XLR-12

XLR-12

Legal status
Legal status	CA: Schedule II
Identifiers
IUPAC name (2,2,3,3-Tetramethylcyclopropyl)[1-(4,4,4-trifluorobutyl)-1H-indol-3-yl]methanone
CAS Number	895155-78-9
PubChem (CID)	11559386
ChemSpider	9734160
Chemical and physical data
Formula	C20H24F3NO
Molar mass	351.405 g/mol
3D model (Jmol)	Interactive image
SMILES 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 K_i of 0.09 nM and 167x selectivity over the related CB₁ receptor, however it still retains appreciable affinity for CB₁ with a K_i 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, J. M.; et al. (2010). "Indol-3-ylcycloalkyl Ketones: Effects of N1 Substituted Indole Side Chain Variations on CB2 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.