U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C21H29NO2
Molecular Weight 327.4605
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of UR-144 N(4-HYDROXYPENTYL)

SMILES

CC(O)CCCN1C=C(C(=O)C2C(C)(C)C2(C)C)C3=CC=CC=C13

InChI

InChIKey=YHFHYHZNLCEAAP-UHFFFAOYSA-N
InChI=1S/C21H29NO2/c1-14(23)9-8-12-22-13-16(15-10-6-7-11-17(15)22)18(24)19-20(2,3)21(19,4)5/h6-7,10-11,13-14,19,23H,8-9,12H2,1-5H3

HIDE SMILES / InChI

Molecular Formula C21H29NO2
Molecular Weight 327.4605
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/24812645 | https://www.ncbi.nlm.nih.gov/pubmed/26792810 | https://www.ncbi.nlm.nih.gov/pubmed/26514671

UR-144 N(4-hydroxypentyl) is a potent synthetic cannabinoid designed by Abbott Laboratories as a CB2 selective agonist for pain management. UR-144 N(4-hydroxypentyl) is a metabolite of another CB2-selective cannabinoid UR-144. Pre-clinical studies of nociceptive and neuropathic pain have shown that CB2-selective ligands are analgesics without causing the adverse side effects linked with CB1 receptor activation. However, nor UR-144 nor UR-144 N(4-hydroxypentyl) has no therapeutic application.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Quantitative measurement of XLR11 and UR-144 in oral fluid by LC-MS-MS.
2014 Jul-Aug
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
Phoenix Amphotropic (AMPHO) cell line were washed twice with Opti-MEM I Reduced Serum Medium to remove any remaining FBS, and 100 μL of Opti-MEM I was added. The Nano-Glo Live Cell reagent (Promega), a nonlytic detection reagent containing the cell permeable furimazine substrate, was prepared by diluting the Nano-Glo Live Cell substrate 20× using Nano-Glo LCS Dilution buffer, and 25 μL was added to each well. Subsequently, the plate was placed in a luminometer, the GloMAX96 (Promega). Luminescence was monitored during the equilibration period until the signal stabilized (30−45 min). For agonist experiments, we added 10 μL per well of test compounds (UR-144 N-pentanoic acid), present as 13.5× stocks in 50% methanol in Opti-MEM I. The luminescence was continuously detected for 120 min. Solvent controls were run in all experiments; the final concentration of methanol (3.7%) did not pose a problem given the short readout time of the assay.
Substance Class Chemical
Created
by admin
on Sat Dec 16 11:20:11 UTC 2023
Edited
by admin
on Sat Dec 16 11:20:11 UTC 2023
Record UNII
HOM2IB42C4
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
UR-144 N(4-HYDROXYPENTYL)
Common Name English
UR-144 N-(4-HYDROXYPENTYL)METABOLITE
Common Name English
METHANONE, (1-(4-HYDROXYPENTYL)-1H-INDOL-3-YL)(2,2,3,3-TETRAMETHYLCYCLOPROPYL)-
Systematic Name English
4-HYDROXY-UR-144
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID801043116
Created by admin on Sat Dec 16 11:20:11 UTC 2023 , Edited by admin on Sat Dec 16 11:20:11 UTC 2023
PRIMARY
PUBCHEM
91736656
Created by admin on Sat Dec 16 11:20:11 UTC 2023 , Edited by admin on Sat Dec 16 11:20:11 UTC 2023
PRIMARY
FDA UNII
HOM2IB42C4
Created by admin on Sat Dec 16 11:20:11 UTC 2023 , Edited by admin on Sat Dec 16 11:20:11 UTC 2023
PRIMARY
CAS
1537889-04-5
Created by admin on Sat Dec 16 11:20:11 UTC 2023 , Edited by admin on Sat Dec 16 11:20:11 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> METABOLITE
22 ng/mL (serum, ER arrival); 10 ng/mL (serum, 10h after ER arrival)
IN-VIVO
Scientific Literature