UR-144

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H29NO
Molecular Weight	311.4611
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCCN1C=C(C(=O)C2C(C)(C)C2(C)C)C3=CC=CC=C13

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	311.4611
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.soft-tox.org/files/designer_drugs/UR-144.pdf
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cannabinoid CB2 receptor 71 Target ID: CHEMBL253 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19921781 \| http://www.soft-tox.org/files/designer_drugs/UR-144.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/25921407	Agonist 2678		29.0 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614 Sources: http://www.soft-tox.org/files/designer_drugs/UR-144.pdf http://www.who.int/medicines/areas/quality_safety/4_8_Review.pdf	Palliative		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Inhibitory effect of synthetic cannabinoids on CYP1A activity in mouse liver microsomes.	2014	25374372
Genotoxic properties of representatives of alkylindazoles and aminoalkyl-indoles which are consumed as synthetic cannabinoids.	2015 Jun	25792264

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

UR-144 preferentially binds the peripheral CB2 receptor with Ki = 1.8 nM.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 10:25:25 UTC 2023` Edited by `admin` on `Sat Dec 16 10:25:25 UTC 2023`
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