ADB-CHMINACA

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.[1][2] It was identified in cannabinoid blends in Japan in early 2015.[3]

ADB-CHMINACA
Legal status
Legal status
  • CA: Schedule II
  • DE: Anlage II (Authorized trade only, not prescriptible)
  • UK: Class B
  • US: Schedule I
  • Illegal in Singapore, Sweden, Switzerland
Identifiers
IUPAC name
  • N-[(2S)-1-Amino-3,3-dimethyl-1-oxobutan-2-yl]-1-(cyclohexylmethyl)indazole-3-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC21H30N4O2
Molar mass370.497 g·mol−1
3D model (JSmol)
SMILES
  • CC(C)(C)[C@H](NC(=O)c1nn(CC2CCCCC2)c3ccccc13)C(N)=O
InChI
  • InChI=1S/C21H30N4O2/c1-21(2,3)18(19(22)26)23-20(27)17-15-11-7-8-12-16(15)25(24-17)13-14-9-5-4-6-10-14/h7-8,11-12,14,18H,4-6,9-10,13H2,1-3H3,(H2,22,26)(H,23,27)/t18-/m1/s1
  • Key:ZWCCSIUBHCZKOY-GOSISDBHSA-N

Side effects

There have been a number of reported cases of deaths and hospitalizations in relation to this synthetic cannabinoid.[4][5][6][7][8][9][10][11]

In the United States, ADB-CHMINACA is a Schedule I controlled substance.[12] Prior to its listing at the federal level in 2018, Louisiana placed ADB-CHMINACA on its Schedule I list by emergency scheduling in 2014.[13]

Sweden's public health agency suggested to classify ADB-CHMINACA as hazardous substance on November 10, 2014.[14]

ADB-CHMINACA is listed in the Fifth Schedule of the Misuse of Drugs Act (MDA) and therefore illegal in Singapore as of May 2015.[15]

ADB-CHMINACA is illegal in Switzerland as of December 2015.[16]

Metabolism

Ten ADB-CHMINACA major metabolites were identified in several incubations with cryopreserved human hepatocytes. Most transformations occurred at the cyclohexylmethyl tail of the compound.[17]

See also

References
  1. "MAB-CHMINACA". Cayman Chemical. Retrieved 16 June 2015.
  2. "Patent WO/2009/106980 - Indazole derivatives". {{cite journal}}: Cite journal requires |journal= (help)
  3. Wurita A, Hasegawa K, Minakata K, Gonmori K, Nozawa H, Yamagishi I, Watanabe K, Suzuki O (July 2015). "Identification and quantitation of 5-fluoro-ADB-PINACA and MAB-CHMINACA in dubious herbal products". Forensic Toxicology. 33 (2): 213–220. doi:10.1007/s11419-015-0264-y. S2CID 207289143.
  4. Hasegawa K, Wurita A, Minakata K, Gonmori K, Nozawa H, Yamagishi I, et al. (July 2015). "Postmortem distribution of MAB-CHMINACA in body fluids and solid tissues of a human cadaver". Forensic Toxicology. 33 (2): 380–387. doi:10.1007/s11419-015-0272-y. PMC 4525191. PMID 26257834.
  5. Schwarz A (24 April 2015). "Potent 'Spice' Drug Fuels Rise in Visits to Emergency Room". The New York Times. Retrieved 29 June 2015.
  6. "American Association of Poison Control Centers Issues Warning About Reemerging Synthetic Drugs". American Association of Poison Control Centers. 23 April 2015. Retrieved 29 June 2015.
  7. "Synthetic cannabinoid users can exhibit bizarre and violent behaviors, hospitalizations after use increase in Alabama over past week" (PDF). Alabama Department of Public Health. 11 May 2015. Retrieved 29 June 2015.
  8. "Todesfälle in Zusammenhang mit ADB-CHMINACA". Drug Scouts. 7 May 2015. Retrieved 29 June 2015.
  9. Trecki J, Gerona RR, Schwartz MD (July 2015). "Synthetic Cannabinoid-Related Illnesses and Deaths". The New England Journal of Medicine. 373 (2): 103–7. doi:10.1056/NEJMp1505328. PMID 26154784.
  10. Collins D (8 May 2015). "There's Been A Sudden, Alarming Spike In Hospitalizations Caused By Synthetic Marijuana". Huffington Post. Retrieved 8 August 2015.
  11. Adamowicz P, Gieroń J (September 2016). "Acute intoxication of four individuals following use of the synthetic cannabinoid MAB-CHMINACA". Clinical Toxicology. 54 (8): 650–4. doi:10.1080/15563650.2016.1190016. PMID 27227269. S2CID 23133855.
  12. Drug Enforcement Administration, Department of Justice (January 2018). "Schedules of Controlled Substances: Extension of Temporary Placement of MAB–CHMINACA in Schedule I of the Controlled Substances Act. Temporary rule; temporary scheduling order; extension". Federal Register. 83 (20): 4411–2. PMID 29461023.
  13. "Gov. Jindal and State Officials Ban New Synthetic Marijuana Compound". Retrieved 16 June 2015.
  14. "Cannabinoider föreslås bli klassade som hälsofarlig vara". Folkhälsomyndigheten. Retrieved 29 June 2015.
  15. "CNB NEWS RELEASE". Central Narcotics Bureau (CNB). 30 April 2015. Archived from the original on 15 July 2015. Retrieved 24 July 2015.
  16. "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien". Der Bundesrat.
  17. Carlier J, Diao X, Sempio C, Huestis MA (March 2017). "Identification of New Synthetic Cannabinoid ADB-CHMINACA (MAB-CHMINACA) Metabolites in Human Hepatocytes". The AAPS Journal. 19 (2): 568–577. doi:10.1208/s12248-016-0037-5. PMID 28070717.
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