Chemistry:ADB-CHMINACA

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Short description: Chemical compound
ADB-CHMINACA
ADB-CHMINACA-fixed.svg
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
Chemical and physical data
FormulaC21H30N4O2
Molar mass370.497 g·mol−1
3D model (JSmol)

ADB-CHMINACA (also known as ADMB-CHMINACA[2] and 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.[3][4] It was identified in cannabinoid blends in Japan in early 2015.[5]

Side effects

There have been a number of reported cases of deaths and hospitalizations in relation to this synthetic cannabinoid.[6][7][8][9][10][11][12][13]

Legal status

In the United States, ADB-CHMINACA is a Schedule I controlled substance.[14] Prior to its listing at the federal level in 2018, Louisiana placed ADB-CHMINACA on its Schedule I list by emergency scheduling in 2014.[15]

Sweden's public health agency suggested to classify ADB-CHMINACA as hazardous substance on November 10, 2014.[16]

ADB-CHMINACA is listed in the Fifth Schedule of the Misuse of Drugs Act (MDA) and therefore illegal in Singapore as of May 2015.[17]

ADB-CHMINACA is illegal in Switzerland as of December 2015.[18]

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.[19]

See also


References

  1. "Substance Details ADB-CHMINACA". https://www.unodc.org/LSS/Substance/Details/c3c5f5b0-9f29-4fa9-a341-eea44ea193c2. 
  2. Pulver, Benedikt; Fischmann, Svenja; Gallegos, Ana; Christie, Rachel (March 2023). "EMCDDA framework and practical guidance for naming synthetic cannabinoids". Drug Testing and Analysis 15 (3): 255–276. doi:10.1002/dta.3403. 
  3. "MAB-CHMINACA". Cayman Chemical. https://www.caymanchem.com/app/template/Product.vm/catalog/16616. 
  4. Buchler IP, Hayes MJ, Hegde SG, Hockerman SL, Jones DE, Kortum SW, Rico JG, Tenbrink RE, Wu KK, "Indazole derivatives", WO patent 2009/106980, published 3 September 2009, assigned to Pfizer Inc..
  5. "Identification and quantitation of 5-fluoro-ADB-PINACA and MAB-CHMINACA in dubious herbal products". Forensic Toxicology 33 (2): 213–220. July 2015. doi:10.1007/s11419-015-0264-y. 
  6. "Postmortem distribution of MAB-CHMINACA in body fluids and solid tissues of a human cadaver". Forensic Toxicology 33 (2): 380–387. July 2015. doi:10.1007/s11419-015-0272-y. PMID 26257834. 
  7. "Potent 'Spice' Drug Fuels Rise in Visits to Emergency Room". The New York Times. 24 April 2015. https://www.nytimes.com/2015/04/25/health/surge-in-hospital-visits-linked-to-a-drug-called-spice-alarms-health-officials.html. 
  8. "American Association of Poison Control Centers Issues Warning About Reemerging Synthetic Drugs". American Association of Poison Control Centers. 23 April 2015. http://www.aapcc.org/press/43/. 
  9. "Synthetic cannabinoid users can exhibit bizarre and violent behaviors, hospitalizations after use increase in Alabama over past week". Alabama Department of Public Health. 11 May 2015. http://www.adph.org/news/assets/150511.pdf. 
  10. "Todesfälle in Zusammenhang mit ADB-CHMINACA". Drug Scouts. 7 May 2015. http://www.drugscouts.de/de/pillenwarnung/todesf%C3%A4lle-zusammenhang-mit-adb-chminaca. 
  11. "Synthetic Cannabinoid-Related Illnesses and Deaths". The New England Journal of Medicine 373 (2): 103–107. July 2015. doi:10.1056/NEJMp1505328. PMID 26154784. 
  12. "There's Been A Sudden, Alarming Spike In Hospitalizations Caused By Synthetic Marijuana". Huffington Post. 8 May 2015. http://www.huffingtonpost.com/2015/05/08/synthetic-marijuana-hospitalizations_n_7241772.html. 
  13. "Acute intoxication of four individuals following use of the synthetic cannabinoid MAB-CHMINACA". Clinical Toxicology 54 (8): 650–654. September 2016. doi:10.1080/15563650.2016.1190016. PMID 27227269. 
  14. "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): 4411–4412. January 2018. PMID 29461023. 
  15. "Gov. Jindal and State Officials Ban New Synthetic Marijuana Compound". http://dhh.louisiana.gov/index.cfm/newsroom/detail/3161. 
  16. "Cannabinoider föreslås bli klassade som hälsofarlig vara". Folkhälsomyndigheten. http://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2014/november/cannabinoider-foreslas-bli-klassade-som-halsofarlig-vara/. 
  17. "CNB NEWS RELEASE". Central Narcotics Bureau (CNB). 30 April 2015. http://www.cnb.gov.sg/Libraries/CNB_Newsroom_Files/CNB_NR_-_30_Apr_2015.sflb.ashx. 
  18. "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien". Der Bundesrat. https://www.admin.ch/opc/de/classified-compilation/20101220/index.html. 
  19. "Identification of New Synthetic Cannabinoid ADB-CHMINACA (MAB-CHMINACA) Metabolites in Human Hepatocytes". The AAPS Journal 19 (2): 568–577. March 2017. doi:10.1208/s12248-016-0037-5. PMID 28070717.