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Merck
CN

U106

Sigma-Aldrich

(−)-cis-(1S,2R)-U-50488 tartrate

solid

Synonym(s):

(−)-(1S,2R)-cis-3,4-Dichloro-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]benzeneacetamide tartrate

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About This Item

Empirical Formula (Hill Notation):
C19H26Cl2N2O · C4H6O6
CAS Number:
121843-48-9
Molecular Weight:
519.42
MDL number:
MFCD00153875
UNSPSC Code:
12352200
PubChem Substance ID:
24278550

Key Documents

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form

solid

color

white

solubility

ethanol: soluble

storage temp.

2-8°C

SMILES string

OC(C(O)C(O)=O)C(O)=O.CN([C@H]1CCCC[C@H]1N2CCCC2)C(=O)Cc3ccc(Cl)c(Cl)c3

InChI

1S/C19H26Cl2N2O.C4H6O6/c1-22(19(24)13-14-8-9-15(20)16(21)12-14)17-6-2-3-7-18(17)23-10-4-5-11-23;5-1(3(7)8)2(6)4(9)10/h8-9,12,17-18H,2-7,10-11,13H2,1H3;1-2,5-6H,(H,7,8)(H,9,10)/t17-,18+;/m0./s1

InChI key

DMBKHRMAGYYBJM-CJRXIRLBSA-N

Gene Information

human ... OPRS1(10280)

Biochem/physiol Actions

Potent σ receptor ligand.

Preparation Note

(-)-cis-(1S,2R)-U-50488 tartrate is soluble in ethanol.

Storage Class Code

13 - Non 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

Regulatory Information

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Amber D Shaffer et al.
Neuroscience letters, 534, 150-154 (2012-12-04)
Previous research has suggested that early-in-life (EIL) exposure to bladder inflammation impairs the function of endogenous opioid inhibitory system(s) and may contribute to the development of chronic bladder pain. This study examined how acute adult and/or prior EIL exposure to
A A Spasov et al.
Eksperimental'naia i klinicheskaia farmakologiia, 74(8), 45-47 (2012-01-12)
A new model is proposed for in vitro testing the efficiency of new chemical substances with kappa-opioid receptor agonist ligand properties.
Jeffrey S Smith et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 32(4), 1488-1495 (2012-01-27)
Many smokers describe the anxiolytic and stress-reducing effects of nicotine, the primary addictive component of tobacco, as a principal motivation for continued drug use. Recent evidence suggests that activation of the stress circuits, including the dynorphin/κ-opioid receptor system, modulates the
JiaJi Lin et al.
Cytokine, 61(3), 842-848 (2013-02-14)
It is well documented that the Toll-like receptor 4 (TLR4)/NF-κB signaling mediates early inflammation during myocardial ischemia and reperfusion. Our previous study has demonstrated that κ-opioid receptor stimulation with U50,488H produces cardioprotective and anti-inflammatory effects. The aim of the present
B R de Costa et al.
Journal of medicinal chemistry, 32(8), 1996-2002 (1989-08-01)
The synthesis and in vitro sigma receptor activity of the two diastereomers of U50,488 [(+/-)-2], namely, (1R,2S)-(+)- cis-3,4-dichloro-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]benzeneacet ami de [(+)-1] and (1S,2R)-(-)-cis-3,4-dichloro- N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]benzeneacetamide [(-)-1], are described. (+)-1 and (-)-1 were synthesized from (+/-)-trans-N-methyl-2-aminocyclohexanol [(+/-)-3]. Pyridinium chlorochromate (PCC) oxidation of
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