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G133

Sigma-Aldrich

GR 89696 fumarate salt

solid

Synonym(s):

4-[(3,4-Dichlorophenyl)acetyl]-3-(1-pyrrolidinylmethyl)-1-piperazinecarboxylic acid methyl ester fumarate salt

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About This Item

Empirical Formula (Hill Notation):
C19H25Cl2N3O3 · C4H4O4
CAS Number:
126766-32-3
Molecular Weight:
530.40
MDL number:
MFCD00274044
UNSPSC Code:
12352200
PubChem Substance ID:
24278038
NACRES:
NA.77

form

solid

color

off-white

solubility

ethanol: 4.0 mg/mL
DMSO: >50 mg/mL
H2O: 8.5 mg/mL

SMILES string

OC(=O)\C=C\C(O)=O.COC(=O)N1CCN(C(CN2CCCC2)C1)C(=O)Cc3ccc(Cl)c(Cl)c3

InChI

1S/C19H25Cl2N3O3.C4H4O4/c1-27-19(26)23-8-9-24(15(13-23)12-22-6-2-3-7-22)18(25)11-14-4-5-16(20)17(21)10-14;5-3(6)1-2-4(7)8/h4-5,10,15H,2-3,6-9,11-13H2,1H3;1-2H,(H,5,6)(H,7,8)/b;2-1+

InChI key

ABTNETSDXZBJTE-WLHGVMLRSA-N

Gene Information

human ... OPRK1(4986)

Application

GR 89696 fumarate salt has been used as a κ κ2 opioid receptor (KOR) agonist to study its anti-scratching and antipruritic effects on monkeys.

Biochem/physiol Actions

GR 89696 fumarate is a selective κ2 opioid receptor agonist.

Legal Information

Sold for research purposes under agreement from Glaxo­Smith­Kline

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)

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Mei-Chuan Ko et al.
The Journal of pharmacology and experimental therapeutics, 328(1), 193-200 (2008-10-10)
Itch/pruritus is the most common side effect associated with spinal administration of morphine given to humans for analgesia. The aim of this study was to investigate the effectiveness of kappa-opioid receptor (KOR) agonists with diverse chemical structures as antipruritics and
B Fry et al.
Neuropeptides, 35(3-4), 154-161 (2002-03-09)
Isometric muscle contractions cause an increase in mean arterial pressure and heart rate. Previously, we showed that substance P (SP) is released from sites in the feline medial nucleus tractus solitarius (mNTS) in response to isometric muscle contractions, and that
A Butler et al.
British journal of pharmacology, 109(1), 126-130 (1993-05-01)
1. Effects of the alpha 2-adrenoceptor agonists, UK14304 and clonidine, the 5-HT1 receptor agonist, sumatriptan and the kappa-opioid receptor agonist, GR103545, on sensory neurotransmission in histamine-contracted guinea-pig isolated pulmonary artery (GPPA) have been studied. 2. Electrical field stimulation (EFS) induced
R M Caudle et al.
The Journal of pharmacology and experimental therapeutics, 283(3), 1342-1349 (1998-02-12)
Receptor binding studies and electrophysiological studies demonstrated the existence of at least two kappa opioid receptors, which have been designated kappa-1 and kappa-2. Several agonists and antagonists are selective for the kappa-1 receptor whereas no known ligands are selective for
A Naylor et al.
Journal of medicinal chemistry, 36(15), 2075-2083 (1993-07-23)
The synthesis of 4-substituted 1-(arylacetyl)-2-[(alkylamino)methyl]piperazines (10-22, 26, 27, and 30-33) and their activities as kappa-opioid receptor agonists are described. This includes a range of 4-acyl and 4-carboalkoxy derivatives with the latter series showing the greatest kappa-agonist activity. In particular, methyl
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