AB-CHMINACA

AB-CHMINACA
Legal status
Legal status
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

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.

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. 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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