AB-PINACA

Systematic (IUPAC) name
N-[(1S)-1-(aminocarbonyl)-2-methylpropyl]-1-pentyl-1H-indazole-3-carboxamide
Clinical data
Legal status	US: Schedule I
Identifiers
CAS Registry Number	1445752-09-9 Y
ChemSpider	28537615
Chemical data
Formula	C18H26N4O2
Molecular mass	330.43 g/mol
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

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

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

AB-PINACA acts as a potent agonist for the CB₁ receptor (K_i = 2.87 nM, EC₅₀ = 1.2 nM) and CB₂ receptor (K_i = 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]

Side effects[edit]

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

Legality[edit]

AB-PINACA is listed in Anlage II and therefore illegal in Germany as of November 2014.^[7]

AB-PINACA is listed in the Fifth Schedule of the Misuse of Drugs Act (MDA) and therefore illegal in Singapore as of May 2015.^[8]

It's a Schedule I controlled substance in the USA.^[9]

As of October 2015 AB-PINACA is a controlled substance in China.^[10]

See also[edit]

References[edit]

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. doi:10.1007/s11419-012-0171-4. 
2. ^ "AB-PINACA". Cayman Chemical. Retrieved 25 June 2015. 
3. ^ "Patent WO/2009/106980 - Indazole derivatives". 
4. ^ doi:10.1021/acschemneuro.5b00112
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5. ^ Jenny L Wiley, Julie A Marusich, Timothy W Lefever, Kateland R Antonazzo, Michael T Wallgren, Ricardo A Cortes, Purvi R Patel, Megan Grabenauer, Katherine N Moore, and Brian F Thomas (June 2015). "AB-CHMINACA, AB-PINACA, and FUBIMINA: Affinity and Potency of Novel Synthetic Cannabinoids in Producing Δ9-Tetrahydrocannabinol-Like Effects in Mice". Journal of Pharmacology and Experimental Therapeutics 354 (3): 328–39. doi:10.1124/jpet.115.225326. PMC 4538877. PMID 26105953. 
6. ^ Jordan Trecki, Roy R. Gerona, Michael D. Schwartz (July 2015). "Synthetic Cannabinoid–Related Illnesses and Deaths". New England Journal of Medicine 373 (2): 103–107. 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. 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. Retrieved 1 October 2015.