Cannabis Ruderalis

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Importing Wikidata short description: "Chemical compound" (Shortdesc helper)
 
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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| IUPAC_name = (2,2,3,3-Tetramethylcyclopropyl)[1-(4,4,4-trifluorobutyl)-1H-indol-3-yl]methanone
| IUPAC_name = (2,2,3,3-Tetramethylcyclopropyl)[1-(4,4,4-trifluorobutyl)-1H-indol-3-yl]methanone
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<!--Identifiers-->
<!--Identifiers-->
| CAS_number_Ref =
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 895155-78-9
| CAS_number = 895155-78-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = EG79K9XQF5
| ATC_prefix =
| ATC_prefix =
| ATC_suffix =
| ATC_suffix =
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<!--Chemical data-->
<!--Chemical data-->
| C=20 | H=24 | F=3 | N=1 | O=1
| C=20 | H=24 | F=3 | N=1 | O=1
| molecular_weight = 351.405 g/mol
}}
}}


'''XLR-12''' is an [[indole]]-based [[synthetic cannabinoid]] drug that was invented by [[Abbott Laboratories]] in 2006.<ref name = "WO2006/069196">{{cite patent |country= WO |number= 2006069196 |status= application |title= 3-Cycloalkylcarbonyl indoles as cannabinoid receptor ligands |pubdate= 2006-06-29 |inventor= Pace JM, Tietje K, Dart MJ, Meyer MD |assign1= Abbott Laboratories }}</ref> It is an analogue of [[XLR-11 (drug)|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 CB<sub>2</sub> receptor, with a K<sub>i</sub> of 0.09 nM and 167x selectivity over the related CB<sub>1</sub> receptor, however it still retains appreciable affinity for CB<sub>1</sub> with a K<sub>i</sub> of 15 nM.<ref>{{Cite journal |last1= Frost |first1= J. M.|doi= 10.1021/jm901214q |title= Indol-3-ylcycloalkyl Ketones: Effects of N1 Substituted Indole Side Chain Variations on CB2 Cannabinoid Receptor Activity |journal= Journal of Medicinal Chemistry |volume= 53 |issue= 1 |pages= 295–315 |year= 2010 |pmid= 19921781 |display-authors=etal}}</ref>
'''XLR-12''' is an [[indole]]-based [[synthetic cannabinoid]] drug that was invented by [[Abbott Laboratories]] in 2006.<ref name = "WO2006/069196">{{cite patent |country= WO |number= 2006069196 |status= application |title= 3-Cycloalkylcarbonyl indoles as cannabinoid receptor ligands |pubdate= 2006-06-29 |inventor= Pace JM, Tietje K, Dart MJ, Meyer MD |assign1= Abbott Laboratories }}</ref> It is an analogue of [[XLR-11 (drug)|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 CB<sub>2</sub> receptor, with a K<sub>i</sub> of 0.09 nM and 167x selectivity over the related CB<sub>1</sub> receptor, however it still retains appreciable affinity for CB<sub>1</sub> with a K<sub>i</sub> of 15 nM.<ref>{{cite journal | vauthors = 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 | display-authors = 6 | title = Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB(2) cannabinoid receptor activity | journal = Journal of Medicinal Chemistry | volume = 53 | issue = 1 | pages = 295–315 | date = January 2010 | pmid = 19921781 | doi = 10.1021/jm901214q }}</ref>


== Legal status ==
== Legal status ==
XLR-12 is illegal in Hungary<ref>[http://www.daath.hu/incoming/designer_jogi_lista_20150903_BSZKI_Daath_kieg.pdf A Magyarországon megjelent, a Kábítószer és Kábítószer-függőség Európai Megfigyelő Központjának Korai Jelzőrendszerébe (EMCDDA EWS) 2005 óta bejelentett ellenőrzött anyagok büntetőjogi vonatkozású besorolása]</ref> and Japan.<ref>{{cite web | url=http://www.mhlw.go.jp/seisakunitsuite/bunya/kenkou_iryou/iyakuhin/yakubuturanyou/dl/meisho.pdf | title=指定薬物名称・構造式一覧（平成27年9月16日現在） | publisher=厚生労働省 | date=16 September 2015 | language=Japanese | accessdate=8 October 2015}}</ref>
XLR-12 is illegal in Hungary<ref>[http://www.daath.hu/incoming/designer_jogi_lista_20150903_BSZKI_Daath_kieg.pdf A Magyarországon megjelent, a Kábítószer és Kábítószer-függőség Európai Megfigyelő Központjának Korai Jelzőrendszerébe (EMCDDA EWS) 2005 óta bejelentett ellenőrzött anyagok büntetőjogi vonatkozású besorolása]</ref> and Japan.<ref>{{cite web | url=http://www.mhlw.go.jp/seisakunitsuite/bunya/kenkou_iryou/iyakuhin/yakubuturanyou/dl/meisho.pdf | title=指定薬物名称・構造式一覧（平成27年9月16日現在） | publisher=厚生労働省 | date=16 September 2015 | language=Japanese | access-date=8 October 2015}}</ref>


==See also==
== See also ==
* [[UR-144]]
* [[UR-144]]
* [[FUB-144]]
* [[FUB-144]]
* [[JTE 7-31]]
* [[JTE 7-31]]


==References==
== References ==
{{reflist}}
{{reflist}}


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[[Category:Cannabinoids]]
[[Category:Cannabinoids]]
[[Category:Designer drugs]]
[[Category:Designer drugs]]
[[Category:Indoles]]
[[Category:Tetramethylcyclopropanoylindoles]]
[[Category:Tetramethylcyclopropanoylindoles]]



{{cannabinoid-stub}}
{{cannabinoid-stub}}

Latest revision as of 03:56, 13 April 2022

XLR-12
Legal status
Legal status
Identifiers
  • (2,2,3,3-Tetramethylcyclopropyl)[1-(4,4,4-trifluorobutyl)-1H-indol-3-yl]methanone
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC20H24F3NO
Molar mass351.413 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[edit]

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

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, 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.
source: https://en.wikipedia.org/w/index.php?title=XLR-12&diff=1082426990&oldid=722651682

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