XLR-11

This article is about the recreational drug. For the rocket motor, see Reaction Motors XLR11.

XLR-11 (5"-fluoro-UR-144 or 5F-UR-144) is a drug that acts as a potent agonist for the cannabinoid receptors CB₁ and CB₂ with EC₅₀ values of 98 nM and 83 nM, respectively.^[2] It is a 3-(tetramethylcyclopropylmethanoyl)indole derivative related to compounds such as UR-144, A-796,260 and A-834,735, but it is not specifically listed in the patent or scientific literature alongside these other similar compounds,^[3][4] and appears to have not previously been made by Abbott Laboratories, despite falling within the claims of patent WO 2006/069196. XLR-11 was found to produce rapid, short-lived hypothermic effects in rats at doses of 3 mg/kg and 10 mg/kg, suggesting that it is of comparable potency to APICA and STS-135.^[2]

XLR-11

Legal status
Legal status	BR: Class F2 (Prohibited psychotropics)[1] CA: Schedule II DE: Anlage II (Authorized trade only, not prescriptible) NZ: Temporary Class UK: Class B US: Schedule I
Identifiers
IUPAC name (1-(5-fluoropentyl)-1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone
CAS Number	1364933-54-9 Y
PubChem CID	57501498
ChemSpider	28537382
UNII	L2M8B977ZE
KEGG	C22770
CompTox Dashboard (EPA)	DTXSID00159825
Chemical and physical data
Formula	C21H28FNO
Molar mass	329.459 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC1(C(C1(C)C)C(=O)c2cn(c3c2cccc3)CCCCCF)C
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 Key:PXLDPUUMIHVLEC-UHFFFAOYSA-N

Detection

A forensic standard for this compound is available, and a representative mass spectrum has been posted on Forendex.^[5]

Recreational use

XLR-11 was instead first identified by laboratories in 2012 as an ingredient in synthetic cannabis smoking blends, and appears to be a novel compound invented specifically for grey-market recreational use.^[6]

Legal Status

XLR-11 was banned in New Zealand by being added to the temporary class drug schedule, as of 13 July 2012^[update].^[7]

The U.S. Drug Enforcement Administration (DEA) made XLR11 illegal under the Federal Controlled Substances act for the foreseeable future as of January 2024^[update].^[8]

It has also been banned in Florida as of 11 December 2012^[update].^[9]

Arizona banned XLR-11 on 3 April 2013.^[10]

As of October 2015^[update], XLR-11 is a controlled substance in China.^[11]

XLR-11 is banned in the Czech Republic.^{[as of?][12]}

Side effects

XLR-11 has been linked to hospitalizations due to its use.^[13]

Toxicity

XLR-11 has been linked to acute kidney injury in some users,^[14] along with AM-2201.^[15][16]

See also

• FAB-144
• JWH-018
• STS-135
• UR-144
• XLR-12

References

1. Anvisa (24 July 2023). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 25 July 2023). Archived from the original on 27 August 2023. Retrieved 27 August 2023.
2. Banister SD, Stuart J, Kevin RC, Edington A, Longworth M, Wilkinson SM, et al. (August 2015). "Effects of bioisosteric fluorine in synthetic cannabinoid designer drugs JWH-018, AM-2201, UR-144, XLR-11, PB-22, 5F-PB-22, APICA, and STS-135". ACS Chemical Neuroscience. 6 (8): 1445–1458. doi:10.1021/acschemneuro.5b00107. PMID 25921407.
3. WO application 2006069196, Pace JM, Tietje K, Dart MJ, Meyer MD, "3-Cycloalkylcarbonyl indoles as cannabinoid receptor ligands", published 2006-06-29, assigned to Abbott Laboratories
4. Frost JM, Dart MJ, Tietje KR, Garrison TR, Grayson GK, Daza AV, et al. (January 2010). "Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB(2) cannabinoid receptor activity". Journal of Medicinal Chemistry. 53 (1): 295–315. doi:10.1021/jm901214q. PMID 19921781.
5. "XLR-11". Structural, chemical, and analytical data on controlled substances. Southern Association of Forensic Scientists (SAFS).
6. Wilkinson SM, Banister SD, Kassiou M (2015). "Bioisosteric Fluorine in the Clandestine Design of Synthetic Cannabinoids". Australian Journal of Chemistry. 68: 4. doi:10.1071/CH14198.
7. "CB-13, MAM-2201, AKB48, and XLR11 are classified as temporary class drugs". Temporary Class Drug Notice. The Department of Internal Affairs: New Zealand Gazette. 5 July 2012.
8. DEA (April 2024). "Lists of: Scheduling Actions, Controlled Substances, Regulated Chemicals" (PDF). Archived from the original (PDF) on 5 May 2024. Retrieved 13 May 2024.
9. "Attorney General Pam Bondi Outlaws Additional Synthetic Drugs" (Press release). State of Florida. 11 December 2012.
10. "Governor Jan Brewer Signs Legislation to Combat Production, Use of Dangerous Drugs" (PDF) (Press release). Office of the Governor, State of Arizona. Archived from the original (PDF) on 7 June 2013. Retrieved 27 August 2014.
11. "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Retrieved 1 October 2015.
12. "Látky, o které byl doplněn seznam č. 4 psychotropních látek (příloha č. 4 k nařízení vlády č. 463/2013 Sb.)" (PDF) (in Czech). Ministerstvo zdravotnictví.
13. Trecki J, Gerona RR, Schwartz MD (July 2015). "Synthetic Cannabinoid-Related Illnesses and Deaths". The New England Journal of Medicine. 373 (2): 103–107. doi:10.1056/NEJMp1505328. PMID 26154784.
14. "Alphabet Soup, or the newer synthetic cannabinoids..." The Dose Makes The Poison Blog. 11 December 2013. Retrieved 18 September 2014.
15. Bhanushali GK, Jain G, Fatima H, Leisch LJ, Thornley-Brown D (April 2013). "AKI associated with synthetic cannabinoids: a case series". Clinical Journal of the American Society of Nephrology. 8 (4): 523–526. doi:10.2215/CJN.05690612. PMC 3613952. PMID 23243266.
16. "Acute Kidney Injury Associated with Synthetic Cannabinoid Use – Multiple States, 2012". Morbidity and Mortality Weekly Report. U.S. Centers for Disease Control and Prevention (CDC). 15 February 2013. Retrieved 15 February 2013.