|Systematic (IUPAC) name|
|CAS Registry Number|
|Molecular mass||329.46 g·mol−1|
XLR-11 (5"-fluoro-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.
A forensic standard for this compound is available, and a representative mass spectrum has been posted on Forendex. An ELISA immunoassay technique for detecting XLR-11 and UR-144 in blood and urine as part of general drug screens has been developed by Randox Laboratories and Tulip Biolabs, Inc.
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. It was banned in New Zealand by being added to the temporary class drug schedule, effective from 13 July 2012. It has also been banned in Florida as of 11 December 2012. Arizona banned XLR-11 on April 3, 2013.
- SD HB1024
- Banister, S. D.; Stuart, J.; Kevin, R. C.; Edington, A.; Longworth, M.; Wilkinson, S. M.; Beinat, C.; Buchanan, A. S.; Hibbs, D. E.; Glass, M.; Connor, M.; McGregor, I. S.; Kassiou, M. (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: 150508124201002. doi:10.1021/acschemneuro.5b00107.
- 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
- 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 (January 2010). "Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB(2) cannabinoid receptor activity". J. Med. Chem. 53 (1): 295–315. doi:10.1021/jm901214q. PMID 19921781.
- "XLR-11". Structural, chemical, and analytical data on controlled substances. Southern Association of Forensic Scientists (SAFS).
- "Randox Toxicology launches ELISA for the detection of new generation Synthetic Cannabinoids (Spice) drugs UR-144 and XLR-11". Press Release. Randox Laboratories Ltd. 2013-04-29.
- Wilkinson, S. M.; Banister, S. D.; Kassiou, M. (2015). "Bioisosteric Fluorine in the Clandestine Design of Synthetic Cannabinoids". Australian Journal of Chemistry 68: 4. 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. 2012-07-05.
- "Attorney General Pam Bondi Outlaws Additional Synthetic Drugs" (Press release). State of Florida. 2012-12-11.
- "Governor Jan Brewer Signs Legislation to Combat Production, Use of Dangerous Drugs" (PDF) (Press release). Office of the Governor, State of Arizona. Retrieved 2014-08-27.
- "Alphabet Soup, or the newer synthetic cannabinoids...". The Dose Makes The Poison Blog. 11 December 2013. Retrieved 18 September 2014.
- Bhanushali GK, Jain G, Fatima H, Leisch LJ, Thornley-Brown D (April 2013). "AKI associated with synthetic cannabinoids: a case series". Clin J Am Soc Nephrol 8 (4): 523–6. doi:10.2215/CJN.05690612. 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). 2013-02-15. Retrieved 2013-02-15.
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