:AB-PINACA

{{Short description|Chemical compound}}

{{Drugbox

| IUPAC_name = N-[(1S)-1-(Aminocarbonyl)-2-methylpropyl]-1-pentyl-1H-indazole-3-carboxamide

| image = AB-PINACA_structure-rev1.png

| image_class = skin-invert-image

| tradename =

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_BR = F2

| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-07-25}}

| legal_CA = Schedule II

| legal_UK = Class B

| legal_US = Schedule I

| legal_DE = Anlage II

| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 1445752-09-9

| ATC_prefix =

| ATC_suffix =

| PubChem = 71301472

| KEGG = C22704

| ChemSpiderID = 28537615

| smiles = CCCCCn1c2ccccc2c(n1)C(=O)N[C@@H](C(C)C)C(=O)N

| StdInChI = 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

| StdInChIKey = GIMHPAQOAAZSHS-HNNXBMFYSA-N

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 6J3KC3S2PA

| C=18 | H=26 | N=4 | O=2

}}

AB-PINACA is a compound that was first identified as a component of synthetic cannabis products in Japan in 2012.{{Cite journal | vauthors = Uchiyama N, Matsuda S, Wakana D, Kikura-Hanajiri R, Goda Y | title = 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 | doi = 10.1007/s11419-012-0171-4 | journal = Forensic Toxicology | volume = 31 | pages = 93–100 | year = 2012 | s2cid = 25242453 }}

It was originally developed by Pfizer in 2009 as an analgesic medication.{{cite web | url=https://www.caymanchem.com/app/template/Product.vm/catalog/14038 | title=AB-PINACA| publisher=Cayman Chemical | access-date=25 June 2015}}{{cite patent | url=https://www.google.com/patents/WO2009106980A3 | country = WO | number = 2009106980A | title= Indazole derivatives | inventor = Buchler IP, Hayes MJ, Hegde SG, Hockerman SL, Jones DE, Kortum SW, Rico JG, Tenbrink RE, Wu KK | assign1 = Pfizer Inc. | pubdate = 3 September 2009 }}

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.{{cite journal | vauthors = Banister SD, Moir M, Stuart J, Kevin RC, Wood KE, Longworth M, Wilkinson SM, Beinat C, Buchanan AS, Glass M, Connor M, McGregor IS, Kassiou M | display-authors = 6 | title = 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 | journal = ACS Chemical Neuroscience | volume = 6 | issue = 9 | pages = 1546–1559 | date = September 2015 | pmid = 26134475 | doi = 10.1021/acschemneuro.5b00112 }}{{cite journal | vauthors = Wiley JL, Marusich JA, Lefever TW, Antonazzo KR, Wallgren MT, Cortes RA, Patel PR, Grabenauer M, Moore KN, Thomas BF | display-authors = 6 | title = AB-CHMINACA, AB-PINACA, and FUBIMINA: Affinity and Potency of Novel Synthetic Cannabinoids in Producing Δ9-Tetrahydrocannabinol-Like Effects in Mice | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 354 | issue = 3 | pages = 328–339 | date = September 2015 | pmid = 26105953 | pmc = 4538877 | doi = 10.1124/jpet.115.225326 }}

There have been a number of reported cases of deaths and hospitalizations in relation to this synthetic cannabinoid.{{cite journal | vauthors = Trecki J, Gerona RR, Schwartz MD | title = Synthetic Cannabinoid-Related Illnesses and Deaths | journal = The New England Journal of Medicine | volume = 373 | issue = 2 | pages = 103–107 | date = July 2015 | pmid = 26154784 | doi = 10.1056/NEJMp1505328 }}{{cite journal | vauthors = Thornton SL, Akpunonu P, Glauner K, Hoehn KS, Gerona R | title = Unintentional Pediatric Exposure to a Synthetic Cannabinoid (AB-PINACA) Resulting in Coma and Intubation | journal = Annals of Emergency Medicine | volume = 66 | issue = 3 | pages = 343–344 | date = September 2015 | pmid = 26304261 | doi = 10.1016/j.annemergmed.2015.05.021 }}