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Names

AMB-FUBINACA
MMB-FUBINACA
FUB-AMB

IUPAC names

Methyl N-{1-[(4-fluorophenyl)methyl]-1H-indazole-3-carbonyl}-L-valinate
Methyl (2S)-2-({1-[(4-fluorophenyl)methyl]-1H-indazole-3-carbonyl}amino)-3-methylbutanoate

ID 4522 · Formula C₂₁H₂₂FN₃O₃ · Molecular weight 383.416

Tags Cannabinoid

InChI InChI=1S/C21H22FN3O3/c1-13(2)18(21(27)28-3)23-20(26)19-16-6-4-5-7-17(16)25(24-19)12-14-8-10-15(22)11-9-14/h4-11,13,18H,12H2,1-3H3,(H,23,26)/t18-/m0/s1

InChI Key FRFFLYJQPCIIQB-SFHVURJKSA-N This stereoisomer Any stereoisomer

SMILES COC(=O)[C@H](C(C)C)NC(=O)c1nn(c2c1cccc2)Cc1ccc(cc1)F

ChemSpider 32741679
PubChem 119026173
Wikidata Q27290479
Wikipedia AMB-FUBINACA
Project Response FUB-AMB (1387-15)
forensicdrugreview.com FUB-AMB
aipsin.com FUB-AMB (Iss. 3, Jun-Sep 2019: VII-6)

Longworth, M; Banister, SD; Boyd, R; Kevin, RC; Connor, M; McGregor, IS; Kassiou, M. The pharmacology of cumyl-carboxamide synthetic cannabinoid new psychoactive substances (NPS) CUMYL-BICA, CUMYL-PICA, CUMYL-5F-PICA, CUMYL-5F-PINACA, and their analogues. ACS Chem. Neurosci., 9 Aug 2017, 8 (10), 2159-2167. 1.7 MB. https://doi.org/10.1021/acschemneuro.7b00267 #7

EMCDDA. New drugs in Europe, 2014, European Monitoring Centre for Drugs and Drug Addiction, Lisbon, 1 Jul 2015. 879 kB.

Hess, C; Murach, J; Krueger, L; Scharrenbroch, L; Unger, M; Madea, B; Sydow, K. Simultaneous detection of 93 synthetic cannabinoids by liquid chromatography-tandem mass spectrometry and retrospective application to real forensic samples. Drug Test. Anal., 1 May 2017, 9 (5), 721-733. 267 kB. https://doi.org/10.1002/dta.2030 #FUB AMB LC,MS

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. MMB-FUBINACA

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 #76

Banister, SD; Adams, A; Kevin, RC; Macdonald, C; Glass, M; Boyd, R; Connor, M; McGregor, IS; Havel, CM; Bright, SJ; Vilamala, MV; Lladanosa, CG; Barratt, MJ; Gerona, RR. Synthesis and pharmacology of new psychoactive substance 5F-CUMYL-P7AICA, a scaffold- hopping analog of synthetic cannabinoid receptor agonists 5F-CUMYL-PICA and 5F-CUMYL-PINACA. Drug Test. Anal., 1 Feb 2019, 11 (2), 279–291. 3.1 MB. https://doi.org/10.1002/dta.2491 #AMB-FUBINACA GC,MS,NMR

Banister, SD; Arnold, JC; Connor, M; Glass, M; McGregor, IS. Dark classics in chemical neuroscience: Δ⁹-Tetrahydrocannabinol. ACS Chem. Neurosci., 15 May 2019, 10 (5), 2160–2175. 1.8 MB. https://doi.org/10.1021/acschemneuro.8b00651 #12

Alam, RM; Keating, JJ. Adding more “spice” to the pot: A review of the chemistry and pharmacology of newly emerging heterocyclic synthetic cannabinoid receptor agonists. Drug Test. Anal., 1 Mar 2020, 12 (3), 297–315. 2.8 MB. https://doi.org/10.1002/dta.2752 #8 Structure 71 has a single bond where a double bond belongs

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 #FUB-AMB (AMB-FUBINACA)

Longworth, M; Reekie, TA; Blakey, K; Boyd, R; Connor, M; Kassiou, M. New-generation azaindole-adamantyl-derived synthetic cannabinoids. Forensic Toxicol., 1 Jul 2019, 37 (2), 350–365. 1.3 MB. https://doi.org/10.1007/s11419-019-00466-1 #5

Antonides, LH; Brignall, RM; Costello, A; Ellison, J; Firth, SE; Gilbert, N; Groom, BJ; Hudson, SJ; Hulme, MC; Marron, J; Pullen, ZA; Robertson, TBR; Schofield, CJ; Williamson, DC; Kemsley, EK; Sutcliffe, OB; Mewis, RE. Rapid identification of novel psychoactive and other controlled substances using low-field ¹H NMR spectroscopy. ACS Omega, 30 Apr 2019, 4 (4), 7103–7112. 1.3 MB. https://doi.org/10.1021/acsomega.9b00302 #AMB-FUBINACA NMR

Alam, RM; Keating, JJ. “Walking the nitrogen around the ring”: Chemical synthesis and spectroscopic characterization of novel 4‐, 5‐, 6‐, and 7‐azaindazole analogs of the synthetic cannabinoid receptor agonist MDMB‐PINACA. Drug Test. Anal., 11 Nov 2021, 14 (2), 277-297. 4.1 MB. https://doi.org/10.1002/dta.3180 #57 MS,NMR,IR,UV

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 #MMB-FUBINACA

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 #5 MS,NMR

Ametovski, A; Macdonald, C; Manning, JJ; Haneef, SAS; Santiago, M; Martin, L; Sparkes, E; Reckers, A; Gerona, RR; Connor, M; Glass, M; Banister, SD. Exploring stereochemical and conformational requirements at cannabinoid receptors for synthetic cannabinoids related to SDB-006, 5F-SDB-006, CUMYL-PICA, and 5F-CUMYL-PICA. ACS Chem. Neurosci., 4 Nov 2020, 11 (21), 3672–3682. 3.5 MB. https://doi.org/10.1021/acschemneuro.0c00591 #3 MS,NMR

MEP-FUBINACA

ADB-FUBINACA-COOH

7 Dec 2019 · · Isomer Design