AB-PINACA

AB-PINACA
Legal status
Legal status	CA: Schedule II ; DE: Anlage II (Authorized trade only, not prescriptible) ; US: Schedule I ;
Identifiers
	IUPAC name N-[(1S)-1-(Aminocarbonyl)-2-methylpropyl]-1-pentyl-1H-indazole-3-carboxamide;
CAS Number	1445752-09-9 ;
PubChem CID	71301472;
ChemSpider	28537615;
UNII	6J3KC3S2PA;
Chemical and physical data
Formula	C18H26N4O2
Molar mass	330.432 g·mol−1
3D model (JSmol)	Interactive image;
	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 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]

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

Legal status

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 Status

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]

References

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.
"AB-PINACA". Cayman Chemical. Retrieved 25 June 2015.
"Patent WO/2009/106980 - Indazole derivatives". Cite journal requires |journal= (help)
Banister, Samuel D.; Moir, Michael; Stuart, Jordyn; Kevin, Richard C.; Wood, Katie E.; Longworth, Mitchell; Wilkinson, Shane M.; Beinat, Corinne; Buchanan, Alexandra S.; Glass, Michelle; Connor, Mark; McGregor, Iain S.; Kassiou, Michael (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.
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; 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.
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.
"Gesetz über den Verkehr mit Betäubungsmitteln (Betäubungsmittelgesetz - BtMG) Anlage II (zu § 1 Abs. 1) (verkehrsfähige, aber nicht verschreibungsfähige Betäubungsmittel)". Retrieved 22 June 2015.
"CNB NEWS RELEASE". Central Narcotics Bureau (CNB). 30 April 2015. Archived from the original on 15 July 2015. Retrieved 24 July 2015.
"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.
"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.
"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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[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.

[2] "AB-PINACA". Cayman Chemical. Retrieved 25 June 2015.

[3] "Patent WO/2009/106980 - Indazole derivatives". Cite journal requires |journal= (help)

[4] Banister, Samuel D.; Moir, Michael; Stuart, Jordyn; Kevin, Richard C.; Wood, Katie E.; Longworth, Mitchell; Wilkinson, Shane M.; Beinat, Corinne; Buchanan, Alexandra S.; Glass, Michelle; Connor, Mark; McGregor, Iain S.; Kassiou, Michael (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] 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; 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. 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. 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.