XLR-11 (drug)

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Not to be confused with Reaction Motors XLR11.
XLR-11 (drug)
XLR-11 structure.png
Systematic (IUPAC) name
(1-(5-fluoropentyl)-1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone
Clinical data
Legal status
  • US: Schedule I in Florida, Schedule 1 in South Dakota [1]
  • Temporary Class Drug (NZ)
Identifiers
CAS number 1364933-54-9 YesY
ATC code ?
ChemSpider 28537382
Chemical data
Formula C21H28FNO 
Mol. mass 329.450 g/mol

XLR-11 (5"-fluoro-UR-144) is a drug that acts as a potent agonist for the cannabinoid receptors CB1 and CB2 with a Ki of 24.2nM and a EC50 of 359nM at CB1[citation needed]. 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,[2][3] and appears to have not previously been made by Abbott Laboratories, despite falling within the claims of patent WO 2006/069196.

Detection[edit]

A forensic standard for this compound is available, and a representative mass spectrum has been posted on Forendex.[4] 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][5]

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. It was banned in New Zealand by being added to the temporary class drug schedule, effective from 13 July 2012.[6] It has also been banned in Florida as of 11 December 2012.[7] Arizona banned XLR-11 on April 3, 2013.[8]

Toxicity[edit]

XLR-11 has been linked to acute kidney injury in some users,[9] along with AM-2201.[10][11]

See also[edit]

References[edit]

  1. ^ SD HB1024
  2. ^ 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 
  3. ^ 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. 
  4. ^ "XLR-11". Structural, chemical, and analytical data on controlled substances. Southern Association of Forensic Scientists (SAFS). 
  5. ^ "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. 
  6. ^ "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. 
  7. ^ "News Release - Attorney General Pam Bondi Outlaws Additional Synthetic Drugs". News Release. State of Florida. 2012-12-11. 
  8. ^ State of Arizona, Office of the Governor. azgovernor.gov http://azgovernor.gov/dms/upload/PR_040313_SyntheticDrugs.pdf |url= missing title (help). Retrieved 2014-08-27. 
  9. ^ "Alphabet Soup, or the newer synthetic cannabinoids...". The Dose Makes The Poison Blog. 11 December 2013. Retrieved 18 September 2014. 
  10. ^ 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. 
  11. ^ "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). 2013-92-13. Retrieved 2013-02-15.