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I122

Sigma-Aldrich

ICI 204,448 hydrochloride

solid

Synonym(s):

(±)-1-[2,3-(Dihydro-7-methyl-1H-inden-4-yl)oxy]-3-[(1-methylethyl)amino]-2-butanol hydrochloride, R,S-[3-[1-[[(3,4-Dichlorophenyl)acetyl]methylamino]-2-(1-pyrrolidinyl)ethyl] phenoxy]-acetic acid hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C23H26Cl2N2O4 · HCl
CAS Number:
121264-04-8
Molecular Weight:
501.83
MDL number:
MFCD00153814
UNSPSC Code:
12352200
PubChem Substance ID:
24278040
NACRES:
NA.77

form

solid

color

white

solubility

45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 12 mg/mL
dilute sodium carbonate: 4 mg/mL
H2O: 4.5 mg/mL

SMILES string

Cl[H].CN(C(CN1CCCC1)c2cccc(OCC(O)=O)c2)C(=O)Cc3ccc(Cl)c(Cl)c3

InChI

1S/C23H26Cl2N2O4.ClH/c1-26(22(28)12-16-7-8-19(24)20(25)11-16)21(14-27-9-2-3-10-27)17-5-4-6-18(13-17)31-15-23(29)30;/h4-8,11,13,21H,2-3,9-10,12,14-15H2,1H3,(H,29,30);1H

InChI key

FNDGLVOYAQNQPE-UHFFFAOYSA-N

Gene Information

human ... OPRK1(4986)

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Biochem/physiol Actions

κ opioid receptor agonist that does not cross the blood-brain barrier.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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E R Butelman et al.
Psychopharmacology, 147(1), 73-80 (1999-12-11)
The dynorphins are endogenous opioid peptides with relative binding selectivity for kappa-receptors. It is unclear whether the dynorphins share the pharmacological profile observed with synthetic kappa-agonists in primates. The main objective of this study was to compare the effects of
A Barber et al.
British journal of pharmacology, 113(4), 1317-1327 (1994-12-01)
1. The pharmacological properties of the novel diarylacetamide kappa-opioid receptor agonist, EMD 61753, have been compared with those of ICI 197067 (a centrally-acting kappa agonist) and ICI 204448 (a peripherally-selective kappa agonist). 2. EMD 61753 binds with high affinity (IC50
H Keïta et al.
European journal of pharmacology, 277(2-3), 275-280 (1995-04-24)
The antinociceptive effect of intraplantar (i.pl.) ICI 204448 ((R,S)-N-[2-(N-methyl-3,4-dichloro-phenylacetamido)-2-(3-carbox yph enyl)- ethyl]pyrrolidine hydrochloride)) (20, 30, 40 and 50 micrograms), a kappa-opioid receptor agonist which has limited access to the central nervous system, was studied in a well-established rat model of
R A Hirst et al.
Neuroscience letters, 232(2), 119-122 (1997-08-29)
This study describes the coupling of the recombinant rat kappa-opioid receptor expressed in Chinese hamster ovary (CHO) cells to adenylyl cyclase and the effects of receptor density. The binding of [3H]diprenorphine ([3H]DPN) was dose dependent and saturable in membranes prepared
Scott M Rawls et al.
Pharmacology, 74(2), 79-83 (2005-02-03)
ICI 204448, a selective kappa-opioid agonist with limited CNS access, can be used to discriminate central and peripheral opioid actions on physiological systems such as pain and thermoregulation. Therefore, we investigated the effect of ICI 204448 (2.5, 5, and 10
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