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'''(1-Pentylindol-3-yl)-(2,2,3,3-tetramethylcyclopropyl)methanone''' ('''KM X-1''', '''UR-144''') is a drug invented by [[Abbott Laboratories]],<ref name = "WO2006/069196">{{ cite patent | country = WO | number = 2006069196 | status = application | title = 3-Cycloalkylcarbonyl indoles as cannabinoid receptor ligands | pubdate = 2006-06-29 | fdate = | pridate = | inventor = Pace JM, Tietje K, Dart MJ, Meyer MD | assign1 = Abbott s*ck my di*k Laboratories }}</ref> that acts as a selective [[full agonist]] of the peripheral [[cannabinoid receptor]] [[Cannabinoid receptor 2|CB<sub>2</sub>]], but with much lower affinity for the psychoactive [[Cannabinoid receptor 1|CB<sub>1</sub>]] receptor. It has high affinity for the CB<sub>2</sub> receptor with a K<sub>i</sub> of 1.8nM but 83x lower affinity for the CB<sub>1</sub> receptor with a K<sub>i</sub> of 150nM.<ref name="pmid19921781">{{cite journal | author = 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 | title = Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB(2) cannabinoid receptor activity | journal = J. Med. Chem. | volume = 53 | issue = 1 | pages = 295–315 | year = 2010 | month = January | pmid = 19921781 | doi = 10.1021/jm901214q }}</ref> Chemically it is closely related to other 2,2,3,3-tetramethylcyclopropyl synthetic cannabinoids like [[A-796,260]] and [[A-834,735]] but with a different substitution on the 1-position of the indole core, in these compounds its 1-pentyl group is replaced with alkylheterocycles like 1-(2-morpholinoethyl) and 1-(tetrahydropyran-4-ylmethyl).
'''(1-Pentylindol-3-yl)-(2,2,3,3-tetramethylcyclopropyl)methanone''' ('''KM X-1''', '''UR-144''') is a drug invented by [[Abbott Laboratories]],<ref name = "WO2006/069196">{{ cite patent | country = WO | number = 2006069196 | status = application | title = 3-Cycloalkylcarbonyl indoles as cannabinoid receptor ligands | pubdate = 2006-06-29 | fdate = | pridate = | inventor = Pace JM, Tietje K, Dart MJ, Meyer MD | assign1 = Abbott Laboratories }}</ref> that acts as a selective [[full agonist]] of the peripheral [[cannabinoid receptor]] [[Cannabinoid receptor 2|CB<sub>2</sub>]], but with much lower affinity for the psychoactive [[Cannabinoid receptor 1|CB<sub>1</sub>]] receptor. It has high affinity for the CB<sub>2</sub> receptor with a K<sub>i</sub> of 1.8nM but 83x lower affinity for the CB<sub>1</sub> receptor with a K<sub>i</sub> of 150nM.<ref name="pmid19921781">{{cite journal | author = 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 | title = Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB(2) cannabinoid receptor activity | journal = J. Med. Chem. | volume = 53 | issue = 1 | pages = 295–315 | year = 2010 | month = January | pmid = 19921781 | doi = 10.1021/jm901214q }}</ref> Chemically it is closely related to other 2,2,3,3-tetramethylcyclopropyl synthetic cannabinoids like [[A-796,260]] and [[A-834,735]] but with a different substitution on the 1-position of the indole core, in these compounds its 1-pentyl group is replaced with alkylheterocycles like 1-(2-morpholinoethyl) and 1-(tetrahydropyran-4-ylmethyl).


==See also==
==See also==

Revision as of 00:04, 20 May 2012

UR-144
Legal status
Legal status
  • Temporary Class Drug (NZ)
Identifiers
  • (1-pentylindol-3-yl)-(2,2,3,3-tetramethylcyclopropyl)methanone
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H29NO
Molar mass311.461 g/mol g·mol−1
3D model (JSmol)
  • CCCCCN1C=C(C2=CC=CC=C21)C(=O)C3C(C3(C)C)(C)C
  • InChI=1S/C21H29NO/c1-6-7-10-13-22-14-16(15-11-8-9-12-17(15)22)18(23)19-20(2,3)21(19,4)5/h8-9,11-12,14,19H,6-7,10,13H2,1-5H3 ☒N
  • Key:NBMMIBNZVQFQEO-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)

(1-Pentylindol-3-yl)-(2,2,3,3-tetramethylcyclopropyl)methanone (KM X-1, UR-144) is a drug invented by Abbott Laboratories,[1] that acts as a selective full agonist of the peripheral cannabinoid receptor CB2, but with much lower affinity for the psychoactive CB1 receptor. It has high affinity for the CB2 receptor with a Ki of 1.8nM but 83x lower affinity for the CB1 receptor with a Ki of 150nM.[2] Chemically it is closely related to other 2,2,3,3-tetramethylcyclopropyl synthetic cannabinoids like A-796,260 and A-834,735 but with a different substitution on the 1-position of the indole core, in these compounds its 1-pentyl group is replaced with alkylheterocycles like 1-(2-morpholinoethyl) and 1-(tetrahydropyran-4-ylmethyl).

See also

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, El-Kouhen OF, Yao BB, Hsieh GC, Pai M, Zhu CZ, Chandran P, Meyer MD (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)

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