XLR-11 (drug)

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XLR-11 (drug)
Systematic (IUPAC) name
(1-(5-fluoropentyl)-1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone
Clinical data
Pregnancy cat.  ?
Legal status Schedule I in Florida (US) Temporary Class Drug (NZ)
Identifiers
CAS number 1364933-54-9 YesY
ATC code  ?
Chemical data
Formula C21H28FNO 
Mol. mass 329.450 g/mol

XLR-11 (5"-fluoro-UR-144) is a drug that presumably acts as a potent agonist for the cannabinoid receptors. 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 listed in the patent or scientific literature alongside these other similar compounds,[1][2] and appears to have not previously been made by Abbott Laboratories, despite falling within the claims of patent WO 2006/069196.

Contents

Detection [edit]

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 by "research chemical" suppliers 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.[3] It has also been banned in Florida as of 11 December 2012.[4]

Toxicity [edit]

XLR-11 has been linked to acute kidney injury in some users, along with AM-2201.[5][6]

See also [edit]

References [edit]

  1. ^ 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 
  2. ^ Frost JM, et al. (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. 
  3. ^ Temporary Class Drug Notice, 5 July 2012. NZ Department of Internal Affairs.
  4. ^ Florida Attorney General Pam Bondi Outlaws Additional Synthetic Drugs
  5. ^ Bhanushali, G. K.; Jain, G.; Fatima, H.; Leisch, L. J.; Thornley-Brown, D. (2012). "AKI Associated with Synthetic Cannabinoids: A Case Series". Clinical Journal of the American Society of Nephrology. doi:10.2215/CJN.05690612. PMID 23243266.  edit
  6. ^ "Acute Kidney Injury Associated with Synthetic Cannabinoid Use — Multiple States, 2012". US Centre for Disease Control. 15 Feb 2013. Retrieved 2013-02-15.