UR-144
 | |
| Systematic (IUPAC) name | |
|---|---|
| (1-pentylindol-3-yl)-(2,2,3,3-tetramethylcyclopropyl)methanone | |
| Clinical data | |
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| Identifiers | |
1199943-44-6  | |
| PubChem | CID 44626619 |
| ChemSpider |
24634882 |
| ChEMBL |
CHEMBL571773 |
| Chemical data | |
| Formula | C21H29NO |
| 311.461 g/mol | |
|
SMILES
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| (what is this?) | |
UR-144 (TMCP-018, KM-X1, MN-001, YX-17) 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.
Pharmacology
UR-144 has high affinity for the CB2 receptor with a Ki of 1.8 nM but 83x lower affinity for the CB1 receptor with a Ki of 150 nM.[2] Although a later study found its CB1 affinity to be much higher than previously expected, with a Ki of 28.9nM and an EC50 of 1295nM. 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).
Legality
The UK ACMD recommended that generic prohibition legislation be extended to include UR-144 in October 2012.[3] The UK Home Office accepted the recommendation and enacted legislation to ban UR-144 as a class B drug along with a number of other drugs on February 26, 2013 as a part of The Misuse of Drugs Act 1971 (Amendment) Order 2013.
UR-144 has been detected as an ingredient of synthetic cannabis smoking blends in New Zealand, and subsequently banned from sale as a temporary class drug on 6 April 2012.[4] It has also been encountered in smoking blends and subsequently banned in Russia.[5]
Detection
A forensic standard of UR-144 is available, and the compound has been posted on the Forendex website of potential drugs of abuse.[6] An ELISA immunoassay technique for detecting UR-144 in urine as part of general drug screens has been developed by Tulip Biolabs, Inc. An Homogeneous Immunoassay that runs on most Clinical Chemistry Analyzers and detects several UR and XLR synthetic cannabinoids has been developed and introduced by Immunalysis Inc. Pomona USA.
See also
- AB-001
- AM-1221
- 4-HTMPIPO
- JTE 7-31
- JWH-018
- N-(S)-Fenchyl-1-(2-morpholinoethyl)-7-methoxyindole-3-carboxamide
- XLR-11
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, El-Kouhen OF, Yao BB, Hsieh GC, Pai M, Zhu CZ, Chandran P, Meyer MD (January 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.
- ↑ "Further consideration of the synthetic cannabinoids". UK Advisory Council on the Misuse of Drugs. 18 October 2012. p. 14. Retrieved 13 December 2014.
- ↑ Temporary Class Drug Notices. New Zealand Ministry of Health
- ↑ Sobolevsky T, Prasolov I, Rodchenkov G (October 2012). "Detection of urinary metabolites of AM-2201 and UR-144, two novel synthetic cannabinoids". Drug Test Anal 4: 745–753. doi:10.1002/dta.1418. PMID 23042760.
- ↑ Southern Association of Forensic Scientists http://forendex.southernforensic.org/index.php/detail/index/1218
Further reading
- Poso A, Huffman JW (January 2008). "Targeting the cannabinoid CB2 receptor: modelling and structural determinants of CB2 selective ligands". Br. J. Pharmacol. 153 (2): 335–46. doi:10.1038/sj.bjp.0707567. PMC 2219524. PMID 17982473.
- Chin CL, Tovcimak AE, Hradil VP, Seifert TR, Hollingsworth PR, Chandran P, Zhu CZ, Gauvin D, Pai M, Wetter J, Hsieh GC, Honore P, Frost JM, Dart MJ, Meyer MD, Yao BB, Cox BF, Fox GB (January 2008). "Differential effects of cannabinoid receptor agonists on regional brain activity using pharmacological MRI". Br. J. Pharmacol. 153 (2): 367–79. doi:10.1038/sj.bjp.0707506. PMC 2219521. PMID 17965748.
- Frost JM, Dart MJ, Tietje KR, Garrison TR, Grayson GK, Daza AV, El-Kouhen OF, Miller LN, Li L, Yao BB, Hsieh GC, Pai M, Zhu CZ, Chandran P, Meyer MD (March 2008). "Indol-3-yl-tetramethylcyclopropyl ketones: effects of indole ring substitution on CB2 cannabinoid receptor activity". J. Med. Chem. 51 (6): 1904–12. doi:10.1021/jm7011613. PMID 18311894.