

It has an indazole core, which is a common structural feature

in many of the synthetic cannabinoids monitored by the

EMCDDA.

Two synthetic cannabinoid receptor agonists have been

recently controlled under Schedule II of the United Nations

Convention on Psychotropic Substances of 1971: JWH-018 

and AM-2201 . In addition, MDMB-CHMICA, 5F-APINACA

(5F-AKB48) and XLR-11 will be included in the same schedule.

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ADB-CHMINACA (also known as MAB-CHMINACA) is an indazole-based synthetic cannabinoid. It is a potent agonist of the CB1 receptor with a binding affinity of Ki = 0.289 nM and was originally developed by Pfizer in 2009 as an analgesic medication. It was identified in cannabinoid blends in Japan in early 2015.

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Ten ADB-CHMINACA major metabolites were identified in several incubations with cryopreserved human hepatocytes. Most transformations occurred at the cyclohexylmethyl tail of the compound.

The chemical formula of MAB-CHMINACA is “N-[(2S)-1-amino-3, 3-dimethyl-1-oxobutan-2-yl]-1-(cyclohexylmethyl) indazole-3-carboxamide”. The molecular weight of this drug has been calculated to be 370.24 g/mol and the purity of this substance in its purest forms has been calculated to be approximately equal to or greater than 98%. The molecular formula for MAB-

CHMINACA is C 21 H 30 N 4 O 2 and it is a neat solid substance and it is usually the form in which it is commercially sold. MAB-CHMINACA comes in three major metabolites which are M7, M10 and M11. The recommended storage temperature for the drug is 20°C while the stability of the molecule of this drug is known to be equal to or greater than two years.

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What is MAB-CHMINACA used for?

The drug is extensively used as pain killer or an analgesic substance which was the purpose it was initially produced. It acts on the peripheral and central nervous system in order to cause mitigation in pain caused due to any reason. It is usually used as a sedative for muscle pain by people who are suffering with long term illnesses or temporary illnesses which cause long term pain in muscles.

 It may also be used for stress reduction and memory relocation. It causes psychological impact of well being in people and is known to enhance the creative capabilities of people. It has also been used by people for recreational purposes.

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It has wide ranging applications and has been used by both researchers and common people. It is primarily listed as a research chemical and intended to be used for forensic applications. It is also intended to be used as an analytical reference standard.

AB-CHMINACA (Item No. 15434) is an indazole-based synthetic cannabinoid (CB) that is structurally related to AB-FUBINACA (Item Nos. ISO60211 | ISO00134 | 14039), a high affinity ligand of the CB1 receptor (Ki = 0.9 nM).1,2 MAB-CHMINACA is structurally similar to AB-CHMINACA by bearing an identical cyclohexyl group; however, the isobutyl moiety is substituted with a tert-butyl group. It is a potent agonist of the CB1 receptor with a reported Ki value of 0.289 nM.2 This product is intended for forensic and research applications.

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WARNING This product is not for human or veterinary use.

During the latter part of 2014, we experienced an autopsy case in which 5-fluoro-ADB, one of the most dangerous synthetic cannabinoids, was identified and quantitated in solid tissues and in three herbal blend products [Forensic Toxicol (2015). 

At that time, although we suspected that there may be some drug(s) other than 5-fluoro-ADB in the herbal products, all trials to find it/them were unsuccessful. Subsequently, we carefully re-examined the presence of other synthetic cannabinoid(s) in the above herbal blend products using accurate mass spectrometry and found two new compounds, 5-fluoro-ADB-PINACA and MAB-CHMINACA.

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In the present communication, we report the distribution of MAB-CHMINACA in body fluids and solid tissue specimens collected from the same deceased individual (kept frozen at -80 °C) as described above for demonstration of 5-fluoro-ADB. Unexpectedly, unchanged MAB-CHMINACA could be identified and quantified in whole blood and in pericardial fluid specimens, but it was below the detection limit (0.1 ng/ml) in the urine specimen. 

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A higher concentration of MAB-CHMINACA could be found in all of the nine solid tissues; the highest concentration of MAB-CHMINACA was found in the liver (156 ng/g), followed by the kidney, pancreas and so on. The compounds were detected in all nine solid tissues; their levels were generally higher than those in the whole blood and pericardial fluid. Contrary to expectations, the concentration of MAB-CHMINACA in the adipose tissue was relatively low. 

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Our results show that the victim smoked one of the three herbal blend products containing both MAB-CHMINACA and 5-fluoro-ADB, resulting in the coexistence of both compounds. It should be concluded that 5-fluoro-ADB and MAB-CHMINACA synergically exerted their toxicities, leading to death after a short interval. 

The differences in the distribution of 5-fluoro-ADB and MAB-CHMINACA among the cadaver specimens were also discussed in view of the structures of both compounds. To our knowledge, this is the first report to demonstrate MAB-CHMINACA in biological/human specimens.

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ADB-CHMINACA (MAB-CHMINACA) is a new synthetic cannabinoid with high potency and many reported adverse events and fatalities. The drug is currently scheduled in several countries in Europe and the USA. Analytical methods need to be developed to confirm ADB-CHMINACA intake for clinical and forensic programs. For many synthetic cannabinoids, the parent compound is not detectable in biological samples after intake, making the detection of metabolites the only way to prove consumption. Therefore, detection of ADB-CHMINACA metabolites in biological specimens is critical. Since there are currently no published data on ADB-CHMINACA metabolism, we aimed to identify its major metabolites. 

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Cryopreserved human hepatocytes were incubated with 10 μmol/L ADB-CHMINACA for 3 h. Incubations were analyzed with liquid chromatography on a biphenyl column, high resolution tandem mass spectrometry (orbitrap), and metabolite identification software. 

A reference standard of six commercially available potential metabolites was simultaneously analyzed under the same conditions to allow correct assignment of isomers. We detected ten major metabolites. Biotransformations mainly occurred at the cyclohexylmethyl tail of the compound, as also observed with structural analogs' metabolism. 

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Minor reactions also occurred at the tert-butyl chain. Only two analytical standards of potential metabolites matched an actual metabolite detected in hepatocyte incubations. We recommend A9 (ADB-CHMINACA hydroxycyclohexylmethyl), A4 (ADB-CHMINACA 4″-hydroxycyclohexyl), and A6 (ADB-CHMINACA hydroxycyclohexylmethyl) as metabolite targets to document ADB-CHMINACA intake in clinical and forensic cases. Additionally, these results will guide analytical standard manufacturers to better provide suitable references for further studies on ADB-CHMINACA metabolism.

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