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U111

Sigma-Aldrich

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

solid, ≥98% (HPLC)

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Synonym(s):
trans-(1S,2S)-3,4-Dichloro-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]benzeneacetamide hydrochloride hydrate
Empirical Formula (Hill Notation):
C19H26Cl2N2O · HCl · xH2O
CAS Number:
Molecular Weight:
405.79 (anhydrous basis)
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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)

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This Item
D8040B2417N0287
Benzamil hydrochloride hydrate ≥98% (HPLC)

B2417

Benzamil hydrochloride hydrate

NNC 55-0396 hydrate ≥98% (HPLC)

N0287

NNC 55-0396 hydrate

assay

≥98% (HPLC)

assay

-

assay

≥98% (HPLC)

assay

≥98% (HPLC)

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage condition

desiccated

storage condition

-

storage condition

desiccated

storage condition

desiccated

solubility

H2O: 13 mg/mL

solubility

H2O: 50 mg/mL

solubility

methanol: 10 mg/mL, DMSO: >20 mg/mL

solubility

H2O: >10 mg/mL

color

white

color

-

color

yellow

color

white

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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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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