AB-PINACA

AB-PINACA
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics); 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	1445752-09-9 ;
PubChem CID	71301472;
ChemSpider	28537615;
UNII	6J3KC3S2PA;
KEGG	C22704;
CompTox Dashboard (EPA)	DTXSID00904034 ;
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.^[2]

It was originally developed by Pfizer in 2009 as an analgesic medication.^[3]^[4]

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.^[5]^[6]

There have been a number of reported cases of deaths and hospitalizations in relation to this synthetic cannabinoid.^[7]^[8]

Legal status

Germany

AB-PINACA is an Anlage II controlled substance in Germany as of November 2014.^[9]

Singapore

It is listed in the Fifth Schedule of the Misuse of Drugs Act and so is illegal in Singapore, as of May 2015.^[10]

United States

It is a Schedule I controlled substance in the United States.^[11]

China

It is a controlled substance in China as of October 2015.^[12]

France

It is a controlled substance in France as of March 2017.^[13]

References

^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
^ 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 25242453.93-100&rft.date=2012&rft_id=info:doi/10.1007/s11419-012-0171-4&rft_id=https://api.semanticscholar.org/CorpusID:25242453#id-name=S2CID&rft.aulast=Uchiyama&rft.aufirst=N&rft.au=Matsuda, S&rft.au=Wakana, D&rft.au=Kikura-Hanajiri, R&rft.au=Goda, Y&rfr_id=info:sid/en.wikipedia.org:AB-PINACA" class="Z3988">
^ "AB-PINACA". Cayman Chemical. Retrieved 25 June 2015.
^ WO 2009106980A, Buchler IP, Hayes MJ, Hegde SG, Hockerman SL, Jones DE, Kortum SW, Rico JG, Tenbrink RE, Wu KK, "Indazole derivatives", published 3 September 2009, assigned to Pfizer Inc.
^ 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): 1546–1559. doi:10.1021/acschemneuro.5b00112. PMID 26134475.1546-1559&rft.date=2015-09&rft_id=info:doi/10.1021/acschemneuro.5b00112&rft_id=info:pmid/26134475&rft.aulast=Banister&rft.aufirst=SD&rft.au=Moir, M&rft.au=Stuart, J&rft.au=Kevin, RC&rft.au=Wood, KE&rft.au=Longworth, M&rft.au=Wilkinson, SM&rft.au=Beinat, C&rft.au=Buchanan, AS&rft.au=Glass, M&rft.au=Connor, M&rft.au=McGregor, IS&rft.au=Kassiou, M&rfr_id=info:sid/en.wikipedia.org:AB-PINACA" class="Z3988">
^ 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): 328–339. doi:10.1124/jpet.115.225326. PMC 4538877. PMID 26105953.328-339&rft.date=2015-09&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4538877#id-name=PMC&rft_id=info:pmid/26105953&rft_id=info:doi/10.1124/jpet.115.225326&rft.aulast=Wiley&rft.aufirst=JL&rft.au=Marusich, JA&rft.au=Lefever, TW&rft.au=Antonazzo, KR&rft.au=Wallgren, MT&rft.au=Cortes, RA&rft.au=Patel, PR&rft.au=Grabenauer, M&rft.au=Moore, KN&rft.au=Thomas, BF&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4538877&rfr_id=info:sid/en.wikipedia.org:AB-PINACA" class="Z3988">
^ Trecki J, Gerona RR, Schwartz MD (July 2015). "Synthetic Cannabinoid-Related Illnesses and Deaths". The New England Journal of Medicine. 373 (2): 103–107. doi:10.1056/NEJMp1505328. PMID 26154784.103-107&rft.date=2015-07&rft_id=info:doi/10.1056/NEJMp1505328&rft_id=info:pmid/26154784&rft.aulast=Trecki&rft.aufirst=J&rft.au=Gerona, RR&rft.au=Schwartz, MD&rfr_id=info:sid/en.wikipedia.org:AB-PINACA" class="Z3988">
^ Thornton SL, Akpunonu P, Glauner K, Hoehn KS, Gerona R (September 2015). "Unintentional Pediatric Exposure to a Synthetic Cannabinoid (AB-PINACA) Resulting in Coma and Intubation". Annals of Emergency Medicine. 66 (3): 343–344. doi:10.1016/j.annemergmed.2015.05.021. PMID 26304261.343-344&rft.date=2015-09&rft_id=info:doi/10.1016/j.annemergmed.2015.05.021&rft_id=info:pmid/26304261&rft.aulast=Thornton&rft.aufirst=SL&rft.au=Akpunonu, P&rft.au=Glauner, K&rft.au=Hoehn, KS&rft.au=Gerona, R&rfr_id=info:sid/en.wikipedia.org:AB-PINACA" class="Z3988">
^ "Gesetz über den Verkehr mit Betäubungsmitteln (Betäubungsmittelgesetz - BtMG) Anlage II (zu § 1 Abs. 1) (verkehrsfähige, aber nicht verschreibungsfähige Betäubungsmittel)" [Law on the Traffic in Narcotic Substances (Narcotics Act - BtMG) Annex II (to Section 1 Paragraph 1) (marketable but not prescription narcotics)]. Retrieved 22 June 2015.
^ "Misuse of Drugs Act". 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, U.S. 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" [Notice on Issuing the Measures for the Listing and Control of Non-Medicinal Narcotic Drugs and Psychotropic Substances] (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 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" [Order of March 31, 2017 amending the order of February 22, 1990 establishing the list of substances classified as narcotics] (in French). Legifrance. 6 April 2017. Retrieved 6 April 2017.

