AB-PINACA

AB-PINACA is a compound that was first identified as a component of synthetic cannabis products in Japan in 2012.[1]

AB-PINACA
Legal status
Legal status
  • CA: Schedule II
  • DE: Anlage II (Authorized trade only, not prescriptible)
  • UK: Class B
  • US: Schedule I
Identifiers
IUPAC name
  • N-[(1S)-1-(Aminocarbonyl)-2-methylpropyl]-1-pentyl-1H-indazole-3-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H26N4O2
Molar mass330.432 g·mol−1
3D model (JSmol)
SMILES
  • CCCCCn1c2ccccc2c(n1)C(=O)N[C@@H](C(C)C)C(=O)N
InChI
  • InChI=1S/C18H26N4O2/c1-4-5-8-11-22-14-10-7-6-9-13(14)16(21-22)18(24)20-15(12(2)3)17(19)23/h6-7,9-10,12,15H,4-5,8,11H2,1-3H3,(H2,19,23)(H,20,24)/t15-/m0/s1
  • Key:GIMHPAQOAAZSHS-HNNXBMFYSA-N

It was originally developed by Pfizer in 2009 as an analgesic medication.[2][3]

AB-PINACA acts as a potent agonist for the CB1 receptor (Ki = 2.87 nM, EC50 = 1.2 nM) and CB2 receptor (Ki = 0.88 nM, EC50 = 2.5 nM) and fully substitutes for Δ9-THC in rat discrimination studies, while being 1.5x more potent.[4][5]

There have been a number of reported cases of deaths and hospitalizations in relation to this synthetic cannabinoid.[6]

Germany

AB-PINACA is an Anlage II controlled substance in Germany as of November 2014.[7]

Singapore

It is listed in the Fifth Schedule of the Misuse of Drugs Act and so is illegal in Singapore, as of May 2015.[8]

United States

It is a Schedule I controlled substance in the United States.[9]

China

It is a controlled substance in China as of October 2015.[10]

France

It is a controlled substance in France as of March 2017.[11]

See also

References
  1. Uchiyama N, Matsuda S, Wakana D, Kikura-Hanajiri R, Goda Y (2012). "New cannabimimetic indazole derivatives, N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-pentyl-1H-indazole-3-carboxamide (AB-PINACA) and N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-(4-fluorobenzyl)-1H-indazole-3-carboxamide (AB-FUBINACA) identified as designer drugs in illegal products". Forensic Toxicology. 31: 93–100. doi:10.1007/s11419-012-0171-4. S2CID 25242453.
  2. "AB-PINACA". Cayman Chemical. Retrieved 25 June 2015.
  3. "Patent WO/2009/106980 - Indazole derivatives". {{cite journal}}: Cite journal requires |journal= (help)
  4. Banister SD, Moir M, Stuart J, Kevin RC, Wood KE, Longworth M, et al. (September 2015). "Pharmacology of Indole and Indazole Synthetic Cannabinoid Designer Drugs AB-FUBINACA, ADB-FUBINACA, AB-PINACA, ADB-PINACA, 5F-AB-PINACA, 5F-ADB-PINACA, ADBICA, and 5F-ADBICA". ACS Chemical Neuroscience. 6 (9): 1546–59. doi:10.1021/acschemneuro.5b00112. PMID 26134475.
  5. 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.
  6. 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.
  7. "Gesetz über den Verkehr mit Betäubungsmitteln (Betäubungsmittelgesetz - BtMG) Anlage II (zu § 1 Abs. 1) (verkehrsfähige, aber nicht verschreibungsfähige Betäubungsmittel)". Retrieved 22 June 2015.
  8. "CNB NEWS RELEASE". Central Narcotics Bureau (CNB). 30 April 2015. Archived from the original on 15 July 2015. Retrieved 24 July 2015.
  9. "Schedules of controlled substances: Temporary placement of three synthetic cannabinoids into schedule I. Final order" (PDF). Drug Enforcement Administration, Department of Justice. 30 January 2015. Retrieved 9 July 2015.
  10. "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.
  11. "Arrêté du 31 mars 2017 modifiant l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants" (in French). Legifrance. 6 April 2017. Retrieved 6 April 2017.
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