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Details

Stereochemistry ACHIRAL
Molecular Formula C21H29NO2
Molecular Weight 327.4612
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of UR-144 N-5-HYDROXYPENTYL

SMILES

CC1(C)C(C(=O)c2cn(CCCCCO)c3ccccc23)C1(C)C

InChI

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

HIDE SMILES / InChI

Molecular Formula C21H29NO2
Molecular Weight 327.4612
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: The description was created based on several sources, including https://encrypted.google.com/patents/WO2006069196A1 | https://www.ncbi.nlm.nih.gov/pubmed/24014837

UR-144 N-5-Hydroxypentyl is a potent synthetic cannabinoid designed by Abbott Laboratories as a CB2 selective agonist for pain management. UR-144 N-5-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-5-Hydroxypentyl has no therapeutic application.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
9.15 null [pKi]
6.17 null [pKi]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB(2) cannabinoid receptor activity.
2010 Jan 14
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
FLIPR assays were performed using HEK cells stably coexpressing the chimeric GRq/o5 protein with the human CB2 receptor. Cells were seeded at 75 000 cells per well 1 day prior to the assay and assays performed with no-wash dye (FLIPR calcium assay kit, Molecular Devices, Sunnyvale, CA). Variable concentrations of compound 51 (UR-144 N-5-Hydroxypentyl) (0.3 nM to 10 μM), CP-55,940 (4) (at 10 μM final concentration) positive control, or vehicle negative control were added to cells in the presence of assay buffer (10 mM HEPES, pH 7.4, 130 mM NaCl, 5 mM KCl, 0.05% BSA), and fluorescence responses were measured immediately with a FLIPR machine. Net peak responses were compared with that of 10 μM CP-55,940 (4) and expressed as percentages of the CP-55,940 (4) evoked response.
Substance Class Chemical
Created
by admin
on Sat Jun 26 16:32:26 UTC 2021
Edited
by admin
on Sat Jun 26 16:32:26 UTC 2021
Record UNII
4MC625LVID
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
UR-144 N-5-HYDROXYPENTYL
Common Name English
UR-144 N-(5-HYDROXYPENTYL)METABOLITE
Common Name English
5-HYDROXY-UR-144
Common Name English
METHANONE, (1-(5-HYDROXYPENTYL)-1H-INDOL-3-YL)(2,2,3,3-TETRAMETHYLCYCLOPROPYL)-
Systematic Name English
Code System Code Type Description
CAS
895155-95-0
Created by admin on Sat Jun 26 16:32:27 UTC 2021 , Edited by admin on Sat Jun 26 16:32:27 UTC 2021
PRIMARY
FDA UNII
4MC625LVID
Created by admin on Sat Jun 26 16:32:27 UTC 2021 , Edited by admin on Sat Jun 26 16:32:27 UTC 2021
PRIMARY
PUBCHEM
11515395
Created by admin on Sat Jun 26 16:32:27 UTC 2021 , Edited by admin on Sat Jun 26 16:32:27 UTC 2021
PRIMARY
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Agonist of Human cannabinoid 1 & 2 receptors (CB1, CB2); Ki=680 nM (CB1), 0.71 nM(CB2)
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