XLR-12

Chemical compound
Identifiers
  • (2,2,3,3-Tetramethylcyclopropyl)[1-(4,4,4-trifluorobutyl)-1H-indol-3-yl]methanone
CAS Number
  • 895155-78-9 checkY
PubChem CID
  • 11559386
ChemSpider
  • 9734160
UNII
  • EG79K9XQF5
CompTox Dashboard (EPA)
  • DTXSID201024738 Edit this at Wikidata
Chemical and physical dataFormulaC20H24F3NOMolar mass351.413 g·mol−13D model (JSmol)
  • Interactive image
  • O=C(C1C(C1(C)C)(C)C)c1cn(c2c1cccc2)CCCC(F)(F)F
InChI
  • InChI=1S/C20H24F3NO/c1-18(2)17(19(18,3)4)16(25)14-12-24(11-7-10-20(21,22)23)15-9-6-5-8-13(14)15/h5-6,8-9,12,17H,7,10-11H2,1-4H3
  • Key:PEXYKZYTXIEEOB-UHFFFAOYSA-N

XLR-12 is an indole-based synthetic cannabinoid drug that was invented by Abbott Laboratories in 2006.[1] It is an analogue of XLR-11 where the 5-fluoropentyl chain has been replaced with a 4,4,4-trifluorobutyl chain. XLR-12 is relatively highly selective for the CB2 receptor, with a Ki of 0.09 nM and 167x selectivity over the related CB1 receptor, however it still retains appreciable affinity for CB1 with a Ki of 15 nM.[2]

Legal status

XLR-12 is illegal in Hungary[3] and Japan.[4]

See also

  • UR-144
  • FUB-144
  • JTE 7-31

References

  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, Dart MJ, Tietje KR, Garrison TR, Grayson GK, Daza AV, et al. (January 2010). "Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB(2) cannabinoid receptor activity". Journal of Medicinal Chemistry. 53 (1): 295–315. doi:10.1021/jm901214q. PMID 19921781.
  3. ^ A Magyarországon megjelent, a Kábítószer és Kábítószer-függőség Európai Megfigyelő Központjának Korai Jelzőrendszerébe (EMCDDA EWS) 2005 óta bejelentett ellenőrzött anyagok büntetőjogi vonatkozású besorolása
  4. ^ "指定薬物名称・構造式一覧（平成27年9月16日現在）" (PDF) (in Japanese). 厚生労働省. 16 September 2015. Retrieved 8 October 2015.
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