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Names

AB-PINACA
AMB-PINACA

IUPAC name

N-[(2S)-1-Amino-3-methyl-1-oxobutan-2-yl]-1-pentyl-1H-indazole-3-carboxamide

ID 4483 · Formula C₁₈H₂₆N₄O₂ · Molecular weight 330.425

Tags Cannabinoid

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

InChI Key GIMHPAQOAAZSHS-HNNXBMFYSA-N This stereoisomer Any stereoisomer

SMILES CCCCCn1nc(c2c1cccc2)C(=O)N[C@H](C(=O)N)C(C)C

ChemSpider 28537615
PubChem 71301472
Wikidata Q4650003
Wikipedia AB-PINACA
Project Response AB-PINACA (1221-15)
swgdrug.org AB-PINACA

Longworth, M; Banister, SD; Mack, JBC; Glass, M; Connor, M; Kassiou, M. The 2-alkyl-2H-indazole regioisomers of synthetic cannabinoids AB-CHMINACA, AB-FUBINACA, AB-PINACA, and 5F-AB-PINACA are possible manufacturing impurities with cannabimimetic activities. Forensic Toxicol., 1 Jul 2016, 34 (2), 286–303. 1.3 MB. https://doi.org/10.1007/s11419-016-0316-y #5

EMCDDA. New drugs in Europe, 2015, European Monitoring Centre for Drugs and Drug Addiction, Lisbon, 1 May 2016. 1.0 MB. #31

EMCDDA. New drugs in Europe, 2013, European Monitoring Centre for Drugs and Drug Addiction, Lisbon, 1 Jul 2014. 311 kB.

Smolianitski-Fabian, E; Cohen, E; Dronova, M; Voloshenko-Rossin, A; Lev, O. Discrimination between closely related synthetic cannabinoids by GC-Cold-EI-MS. Drug Test. Anal., 1 Mar 2018, 10 (3), 474-487. 1.3 MB. https://doi.org/10.1002/dta.2247

Zawilska, JB; Andrzejczak, D. Next generation of novel psychoactive substances on the horizon – A complex problem to face. Drug Alcohol Depend., 1 Jan 2015, 157, 1-17. 3.0 MB. https://doi.org/10.1016/j.drugalcdep.2015.09.030

Abbate, V; Schwenk, M; Presley, BC; Uchiyama, N. The ongoing challenge of novel psychoactive drugs of abuse. Part I. Synthetic cannabinoids (IUPAC Technical Report). Pure Appl. Chem., 28 Aug 2018, 90 (8), 1255–1282. 1.0 MB. https://doi.org/10.1515/pac-2017-0605 #8. AB-PINACA

Davidson, C; Opacka-Juffry, J; Arevalo-Martin, A; Garcia-Ovejero, D; Molina-Holgado, E; Molina-Holgado, F. Spicing up pharmacology: A review of synthetic cannabinoids from structure to adverse events. In Adv. Pharmacol.; , Elsevier, 1 Jan 2017; pp 135–168. 458 kB. https://doi.org/10.1016/bs.apha.2017.05.001 #AB-PINACA

Noble, C; Cannaert, A; Linnet, K; Stove, CP. Application of an activity-based receptor bioassay to investigate the in vitro activity of selected indole- and indazole-3-carboxamide-based synthetic cannabinoids at CB1 and CB2 receptors. Drug Test. Anal., 2 Oct 2018, 11 (3), 501-511. 935 kB. https://doi.org/10.1002/dta.2517 #10

EMCDDA. Report on the risk assessment of N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-(cyclohexylmethyl)-1H-indazole-3-carboxamide (AB-CHMINACA), European Monitoring Centre for Drugs and Drug Addiction, Lisbon, 1 Jul 2018. 831 kB. #AB-PINACA IR,UV

Banister, SD; Connor, M. The chemistry and pharmacology of synthetic cannabinoid receptor agonist new psychoactive substances: Evolution. In New Psychoactive Substances: Pharmacology, Clinical, Forensic and Analytical Toxicology; Maurer, HH; Brandt, SD, Eds., Springer, Berlin, Heidelberg, 1 Jan 2018; pp 191-226. 1.2 MB. https://doi.org/10.1007/164_2018_144 #52

Wilkinson, SM; Banister, SD; Kassiou, M. Bioisosteric fluorine in the clandestine design of synthetic cannabinoids. Aust. J. Chem., 10 Feb 2015, 68 (1), 4–8. 451 kB. https://doi.org/10.1071/CH14198 #27

Kronstrand, R; Guerrieri, D; Vikingsson, S; Wohlfarth, A; Gréen, H. Fatal poisonings associated with new psychoactive substances. In New Psychoactive Substances: Pharmacology, Clinical, Forensic and Analytical Toxicology; Maurer, HH; Brandt, SD, Eds., Springer, Berlin, Heidelberg, 1 Jan 2018; pp 495–541. 477 kB. https://doi.org/10.1007/164_2018_110 #AB-PINACA

Kraemer, M; Boehmer, A; Madea, B; Maas, A. Death cases involving certain new psychoactive substances: A review of the literature. Forensic Sci. Int., 1 May 2019, 298, 186–267. 6.7 MB. https://doi.org/10.1016/j.forsciint.2019.02.021 #AB-PINACA

Kikura-Hanajiri, R. New designer drugs in japan. In Neuropathology of Drug Addictions and Substance Misuse; Preedy, VR, Ed., Academic Press, 1 Jan 2016; pp 1055–1065. 682 kB. https://doi.org/10.1016/B978-0-12-800212-4.00097-2 #AB-PINACA

Åstrand, A; Guerrieri, D; Vikingsson, S; Kronstrand, R; Green, H. In vitro characterization of new psychoactive substances at the μ-opioid, CB1, 5HT_1A, and 5-HT2_A receptors—On-target receptor potency and efficacy, and off-target effects. Forensic Sci. Int., 1 Dec 2020, 317, 110553. 1.7 MB. https://doi.org/10.1016/j.forsciint.2020.110553 #AB-PINACA

Worob, A; Wenthur, C. DARK classics in chemical neuroscience: Synthetic cannabinoids (Spice/K2). ACS Chem. Neurosci., 2 Dec 2020, 11 (23), 3881–3892. 1.5 MB. https://doi.org/10.1021/acschemneuro.9b00586 #24

Wagmann, L; Stiller, RG; Fischmann, S; Westphal, F; Meyer, MR. Going deeper into the toxicokinetics of synthetic cannabinoids: In vitro contribution of human carboxylesterases. Arch. Toxicol., 1 Nov 2022, 96 (10), 2755–2766. 1.6 MB. https://doi.org/10.1007/s00204-022-03332-z #AB-PINACA

Kevin, RC; Mirlohi, S; Manning, JJ; Boyd, R; Cairns, EA; Ametovski, A; Lai, F; Luo, JL; Jorgensen, W; Ellison, R; Gerona, RR; Hibbs, DE; McGregor, IS; Glass, M; Connor, M; Bladen, C; Zamponi, GW; Banister, SD. Putative synthetic cannabinoids MEPIRAPIM, 5F-BEPIRAPIM (NNL-2), and their analogues are T-type calcium channel (Ca_V3) inhibitors. ACS Chem. Neurosci., 4 May 2022, 13 (9), 1395–1409. 4.5 MB. https://doi.org/10.1021/acschemneuro.1c00822 #3 MS,NMR

(2H-Indazole) AB-PINACA · AB-2PINACA

ADB-BINACA · ADB-BUTINACA · ADMB-BINACA

AEP-PINACA

7 Dec 2019 · · Isomer Design