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Chemical compound
XLR-12
Legal status
(2,2,3,3-Tetramethylcyclopropyl)[1-(4,4,4-trifluorobutyl)-1H-indol-3-yl]methanone
CAS Number
PubChem
CID
ChemSpider
UNII
Formula C 20 H 24 F 3 N O
Molar mass 351.413 g·mol−1 3D model (
JSmol )
O=C(C1C(C1(C)C)(C)C)c1cn(c2c1cccc2)CCCC(F)(F)F
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
References
^
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
^ 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 .
^
A Magyarországon megjelent, a Kábítószer és Kábítószer-függőség Európai Megfigyelő Központjának Korai Jelzőrendszerébe (EMCDDA EWS) 2005 óta bejelentett ellenőrzött anyagok büntetőjogi vonatkozású besorolása
^
"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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