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ADB-CHMINACA

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
ADB-CHMINACA
Legal status
Legal status
Identifiers
  • N-[(2S)-1-Amino-3,3-dimethyl-1-oxobutan-2-yl]-1-(cyclohexylmethyl)indazole-3-carboxamide
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC21H30N4O2
Molar mass370.497 g·mol−1
3D model (JSmol)
  • CC(C)(C)[C@H](NC(=O)c1nn(CC2CCCCC2)c3ccccc13)C(N)=O
  • 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

ADB-CHMINACA (also known asADMB-CHMINACA[3] andMAB-CHMINACA) is anindazole-basedsynthetic cannabinoid. It is a potentagonist of theCB1 receptor with a binding affinity ofKi = 0.289 nM and was originally developed byPfizer in 2009 as ananalgesic medication.[4][5] It was identified in cannabinoid blends in Japan in early 2015.[6]

Side effects

[edit]

There have been a number of reported cases of deaths and hospitalizations in relation to this synthetic cannabinoid.[7][8][9][10][11][12][13][14]

Legal status

[edit]

In the United States, ADB-CHMINACA is aSchedule I controlled substance.[15] Prior to its listing at the federal level in 2018, Louisiana placed ADB-CHMINACA on its Schedule I list by emergency scheduling in 2014.[16]

Sweden's public health agency suggested to classify ADB-CHMINACA as hazardous substance on November 10, 2014.[17]

ADB-CHMINACA is listed in the Fifth Schedule of the Misuse of Drugs Act (MDA) and therefore illegal in Singapore as of May 2015.[18]

ADB-CHMINACA is illegal in Switzerland as of December 2015.[19]

Metabolism

[edit]

Ten ADB-CHMINACA major metabolites were identified in several incubations with cryopreserved human hepatocytes. Most transformations occurred at the cyclohexylmethyl tail of the compound.[20]

See also

[edit]

References

[edit]
  1. ^Anvisa (2023-07-24)."RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).Diário Oficial da União (published 2023-07-25).Archived from the original on 2023-08-27. Retrieved2023-08-27.
  2. ^"Substance Details ADB-CHMINACA". Retrieved2024-01-22.
  3. ^Pulver B, Fischmann S, Gallegos A, Christie R (March 2023). "EMCDDA framework and practical guidance for naming synthetic cannabinoids".Drug Testing and Analysis.15 (3):255–276.doi:10.1002/dta.3403.PMID 36346325.
  4. ^"MAB-CHMINACA". Cayman Chemical. Retrieved16 June 2015.
  5. ^WO 2009/106980, Buchler IP, Hayes MJ, Hegde SG, Hockerman SL, Jones DE, Kortum SW, Rico JG, Tenbrink RE, Wu KK, "Indazole derivatives", published 3 September 2009, assigned to Pfizer Inc.. 
  6. ^Wurita A, Hasegawa K, Minakata K, Gonmori K, Nozawa H, Yamagishi I, et al. (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.
  7. ^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.
  8. ^Schwarz A (24 April 2015)."Potent 'Spice' Drug Fuels Rise in Visits to Emergency Room".The New York Times. Retrieved29 June 2015.
  9. ^"American Association of Poison Control Centers Issues Warning About Reemerging Synthetic Drugs". American Association of Poison Control Centers. 23 April 2015. Retrieved29 June 2015.
  10. ^"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. Retrieved29 June 2015.
  11. ^"Todesfälle in Zusammenhang mit ADB-CHMINACA". Drug Scouts. 7 May 2015. Retrieved29 June 2015.
  12. ^Trecki J, Gerona RR, Schwartz MD (July 2015). "Synthetic Cannabinoid-Related Illnesses and Deaths".The New England Journal of Medicine.373 (2):103–107.doi:10.1056/NEJMp1505328.PMID 26154784.
  13. ^Collins D (8 May 2015)."There's Been A Sudden, Alarming Spike In Hospitalizations Caused By Synthetic Marijuana".Huffington Post. Retrieved8 August 2015.
  14. ^Adamowicz P, Gieroń J (September 2016). "Acute intoxication of four individuals following use of the synthetic cannabinoid MAB-CHMINACA".Clinical Toxicology.54 (8):650–654.doi:10.1080/15563650.2016.1190016.PMID 27227269.S2CID 23133855.
  15. ^Drug Enforcement Administration (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):4411–4412.PMID 29461023.
  16. ^"Gov. Jindal and State Officials Ban New Synthetic Marijuana Compound". 29 October 2014. Retrieved16 June 2015.
  17. ^"Cannabinoider föreslås bli klassade som hälsofarlig vara". Folkhälsomyndigheten. Retrieved29 June 2015.
  18. ^"CNB NEWS RELEASE". Central Narcotics Bureau (CNB). 30 April 2015. Archived fromthe original on 15 July 2015. Retrieved24 July 2015.
  19. ^"Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien". Der Bundesrat.
  20. ^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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