AB-CHMINACA

AB-CHMINACA is an indazole-based synthetic cannabinoid. It is a potent agonist of the CB1 receptor (Ki = 0.78 nM) and CB2 receptor (Ki = 0.45 nM) and fully substitutes for Δ9-THC in rat discrimination studies, while being 16x more potent.[1][2] Continuing the trend seen in other cannabinoids of this generation, such as AB-FUBINACA and AB-PINACA, it contains a valine amino acid amide residue as part of its structure, where older cannabinoids contained a naphthyl or adamantane residue.

AB-CHMINACA
Legal status
Legal status
  • CA: Schedule II
  • DE: Anlage II (Authorized trade only, not prescriptible)
  • UK: Class B
  • US: Schedule I
  • Illegal in China and Switzerland
Identifiers
IUPAC name
  • N-[(2S)-1-Amino-3-methyl-1-oxobutan-2-yl]-1-(cyclohexylmethyl)indazole-3-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H28N4O2
Molar mass356.470 g·mol−1
3D model (JSmol)
SMILES
  • CC(C)[C@H](NC(=O)c1nn(CC2CCCCC2)c3ccccc13)C(N)=O
InChI
  • InChI=1S/C20H28N4O2/c1-13(2)17(19(21)25)22-20(26)18-15-10-6-7-11-16(15)24(23-18)12-14-8-4-3-5-9-14/h6-7,10-11,13-14,17H,3-5,8-9,12H2,1-2H3,(H2,21,25)(H,22,26)/t17-/m0/s1
  • Key:KJNZIEGLNLCWTQ-KRWDZBQOSA-N

Side effects

There have been a number of reported cases of seizures, deaths, and psychotic episodes in relation to this synthetic cannabinoid.[3][4][5][6][7][8][9]

In 2015, AB-CHMINACA became a Schedule I controlled substance in the United States.[10]

AB-CHMINACA is an Anlage II controlled substance in Germany as of May 2015.[11]

As of October 2015 AB-CHMINACA is a controlled substance in China.[12]

AB-CHMINACA is illegal in Switzerland as of December 2015.[13]

AB-CHMINACA is an illegal substance in Russian Federation.

See also

References
  1. Wiley JL, Marusich JA, Lefever TW, Antonazzo KR, Wallgren MT, Cortes RA, et al. (September 2015). "AB-CHMINACA, AB-PINACA, and FUBIMINA: Affinity and Potency of Novel Synthetic Cannabinoids in Producing Δ9-Tetrahydrocannabinol-Like Effects in Mice". The Journal of Pharmacology and Experimental Therapeutics. 354 (3): 328–39. doi:10.1124/jpet.115.225326. PMC 4538877. PMID 26105953.
  2. AB-CHMINACA, Cayman Chemicals
  3. "N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-(cyclohexylmethyl)-1H-indazole-3-carboxamide (AB-CHMINACA), N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-pentyl-1H-indazole-3-carboxamide (AB-PINACA) and [1-(5-fluoropentyl)-1H-indazol-3-yl](naphthalen-1-yl)methanone (THJ-2201). Background Information and Evaluation of 'Three Factor Analysis' (Factors 4, 5, and 6) for Temporary Scheduling" (PDF). Drug Enforcement Administration. December 2014. Retrieved 7 August 2015.
  4. Merrill J (5 June 2015). "Vertex: Police warn of 'ticking time bomb' of potentially lethal cannabis substitute". The Independent. Archived from the original on 2015-06-05. Retrieved 2 July 2015.
  5. 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.
  6. Wurita A, Hasegawa K, Minakata K, Gonmori K, Nozawa H, Yamagishi I, et al. (March 2016). "Identification and quantification of metabolites of AB-CHMINACA in a urine specimen of an abuser". Legal Medicine. 19: 113–8. doi:10.1016/j.legalmed.2015.07.011. PMID 26257317.
  7. Schock B (30 September 2015). "No criminal charges in March death of Terrance Moxley". Richland Source. Retrieved 2 October 2015.
  8. Tyndall JA, Gerona R, De Portu G, Trecki J, Elie MC, Lucas J, et al. (November 2015). "An outbreak of acute delirium from exposure to the synthetic cannabinoid AB-CHMINACA". Clinical Toxicology. 53 (10): 950–6. doi:10.3109/15563650.2015.1100306. PMID 26555732. S2CID 24724258.
  9. Klavž J, Gorenjak M, Marinšek M (August 2016). "Suicide attempt with a mix of synthetic cannabinoids and synthetic cathinones: Case report of non-fatal intoxication with AB-CHMINACA, AB-FUBINACA, alpha-PHP, alpha-PVP and 4-CMC". Forensic Science International. 265: 121–4. doi:10.1016/j.forsciint.2016.01.018. PMID 26890319.
  10. Drug Enforcement Administration, Department of Justice (January 2015). "Schedules of controlled substances: temporary placement of three synthetic cannabinoids into schedule I. Final order" (PDF). Federal Register. 80 (20): 5042–7. PMID 25730924.
  11. "Gesetz über den Verkehr mit Betäubungsmitteln (Betäubungsmittelgesetz - BtMG) Anlage II (zu § 1 Abs. 1) (verkehrsfähige, aber nicht verschreibungsfähige Betäubungsmittel)". Retrieved 22 June 2015.
  12. "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
  13. "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien". Der Bundesrat.
  14. Cannaert A, Sparkes E, Pike E, Luo JL, Fang A, Kevin RC, et al. (November 2020). "in Vitro Cannabinoid Receptor 1 Activity of Recently Detected Synthetic Cannabinoids 4F-MDMB-BICA, 5F-MPP-PICA, MMB-4en-PICA, CUMYL-CBMICA, ADB-BINACA, APP-BINACA, 4F-MDMB-BINACA, MDMB-4en-PINACA, A-CHMINACA, 5F-AB-P7AICA, 5F-MDMB-P7AICA, and 5F-AP7AICA". ACS Chemical Neuroscience. 11 (24): 4434–4446. doi:10.1021/acschemneuro.0c00644. PMID 33253529. S2CID 227246346.
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