XLR-11 (drug)

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Not to be confused with Reaction Motors XLR11.
XLR-11
XLR-11 structure.png
Systematic (IUPAC) name
(1-(5-fluoropentyl)-1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone
Clinical data
Legal status
  • NZ: Temporary Class Drug
  • US: Schedule I in Florida, Schedule 1 in South Dakota[1]
Identifiers
CAS Registry Number 1364933-54-9 YesY
ChemSpider 28537382
Chemical data
Formula C21H28FNO
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.[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[edit]

A forensic standard for this compound is available, and a representative mass spectrum has been posted on Forendex.[5] 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.[1][6]

Recreational use[edit]

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.[7] It was banned in New Zealand by being added to the temporary class drug schedule, effective from 13 July 2012.[8] It has also been banned in Florida as of 11 December 2012.[9] Arizona banned XLR-11 on April 3, 2013.[10]

Toxicity[edit]

XLR-11 has been linked to acute kidney injury in some users,[11] along with AM-2201.[12][13]

See also[edit]

References[edit]

  1. ^ SD HB1024
  2. ^ a b 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.  edit
  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, 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. 
  5. ^ "XLR-11". Structural, chemical, and analytical data on controlled substances. Southern Association of Forensic Scientists (SAFS). 
  6. ^ "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. 
  7. ^ 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.  edit
  8. ^ "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. 
  9. ^ "Attorney General Pam Bondi Outlaws Additional Synthetic Drugs" (Press release). State of Florida. 2012-12-11. 
  10. ^ "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. 
  11. ^ "Alphabet Soup, or the newer synthetic cannabinoids...". The Dose Makes The Poison Blog. 11 December 2013. Retrieved 18 September 2014. 
  12. ^ 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. 
  13. ^ "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.