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U3010

Sigma-Aldrich

URB602

≥98% (HPLC)

Synonym(s):

[1,1’-Biphenyl]-3-yl-carbamic acid cyclohexyl ester

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About This Item

Empirical Formula (Hill Notation):
C19H21NO2
CAS Number:
565460-15-3
Molecular Weight:
295.38
MDL number:
MFCD08457914
UNSPSC Code:
12352200
PubChem Substance ID:
329827625

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to off-white

solubility

DMSO: >10 mg/mL

storage temp.

2-8°C

SMILES string

O=C(Nc1cccc(c1)-c2ccccc2)OC3CCCCC3

InChI

1S/C19H21NO2/c21-19(22-18-12-5-2-6-13-18)20-17-11-7-10-16(14-17)15-8-3-1-4-9-15/h1,3-4,7-11,14,18H,2,5-6,12-13H2,(H,20,21)

InChI key

HHVUFQYJOSFTEH-UHFFFAOYSA-N

Biochem/physiol Actions

URB602 is an inhibitor of monoacylglycerol lipase (MGL). The IC50 = 28 μM and Km = 20 μM. URB602 increases 2-arachidonoylglycerol (2-AG) concentrations. When URB602 is injected into the periaqueductal grey matter, it enhances stress-induced analgesia (tail-flick test) in a CB1-dependent manner. An effect that is prevented by a CB1 cannabinoid receptor antagonist, Rimonabant (SR141716). URB602 is not suitable for systemic administration due to relatively low potency, but useful for research of pain and stress-related disorders, which identifies MGL as a previously unrecognized therapeutic target (highlighted in Chemical Engineering News, June 27, 2005).

Preparation Note

URB602 is soluble in DMSO at a concentration >10 mg/ml.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Renyan Liu et al.
Cell death and differentiation, 27(10), 2888-2903 (2020-05-08)
We have previously reported that Monoglyceride Lipase (MGL) expression is absent or reduced in various human malignancies and MGL-deficient mice develop tumors in multiple organs. Evidence also suggests MGL to be a tumor suppressor, however, the mechanisms underlying its tumor-suppressive
Kerong Hai et al.
Critical care medicine, 47(2), e144-e151 (2018-11-16)
Monoacylglycerol lipase participates in organ protection by regulating the hydrolysis of the endocannabinoid 2-arachidonoylglycerol. This study investigated whether blocking monoacylglycerol lipase protects against postresuscitation myocardial injury and improves survival in a rat model of cardiac arrest and cardiopulmonary resuscitation. Prospective
Gero Steinberg
PloS one, 7(5), e38181-e38181 (2012-06-06)
The Transfersome® is a lipid vesicle that contains membrane softeners, such as Tween 80, to make it ultra-deformable. This feature makes the Transfersome® an efficient carrier for delivery of therapeutic drugs across the skin barrier. It was reported that TDT
Francisco J Pavon et al.
Alcoholism, clinical and experimental research, 44(11), 2158-2165 (2020-09-19)
Ethanol (EtOH) self-administration is particularly sensitive to the modulation of CB1 signaling in the nucleus accumbens (NAc) shell, and EtOH consumption increases extracellular levels of the endogenous cannabinoid CB1 receptor agonist 2-arachidonoyl glycerol (2-AG) in this brain region. Stimulation of
Michiel G J Balvers et al.
Metabolomics : Official journal of the Metabolomic Society, 8(6), 1130-1147 (2012-11-09)
It is well established that dietary intake of n-3 fatty acids is associated with anti-inflammatory effects, and this has been linked to modulation of the oxylipin and endocannabinoid metabolomes. However, the amount of data on specific tissue effects is limited
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