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SML1899

SR144528

Name: SR144528
Brand: SIGMA

≥98% (HPLC), CB2 receptor inverse agonist, powder

Synonym(s):

5-(4-Chloro-3-methylphenyl)-1-[(4-methylphenyl)methyl]-N-[(1S,2S,4R)-1,3,3-trimethylbicyclo[2.2.1]hept-2-yl]-1H-pyrazole-3-carboxamide, SR-144528

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About This Item

Empirical Formula (Hill Notation):

C₂₉H₃₄ClN₃O

CAS Number:

192703-06-3

Molecular Weight:

476.05

NACRES:

NA.77

UNSPSC Code:

12352200

MDL number:

MFCD05662316

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

100

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Properties

Product Name

SR144528, ≥98% (HPLC)

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 10 mg/mL, clear

storage temp.

−20°C

SMILES string

C[C@]12[C@H](NC(C3=NN(CC4=CC=C(C)C=C4)C(C5=CC=C(Cl)C(C)=C5)=C3)=O)C(C)(C)[C@@H](C2)CC1

InChI

1S/C29H34ClN3O/c1-18-6-8-20(9-7-18)17-33-25(21-10-11-23(30)19(2)14-21)15-24(32-33)26(34)31-27-28(3,4)22-12-13-29(27,5)16-22/h6-11,14-15,22,27H,12-13,16-17H2,1-5H3,(H,31,34)/t22-,27-,29+/m1/s1

InChI key

SUGVYNSRNKFXQM-XRHWURSXSA-N

Description

Application

SR144528 has been used as a cannabinoid CB2 receptor antagonist:

to study its blocking effect on the anti-dyskinetic functionality of HU-308
to study its effects on spontaneous excitatory postsynaptic currents (sEPSCs) from the globus pallidus neurons
to analyze its effect on the gastric emptying in rats

Biochem/physiol Actions

SR144528 is a potent and highly selective cannabinoid CB2 receptor inverse agonist.

SR144528 is a potent and highly selective cannabinoid CB2 receptor inverse agonist. SR144528 exhibited a Ki of 0.6 nM at CB2 compared to 400 nM at the related CB1 receptor.

Storage Class

11 - Combustible Solids

wgk

WGK 3

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Cannabinoids depress excitatory neurotransmission between the subthalamic nucleus and the globus pallidus.

I Freiman et al.

Neuroscience, 133(1), 305-313 (2005-05-17)

The globus pallidus receives its major glutamatergic input from the subthalamic nucleus and subthalamic nucleus neurons synthesize CB1 cannabinoid receptors. The hypothesis of the present work was that CB1 receptors are localized in terminals of subthalamo-pallidal glutamatergic axons and that

SR 144528, the first potent and selective antagonist of the CB2 cannabinoid receptor.

M Rinaldi-Carmona et al.

The Journal of pharmacology and experimental therapeutics, 284(2), 644-650 (1998-03-07)

Based on both binding and functional data, this study introduces SR 144528 as the first, highly potent, selective and orally active antagonist for the CB2 receptor. This compound which displays subnanomolar affinity (Ki = 0.6 nM) for both the rat

Inhibitory effect of cannabinoid agonists on gastric emptying in the rat.

A A Izzo et al.

Naunyn-Schmiedeberg's archives of pharmacology, 360(2), 221-223 (1999-09-24)

We have studied the effect of WIN 55,212-2 (a psychoactive cannabinoid agonist), cannabinol (a nonpsychoactive cannabinoid agonist), SR141716A, a cannabinoid CB1 antagonist, and SR144528, a cannabinoid CB2 antagonist, on gastric emptying in the rat. WIN 55,212-2 (0.1-5 mg/kg, i.p.) and

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Global Trade Item Number

SKU	GTIN
SML1899-5MG	04061832561141
SML1899-25MG	04061832561134