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U111

Sigma-Aldrich

(−)-trans-(1S,2S)-U-50488 hydrochloride hydrate

solid, ≥98% (HPLC)

Synonym(s):

trans-(1S,2S)-3,4-Dichloro-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]benzeneacetamide hydrochloride hydrate

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About This Item

Empirical Formula (Hill Notation):
C19H26Cl2N2O · HCl · xH2O
CAS Number:
114528-79-9
Molecular Weight:
405.79 (anhydrous basis)
MDL number:
MFCD11044455
UNSPSC Code:
12352200
PubChem Substance ID:
24278019
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

solid

optical activity

[α]22/D -39.0 to -32.0°, c = 0.5 in methanol(lit.)

storage condition

desiccated

color

white

solubility

H2O: 13 mg/mL

storage temp.

2-8°C

SMILES string

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

InChI

1S/C19H26Cl2N2O.ClH.H2O/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;;/h8-9,12,17-18H,2-7,10-11,13H2,1H3;1H;1H2/t17-,18-;;/m0../s1

InChI key

UWPRPWMHQDPOFR-MPGISEFESA-N

Gene Information

human ... OPRK1(4986)

Application

(−)-trans-(1S,2S)-U-50488 hydrochloride hydrate (U-50488) has been used as a κ-opioid receptor (KOR) agonist has been used to study its effect on the increase of tidal volumes in adult red-eared slider turtles (Trachemys scripta).

Biochem/physiol Actions

Potent κ opioid receptor agonist; more potent enantiomer of (±)-trans-U-50488.

Preparation Note

(−)-trans-(1S,2S)-U-50488 hydrochloride hydrate is soluble in water at 13 mg/ml.

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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D D Taub et al.
Proceedings of the National Academy of Sciences of the United States of America, 88(2), 360-364 (1991-01-15)
Opioids and opioid peptides have been shown by numerous laboratories to modulate various parameters of the immune response, but little attention has been given to the type of opioid receptor that might be involved. This study focuses on the in
Stereospecific inhibition of gastro-intestinal transit by κ-opioid agonists in mice.
Ramabadran, et al.
European Journal of Pharmacology, 155, 329-329 (1991)
Stephen M Johnson et al.
American journal of physiology. Regulatory, integrative and comparative physiology, 295(5), R1599-R1612 (2008-09-12)
For ectothermic vertebrates, such as reptiles, the effects of opioid receptor subtype activation on breathing are poorly understood. On the basis of previous studies on mammals and lampreys, we hypothesized that mu- and delta-opioid receptor (MOR and DOR, respectively) activation

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