[1] Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.

[2] 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 25242453.93-100&rft.date=2012&rft_id=info:doi/10.1007/s11419-012-0171-4&rft_id=https://api.semanticscholar.org/CorpusID:25242453#id-name=S2CID&rft.aulast=Uchiyama&rft.aufirst=N&rft.au=Matsuda, S&rft.au=Wakana, D&rft.au=Kikura-Hanajiri, R&rft.au=Goda, Y&rfr_id=info:sid/en.wikipedia.org:AB-PINACA" class="Z3988">

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

[4] WO 2009106980A, Buchler IP, Hayes MJ, Hegde SG, Hockerman SL, Jones DE, Kortum SW, Rico JG, Tenbrink RE, Wu KK, "Indazole derivatives", published 3 September 2009, assigned to Pfizer Inc.

[5] 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): 1546–1559. doi:10.1021/acschemneuro.5b00112. PMID 26134475.1546-1559&rft.date=2015-09&rft_id=info:doi/10.1021/acschemneuro.5b00112&rft_id=info:pmid/26134475&rft.aulast=Banister&rft.aufirst=SD&rft.au=Moir, M&rft.au=Stuart, J&rft.au=Kevin, RC&rft.au=Wood, KE&rft.au=Longworth, M&rft.au=Wilkinson, SM&rft.au=Beinat, C&rft.au=Buchanan, AS&rft.au=Glass, M&rft.au=Connor, M&rft.au=McGregor, IS&rft.au=Kassiou, M&rfr_id=info:sid/en.wikipedia.org:AB-PINACA" class="Z3988">

[6] 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): 328–339. doi:10.1124/jpet.115.225326. PMC 4538877. PMID 26105953.328-339&rft.date=2015-09&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4538877#id-name=PMC&rft_id=info:pmid/26105953&rft_id=info:doi/10.1124/jpet.115.225326&rft.aulast=Wiley&rft.aufirst=JL&rft.au=Marusich, JA&rft.au=Lefever, TW&rft.au=Antonazzo, KR&rft.au=Wallgren, MT&rft.au=Cortes, RA&rft.au=Patel, PR&rft.au=Grabenauer, M&rft.au=Moore, KN&rft.au=Thomas, BF&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4538877&rfr_id=info:sid/en.wikipedia.org:AB-PINACA" class="Z3988">

[7] Trecki J, Gerona RR, Schwartz MD (July 2015). "Synthetic Cannabinoid-Related Illnesses and Deaths". The New England Journal of Medicine. 373 (2): 103–107. doi:10.1056/NEJMp1505328. PMID 26154784.103-107&rft.date=2015-07&rft_id=info:doi/10.1056/NEJMp1505328&rft_id=info:pmid/26154784&rft.aulast=Trecki&rft.aufirst=J&rft.au=Gerona, RR&rft.au=Schwartz, MD&rfr_id=info:sid/en.wikipedia.org:AB-PINACA" class="Z3988">

[8] Thornton SL, Akpunonu P, Glauner K, Hoehn KS, Gerona R (September 2015). "Unintentional Pediatric Exposure to a Synthetic Cannabinoid (AB-PINACA) Resulting in Coma and Intubation". Annals of Emergency Medicine. 66 (3): 343–344. doi:10.1016/j.annemergmed.2015.05.021. PMID 26304261.343-344&rft.date=2015-09&rft_id=info:doi/10.1016/j.annemergmed.2015.05.021&rft_id=info:pmid/26304261&rft.aulast=Thornton&rft.aufirst=SL&rft.au=Akpunonu, P&rft.au=Glauner, K&rft.au=Hoehn, KS&rft.au=Gerona, R&rfr_id=info:sid/en.wikipedia.org:AB-PINACA" class="Z3988">

[9] "Gesetz über den Verkehr mit Betäubungsmitteln (Betäubungsmittelgesetz - BtMG) Anlage II (zu § 1 Abs. 1) (verkehrsfähige, aber nicht verschreibungsfähige Betäubungsmittel)" [Law on the Traffic in Narcotic Substances (Narcotics Act - BtMG) Annex II (to Section 1 Paragraph 1) (marketable but not prescription narcotics)]. Retrieved 22 June 2015.

[10] "Misuse of Drugs Act". Central Narcotics Bureau (CNB). 30 April 2015. Archived from the original on 15 July 2015. Retrieved 24 July 2015.

[11] "Schedules of controlled substances: Temporary placement of three synthetic cannabinoids into schedule I. Final order" (PDF). Drug Enforcement Administration, U.S. Department of Justice. 30 January 2015. Retrieved 9 July 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" [Notice on Issuing the Measures for the Listing and Control of Non-Medicinal Narcotic Drugs and Psychotropic Substances] (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.

[13] "Arrêté du 31 mars 2017 modifiant l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants" [Order of March 31, 2017 amending the order of February 22, 1990 establishing the list of substances classified as narcotics] (in French). Legifrance. 6 April 2017. Retrieved 6 April 2017.

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