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U4133

Sigma-Aldrich

URB597

≥98% (HPLC), fatty acid amide hydrolase (FAAH) inhibitor, powder

Synonym(s):

Cyclohexylcarbamic acid 3´-carbamoyl-biphenyl-3-yl ester

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About This Item

Empirical Formula (Hill Notation):
C20H22N2O3
CAS Number:
546141-08-6
Molecular Weight:
338.40
MDL number:
MFCD05863934
UNSPSC Code:
12352200
PubChem Substance ID:
329827629
NACRES:
NA.77

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Product Name

URB597, ≥98% (HPLC), powder

description

Drug Control: Új pszichoaktív anyag / New psychoactive substance (Hungary), 78/2022. (XII. 28.) BM rendelet.

Quality Level

100

assay

≥98% (HPLC)

form

powder

drug control

Új pszichoaktív anyag / New psychoactive substance (Hungary), 78/2022. (XII. 28.) BM rendelet

color

white

solubility

DMSO: soluble ~14 mg/mL

storage temp.

2-8°C

SMILES string

NC(=O)c1cccc(c1)-c2cccc(OC(=O)NC3CCCCC3)c2

InChI

1S/C20H22N2O3/c21-19(23)16-8-4-6-14(12-16)15-7-5-11-18(13-15)25-20(24)22-17-9-2-1-3-10-17/h4-8,11-13,17H,1-3,9-10H2,(H2,21,23)(H,22,24)

InChI key

ROFVXGGUISEHAM-UHFFFAOYSA-N

General description

URB597 binds to active sites of fatty acid amide hydrolases and inhibits their activity. URB597 alters expression of tyrosine hydroxylase and interacts with abnormal-cannabidiol (Abn-CBD) and peroxisome proliferator-activated receptors (PPARs). URB597 elicits antinociception property via cannabinoid receptor by maintaining endocannabinoid anandamide (AEA) levels. URB597 reduces abnormal hyperactivity in neurons and could be for treatment of seizures and improving synaptic plasticity.

Biochem/physiol Actions

Potent, selective fatty acid amide hydrolase (FAAH) inhibitor.

Preparation Note

URB597 is soluble in DMSO at a concentration that is approximately 14 mg/ml.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
025M4604V
031M4631V
129K46051
129K4605
088K46212

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Ermelinda Lomazzo et al.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology, 40(2), 488-501 (2014-08-08)
The occurrence of chronic stress, depression, and anxiety can increase nociception in humans and may facilitate the transition from localized to chronic widespread pain. The mechanisms underlying chronic widespread pain are still unknown, hindering the development of effective pharmacological therapies.
Effects of the fatty acid amide hydrolase (FAAH) inhibitor URB597 on pain-stimulated and pain-depressed behavior in rats
Kwilasz AJ, et al.
Behavioural Pharmacology, 25(2), 119-119 (2014)
Lucas Albrechet-Souza et al.
Neurobiology of stress, 15, 100387-100387 (2021-09-16)
Understanding sex differences in behavioral and molecular effects of stress has important implications for understanding the vulnerability to chronic psychiatric disorders associated with stress response circuitry. The amygdala is critical for emotional learning and generating behavioral responses to stressful stimuli
Luara A Batista et al.
Behavioural brain research, 317, 508-514 (2016-10-28)
Selective stimulation of carotid chemoreceptors by intravenous infusion of low doses of potassium cyanide (KCN) produces short-lasting escape responses that have been proposed as a model of panic attack. In turn, preclinical studies suggest that facilitation of the endocannabinoid system
The FAAH inhibitor URB597 suppresses hippocampal maximal dentate afterdischarges and restores seizure-induced impairment of short and long-term synaptic plasticity
Colangeli R, et al.
Scientific Reports, 7(1), 11152-11152 (2017)
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