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Details

Stereochemistry ACHIRAL
Molecular Formula C21H29NO
Molecular Weight 311.4618
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of UR-144

SMILES

CCCCCn1cc(c2ccccc21)C(=O)C3C(C)(C)C3(C)C

InChI

InChIKey=NBMMIBNZVQFQEO-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C21H29NO
Molecular Weight 311.4618
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: Description was created based on several sources, including http://www.who.int/medicines/areas/quality_safety/4_8_Review.pdf

UR-144 is a potent synthetic cannabinoid designed by Abbott Laboratories as a CB2 selective agonist for pain management and other indications. UR-144 preferentially binds the peripheral CB2 receptor (Ki = 1.8 nM) over the central CB1 receptor (Ki = 150 nM). 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, UR-144 has no therapeutic application. According to the FDA (US Food and Drug Administration) there are currently no approved or on-going drug applications for the medical use of UR-144.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Inhibitory effect of synthetic cannabinoids on CYP1A activity in mouse liver microsomes.
2014
Genotoxic properties of representatives of alkylindazoles and aminoalkyl-indoles which are consumed as synthetic cannabinoids.
2015 Jun
Patents

Patents

Sample Use Guides

UR-144 (10 and 30 mg/kg) depressed the locomotor activity in mice in a time and dose-dependent manner and with an ID50-value of 7.8 mg/kg
Route of Administration: Unknown
UR-144 preferentially binds the peripheral CB2 receptor with Ki = 1.8 nM.
Substance Class Chemical
Created
by admin
on Sat Jun 26 07:38:46 UTC 2021
Edited
by admin
on Sat Jun 26 07:38:46 UTC 2021
Record UNII
1TYA7HVP1B
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
UR-144
Code English
2,2,3,3-TETRAMETHYLCYCLOPROPYL(1-PENTYL-1H-INDOLE-3-YL) KETONE
Systematic Name English
(1-PENTYL-1H-INDOL-3-YL)(2,2,3,3-TETRAMETHYLCYCLOPROPYL)METHANONE
Systematic Name English
J3.184.806G
Code English
TMCP-018
Code English
YX-17
Code English
KM-X1
Code English
DEA NO. 7144
Code English
METHANONE, (1-PENTYL-1H-INDOL-3-YL)(2,2,3,3-TETRAMETHYLCYCLOPROPYL)-
Systematic Name English
Classification Tree Code System Code
DEA NO. 7144
Created by admin on Sat Jun 26 07:38:46 UTC 2021 , Edited by admin on Sat Jun 26 07:38:46 UTC 2021
Code System Code Type Description
CAS
1199943-44-6
Created by admin on Sat Jun 26 07:38:46 UTC 2021 , Edited by admin on Sat Jun 26 07:38:46 UTC 2021
PRIMARY
WIKIPEDIA
UR-144
Created by admin on Sat Jun 26 07:38:46 UTC 2021 , Edited by admin on Sat Jun 26 07:38:46 UTC 2021
PRIMARY
FDA UNII
1TYA7HVP1B
Created by admin on Sat Jun 26 07:38:46 UTC 2021 , Edited by admin on Sat Jun 26 07:38:46 UTC 2021
PRIMARY
PUBCHEM
44626619
Created by admin on Sat Jun 26 07:38:46 UTC 2021 , Edited by admin on Sat Jun 26 07:38:46 UTC 2021
PRIMARY
EPA CompTox
1199943-44-6
Created by admin on Sat Jun 26 07:38:46 UTC 2021 , Edited by admin on Sat Jun 26 07:38:46 UTC 2021
PRIMARY
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METABOLITE -> PARENT
22 ng/mL (serum, ER arrival); 10 ng/mL (serum, 10h after ER arrival)
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ACTIVE MOIETY
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