U4133

URB597

Name: URB597
Brand: SIGMA

≥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

UNSPSC Code:

12352200

PubChem Substance ID:

329827629

NACRES:

NA.77

MDL number:

MFCD05863934

Product Name

URB597, ≥98% (HPLC), powder

SMILES string

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

InChI key

ROFVXGGUISEHAM-UHFFFAOYSA-N

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)

description

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

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

Quality Level

100

Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

Biochem/physiol Actions

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

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.

Preparation Note

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

Eyeshields, Gloves

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The FAAH inhibitor URB597 efficiently reduces tyrosine hydroxylase expression through CB1-and FAAH-independent mechanisms

Bosier B, et al.

British Journal of Pharmacology, 169(4), 794-807 (2013)

Mechanism of carbamate inactivation of FAAH: implications for the design of covalent inhibitors and in vivo functional probes for enzymes

Alexander JP and Cravatt BF

Chemistry & Biology, 12(11), 1179-1187 (2005)

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)

Interaction between the cholecystokinin and endogenous cannabinoid systems in cued fear expression and extinction retention

Bowers ME and Ressler KJ

Neuropsychopharmacology, 30, 688-688 (2015)

Amygdalar endocannabinoids are affected by predator odor stress in a sex-specific manner and modulate acoustic startle reactivity in female rats.

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

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