XLR-11

Overview

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. 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, 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.[1][2][3] WP

Uses, dosage and effects

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.[4] WP

Risks and side effects

Side effects

XLR-11 has been linked to hospitalizations due to its use.[5] WP

Toxicity

XLR-11 has been linked to acute kidney injury in some users, along with AM-2201.[6][7][8] WP

Pharmacology

Detection

A forensic standard for this compound is available, and a representative mass spectrum has been posted on Forendex.[9] WP

Legal status

Legal status

XLR-11 was banned in New Zealand by being added to the temporary class drug schedule, as of 13 July 2012.[10] WP

The U.S. Drug Enforcement Administration (DEA) made XLR11 illegal under the Federal Controlled Substances act for the foreseeable future as of January 2024.[11] WP

It has also been banned in Florida as of 11 December 2012.[12] WP

Arizona banned XLR-11 on 3 April 2013.[13] WP

As of October 2015, XLR-11 is a controlled substance in China.[14] WP

XLR-11 is banned in the Czech Republic.[15] WP⚠ Part of this sentence could not be copied from the source. Open the source to read it in full.

Chemistry

Formula

C21H28FNO PC

CAS number

1364933-54-9 PC

Molar mass (g/mol)

329.5 PC

IUPAC name (computed by PubChem)

[1-(5-fluoropentyl)indol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone PC

SMILES

CC1(C(C1(C)C)C(=O)C2=CN(C3=CC=CC=C32)CCCCCF)C PC

InChIKey

PXLDPUUMIHVLEC-UHFFFAOYSA-N PC

PubChem CID

57501498

IUPAC name

(1-(5-fluoropentyl)-1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone WP

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Journal / agency Banister SD, Stuart J, Kevin RC, Edington A, Longworth M, Wilkinson SM, Beinat C, Buchanan AS, Hibbs DE, Glass M, Connor M, McGregor IS, Kassiou M. 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. August 2015. doi:10.1021/acschemneuro.5b00107 · PMID 25921407
2. Other 3-Cycloalkylcarbonyl indoles as cannabinoid receptor ligands
3. Journal / agency Frost JM, Dart MJ, Tietje KR, Garrison TR, Grayson GK, Daza AV, El-Kouhen OF, Yao BB, Hsieh GC, Pai M, Zhu CZ, Chandran P, Meyer MD. Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB(2) cannabinoid receptor activity. Journal of Medicinal Chemistry. January 2010. doi:10.1021/jm901214q · PMID 19921781
4. Journal / agency Wilkinson SM, Banister SD, Kassiou M. Bioisosteric Fluorine in the Clandestine Design of Synthetic Cannabinoids. Australian Journal of Chemistry. 2015. doi:10.1071/CH14198
5. Journal / agency Trecki J, Gerona RR, Schwartz MD. Synthetic Cannabinoid-Related Illnesses and Deaths. The New England Journal of Medicine. July 2015. doi:10.1056/NEJMp1505328 · PMID 26154784
6. Other Alphabet Soup, or the newer synthetic cannabinoids. 11 December 2013
7. Journal / agency Bhanushali GK, Jain G, Fatima H, Leisch LJ, Thornley-Brown D. AKI associated with synthetic cannabinoids: a case series. Clinical Journal of the American Society of Nephrology. April 2013. doi:10.2215/CJN.05690612 · PMID 23243266 · PMC3613952
8. Journal / agency Acute Kidney Injury Associated with Synthetic Cannabinoid Use – Multiple States, 2012. 2013-02-15
9. Other XLR-11
10. Other CB-13, MAM-2201, AKB48, and XLR11 are classified as temporary class drugs. 2012-07-05
11. Other DEA. Lists of: Scheduling Actions, Controlled Substances, Regulated Chemicals. April 2024
12. Other Attorney General Pam Bondi Outlaws Additional Synthetic Drugs. 2012-12-11
13. Other Governor Jan Brewer Signs Legislation to Combat Production, Use of Dangerous Drugs
14. Journal / agency 关于印发《非药用类麻醉药品和精神药品列管办法》的通知. 27 September 2015
15. Other Látky, o které byl doplněn seznam č. 4 psychotropních látek (příloha č. 4 k nařízení vlády č. 463/2013 Sb.)

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