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Names

AM-2201
JWH-2201
NA-5F-PIMO

IUPAC name

[1-(5-Fluoropentyl)-1H-indol-3-yl](naphthalen-1-yl)methanone

ID 4358 · Formula C₂₄H₂₂FNO · Molecular weight 359.436

Tags Cannabinoid

InChI InChI=1S/C24H22FNO/c25-15-6-1-7-16-26-17-22(20-12-4-5-14-23(20)26)24(27)21-13-8-10-18-9-2-3-11-19(18)21/h2-5,8-14,17H,1,6-7,15-16H2

InChI Key ALQFAGFPQCBPED-UHFFFAOYSA-N This stereoisomer Any stereoisomer

SMILES FCCCCCn1cc(c2c1cccc2)C(=O)c1cccc2c1cccc2

ChemSpider 24751884
PubChem 53393997
Wikidata Q4652489
Wikipedia AM-2201
Project Response AM-2201 (1478-16)
swgdrug.org AM-2201

EMCDDA. New drugs in Europe, 2011, European Monitoring Centre for Drugs and Drug Addiction, Lisbon, 1 Apr 2012. 401 kB.

Jones, LE; Stewart, A; Peters, KL; McNaul, M; Speers, SJ; Fletcher, NC; Bell, SEJ. Infrared and Raman screening of seized novel psychoactive substances: a large scale study of >200 samples. Analyst, 25 Jan 2016, 141 (3), 902–909. 1.3 MB. https://doi.org/10.1039/c5an02326b

Sobolevsky, T; Prasolov, I; Rodchenkov, G. Detection of urinary metabolites of AM-2201 and UR-144, two novel synthetic cannabinoids. Drug Test. Anal., 1 Jan 2012, 4 (10), 745-753. 779 kB. https://doi.org/10.1002/dta.1418

Dunne, SJ; Rosengren-Holmberg, JP. Quantification of synthetic cannabinoids in herbal smoking blends using NMR. Drug Test. Anal., 1 May 2017, 9 (5), 734-743. 988 kB. https://doi.org/10.1002/dta.2032

Gwak, S; Arroyo-Mora, LE; Almirall, JR. Qualitative analysis of seized synthetic cannabinoids and synthetic cathinones by gas chromatography triple quadrupole tandem mass spectrometry. Drug Test. Anal., 1 Feb 2015, 7 (2), 121-130. 1.1 MB. https://doi.org/10.1002/dta.1667 #24

Moosmann, B; Kneisel, S; Girreser, U; Brecht, V; Westphal, F; Auwärter, V. Separation and structural characterization of the synthetic cannabinoids JWH-412 and 1-[(5-fluoropentyl)-1H-indol-3-yl]-(4-methylnaphthalen-1-yl)methanone using GC–MS, NMR analysis and a flash chromatography system. Forensic Sci. Int., 1 Jul 2012, 220 (1-3), e17-e22. 675 kB. https://doi.org/10.1016/j.forsciint.2011.12.010

Kneisel, S; Auwärter, V; Kempf, J. Analysis of 30 synthetic cannabinoids in oral fluid using liquid chromatography-electrospray ionization tandem mass spectrometry. Drug Test. Anal., 1 Aug 2013, 5 (8), 657-669. 285 kB. https://doi.org/10.1002/dta.1429

Montenarh, D; Hopf, M; Warth, S; Maurer, HH; Schmidt, P; Ewald, AH. A simple extraction and LC-MS/MS approach for the screening and identification of over 100 analytes in eight different matrices: Detection of 130 analytes in eight biosamples using only one LC-MS/MS method. Drug Test. Anal., 1 Mar 2015, 7 (3), 214-240. 593 kB. https://doi.org/10.1002/dta.1657

Banister, SD; Connor, M. The chemistry and pharmacology of synthetic cannabinoid receptor agonists as new psychoactive substances: Origins. In New Psychoactive Substances: Pharmacology, Clinical, Forensic and Analytical Toxicology; Maurer, HH; Brandt, SD, Eds., Springer, Berlin, Heidelberg, 1 Jan 2018; pp 165-190. 906 kB. https://doi.org/10.1007/164_2018_143 #32

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 #2. AM-2201

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 #AM-2201

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 #4

Makriyannis, A; Deng, H. Cannabimimetic indole derivatives . Patent US 6900236, 31 May 2005. #AM2201

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 #4

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 #32

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 #AM-2201

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 #AM-2201

Anon. Ordinance amending the Annex to the New Psychoactive Substances Act [Neue-psychoaktive-Stoffe-Gesetz] as well as Annexes to the Narcotics Act [Betäubungsmittelgesetz]. 14 Mar 2019. 704 kB. #AM-2201

Meyers-Riggs, B. Halogenated and hyperpotent. countyourculture, countyourculture: rational exploration of the underground, 12 Jan 2011. #AM-2201

Wouters, E; Walraed, J; Robertson, MJ; Meyrath, M; Szpakowska, M; Chevigné, A; Skiniotis, G; Stove, C. Assessment of biased agonism among distinct synthetic cannabinoid receptor agonist scaffolds. ACS Pharmacol. Transl. Sci., 10 Apr 2020, 3 (2), 285–295. 2.0 MB. https://doi.org/10.1021/acsptsci.9b00069 #2

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 #AM-2201

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 #AM-2201

Kondrasenko, AA; Goncharov, EV; Dugaev, KP; Rubaylo, AI. CBL-2201. Report on a new designer drug: Napht-1-yl 1-(5-fluoropentyl)-1H-indole-3-carboxylate. Forensic Sci. Int., 1 Dec 2015, 257, 209–213. 319 kB. https://doi.org/10.1016/j.forsciint.2015.08.023 #AM-2201 MS,NMR,IR

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 #12

4F-NA-PIMO · JWH-412

WO 2014/015298 #63

WO 2014/015298 #64

WO 2014/015298 #65

WO 2014/015298 #62

7 Dec 2019 · · Isomer Design