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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

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

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K Rasakham et al.
Neuroscience, 223, 447-456 (2012-08-07)
Recently there has been a widespread interest in the development of kappa opioid receptor (KOPR) ligands for treatment of pain, depression and anxiety, and prevention of stress-induced drug relapse. However, most of these preclinical studies have been conducted using male
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Neuroscience letters, 524(2), 111-115 (2012-07-24)
Activation of peripheral κ opioid receptors (KOR) effectively relieves pain and hyperalgesia in preclinical and clinical models of pain. Although centrally located KOR activation results in sexually dimorphic effects, it is unclear whether peripheral KOR also produces sex dependent effects
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.
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
Bassil Hassan et al.
Regional anesthesia and pain medicine, 38(1), 21-27 (2012-12-12)
κ-Opioid receptor (κ-OR) activation is known to play a role in analgesia and central sedation. The purpose of the present study was to examine the effect of the κ-OR agonist, U-50488 (an arylacetamide), on Ca channel currents and the signaling
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