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U105

Sigma-Aldrich

U-62066

solid

Synonym(s):

(±)-(5α,7α,8β)-3,4-Dichloro-N-methyl-N-[7-(1-pyrrolidinyl)-1-oxaspiro[4.5]dec-8-yl]benzeneacetamide mesylate salt, Spiradoline mesylate salt

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About This Item

Linear Formula:
C22H30Cl2N2O2 · CH3SO3H
CAS Number:
87151-85-7
Molecular Weight:
521.50
MDL number:
MFCD00153876
UNSPSC Code:
12352200
PubChem Substance ID:
24278071
NACRES:
NA.77

form

solid

color

white

solubility

H2O: 14 mg/mL
methanol: insoluble

storage temp.

2-8°C

SMILES string

CS(O)(=O)=O.CN([C@H]1CC[C@@]2(CCCO2)C[C@@H]1N3CCCC3)C(=O)Cc4ccc(Cl)c(Cl)c4

InChI

1S/C22H30Cl2N2O2.CH4O3S/c1-25(21(27)14-16-5-6-17(23)18(24)13-16)19-7-9-22(8-4-12-28-22)15-20(19)26-10-2-3-11-26;1-5(2,3)4/h5-6,13,19-20H,2-4,7-12,14-15H2,1H3;1H3,(H,2,3,4)/t19-,20-,22-;/m0./s1

InChI key

FHEZDPDAYTVKKG-JLBKCEDKSA-N

Gene Information

human ... OPRK1(4986)

Biochem/physiol Actions

U-62066, also known as spiradoline, is a highly selective κ opioid receptor agonist. It exhibits analgesic and diuretic effects. Antitussive property of U-62066 is observed in rats.

Preparation Note

U-62066 is soluble in water at 14 mg/ml, but is insoluble in methanol.

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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M A Smith et al.
Behavioural pharmacology, 14(8), 641-647 (2003-12-11)
The purpose of the present study was to examine sensitivity to the antinociceptive effects of kappa opioids during chronic treatment with the nonselective opioid antagonist naltrexone. In a warm-water tail-withdrawal procedure, rats were restrained and the latencies to remove their
Shannon L Briggs et al.
Pharmacology, biochemistry, and behavior, 92(2), 343-350 (2009-04-09)
Interactions of opioid agonists, fentanyl and oxymorphone (micro-selective) and spiradoline and enadoline(kappa-selective), were examined for additive, sub-additive, or supra-additive antinociception in the colorectal distension (CRD) assay. Single-dose values (mg/kg, 0.006-0.016 for fentanyl, 0.25-1.26 forspiradoline, etc.) were summed to formulate theoretical
S G Holtzman
Pharmacology, biochemistry, and behavior, 66(3), 517-522 (2000-07-19)
The results of a previous study in rats indicated that spiradoline has pharmacologically selective discriminative effects that are mediated by kappa-opioid receptors. However, the training dose, 3.0 mg/kg, increased response latencies, suggesting that it was relatively high. The current study
Glenn R Valdez et al.
The Journal of pharmacology and experimental therapeutics, 323(2), 525-533 (2007-08-19)
Kappa opioid agonists were at one time proposed as candidate pharmacotherapies for cocaine addiction, mainly because of their ability to decrease dopamine neurotransmission and attenuate the behavioral effects of cocaine in laboratory animals. Recent studies, however, suggest that kappa agonists
M K Pugsley et al.
Journal of cardiovascular pharmacology, 32(6), 863-874 (1998-12-30)
Spiradoline (U-62,066E), a selective kappa (kappa) receptor agonist, was examined for actions on the cardiovascular system and on myocardial ionic currents in rats. We initially characterized cardiac, hemodynamic, and antiarrhythmic actions of spiradoline in isolated perfused rat hearts and pentobarbital-anesthetized
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