XLR-11

XLR-11
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics); 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;
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;

XLR-11 (5"-fluoro-UR-144 or 5F-UR-144) is a drug that acts as a potent

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]

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, effective from 13 July 2012.^[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.^[8]

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

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

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

XLR-11 is banned in the Czech Republic.^[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]

References

^ 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.
^
PMID 25921407
.

^ 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
PMID 19921781
.

^ "XLR-11". Structural, chemical, and analytical data on controlled substances. Southern Association of Forensic Scientists (SAFS).

doi:10.1071/CH14198
.

^ "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.

^ DEA. https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf. {{cite web}}: Missing or empty |title= (help)

^ "Attorney General Pam Bondi Outlaws Additional Synthetic Drugs" (Press release). State of Florida. 11 December 2012.

^ "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.

^ "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.

^ "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.

PMID 26154784
.

^ "Alphabet Soup, or the newer synthetic cannabinoids..." The Dose Makes The Poison Blog. 11 December 2013. Retrieved 18 September 2014.

PMID 23243266
.

^ "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.

Retrieved from "https://en.wikipedia.org/w/index.php?title=XLR-11&oldid=1201273123"

[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.

[doi10.1021/acschemneuro.5b00107-2] 
PMID 25921407
.

[WO2006/069196-3] 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

[pmid19921781-4] PMID 19921781
.

[url_forendex-5] "XLR-11". Structural, chemical, and analytical data on controlled substances. Southern Association of Forensic Scientists (SAFS).

[6] :10.1071/CH14198
.

[url_New_Zealand_Gazette-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. https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf. {{cite web}}: Missing or empty |title= (help)

[urlNews_Release_–_Attorney_General_Pam_Bondi_Outlaws_Additional_Synthetic_Drugs-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] PMID 26154784
.

[14] "Alphabet Soup, or the newer synthetic cannabinoids..." The Dose Makes The Poison Blog. 11 December 2013. Retrieved 18 September 2014.

[pmid23243266-15] PMID 23243266
.

[url_CDC-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.

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