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Names

5F-UR-144
XLR-11
5″-Fluoro-UR-144
TMCP-5F-PIMO

IUPAC name

[1-(5-Fluoropentyl)-1H-indol-3-yl](2,2,3,3-tetramethylcyclopropyl)methanone

ID 4676 · Formula C₂₁H₂₈FNO · Molecular weight 329.452

Tags Cannabinoid

InChI InChI=1S/C21H28FNO/c1-20(2)19(21(20,3)4)18(24)16-14-23(13-9-5-8-12-22)17-11-7-6-10-15(16)17/h6-7,10-11,14,19H,5,8-9,12-13H2,1-4H3

InChI Key PXLDPUUMIHVLEC-UHFFFAOYSA-N This stereoisomer Any stereoisomer

SMILES FCCCCCn1cc(c2c1cccc2)C(=O)C1C(C1(C)C)(C)C

ChemSpider 28537382
PubChem 57501498
Wikidata Q8042267
Wikipedia XLR-11
Project Response XLR-11 (1340-16)
forensicdrugreview.com XLR11 & Fluoroalkyl Analogs
swgdrug.org XLR-11

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 #2

EMCDDA. New drugs in Europe, 2012, European Monitoring Centre for Drugs and Drug Addiction, Lisbon, 1 May 2013. 773 kB. #22

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 NMR,other

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 #XLR-11 MS

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

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 #XLR-11 LC,MS

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 #9 GC,MS

Uchiyama, N; Kawamura, M; Kikura-Hanajiri, R; Goda, Y. URB-754: A new class of designer drug and 12 synthetic cannabinoids detected in illegal products Forensic Sci. Int., 10 Apr 2013, 227 (1), 21-32. 1.8 MB. https://doi.org/10.1016/j.forsciint.2012.08.047 #VII LC,MS,NMR,UV

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 #66

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 #5. XLR-11

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 #XLR-11

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 #13

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 #45

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 #XLR-11

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 #XLR-11

Patel, M; Manning, JJ; Finlay, DB; Javitch, JA; Banister, SD; Grimsey, NL; Glass, M. Signalling profiles of a structurally diverse panel of synthetic cannabinoid receptor agonists Biochem. Pharmacol., 1 May 2020, 175 113871. 1.9 MB. https://doi.org/10.1016/j.bcp.2020.113871 #XLR-11

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 #8

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 #XLR-11

Poyner, B; Spangler, M; Morris, JA; Stenzel, J. Analytical profile of three cyclopropanoyl indole cannabinoids JCLIC, 1 Mar 2013, 23 (2-3), 6-13. 1.9 MB. GC,MS,NMR,IR

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 #2 MS,NMR,IR,UV

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 #17

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 #2 MS,NMR

Langer, N; Lindigkeit, R; Schiebel, H; Ernst, L; Beuerle, T. Identification and quantification of synthetic cannabinoids in 'spice-like' herbal mixtures: A snapshot of the German situation in the autumn of 2012 Drug Test. Anal., 1 Jan 2014, 6 (1-2), 59-71. 1.7 MB. https://doi.org/10.1002/dta.1499 #XLR-11 MS,NMR

Andrews, R; Jorge, R; Christie, R; Gallegos, A. From JWH‐018 to OXIZIDS: Structural evolution of synthetic cannabinoids in the European Union from 2008 to present day Drug Test. Anal., 1 Apr 2023, 15 (4), 378–387. 1.2 MB. https://doi.org/10.1002/dta.3422 #XLR-11

(2-Fluoropentyl) XLR-11

7189

XLR11-N-(3-fluoropentyl) isomer

XLR11-N-(4-fluoropentyl) isomer

7 Dec 2019 · · Isomer Design