UR-144

UR-144

Legal status
Legal status	Temporary Class Drug (NZ)
Identifiers
IUPAC name (1-pentylindol-3-yl)-(2,2,3,3-tetramethylcyclopropyl)methanone
CAS Number	1199943-44-6 N
PubChem CID	44626619
ChemSpider	24634882 N
ChEMBL	ChEMBL571773 N
CompTox Dashboard (EPA)	DTXSID60152635
Chemical and physical data
Formula	C21H29NO
Molar mass	311.461 g/mol g·mol−1
3D model (JSmol)	Interactive image
SMILES CCCCCN1C=C(C2=CC=CC=C21)C(=O)C3C(C3(C)C)(C)C
InChI 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
NY (what is this?)

UR-144 (TMCP-018, KM-X1, MN-001, YX-17) is a drug invented by Abbott Laboratories, 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 K_i of 1.8 nM but 83x lower affinity for the CB₁ receptor with a K_i of 150 nM. 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).

History of use

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. It has also been encountered in smoking blends and subsequently banned in Russia.

The chemical UR-144 has also been banned in the UK in 2013 along with RCS-4 and AM-2201. This is due to two people in Glasgow being admitted to hospital after taking a legal high with the chemicals in. Another person was admitted to brighton hospital after over dosing on the drug

Detection

A forensic standard of UR-144 is available, and the compound has been posted on the Forendex website of potential drugs of abuse. An ELISA immunoassay technique for detecting UR-144 in urine as part of general drug screens has been developed by Tulip Biolabs, Inc.

Beatrice smells

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

Further reading

• Poso A, Huffman JW (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. {{cite journal}}: Unknown parameter |month= ignored (help)
• 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 (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
• 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 (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)