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
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 GMT 2023` Edited by `admin` on `Sat Dec 16 10:25:25 GMT 2023`
Record UNII	1TYA7HVP1B
Record Status	`Validated (UNII)`
Record Version

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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