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Merck
CN

U105

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
NACRES:
NA.77
PubChem Substance ID:
24278071
UNSPSC Code:
12352200
MDL number:
MFCD00153876

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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

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 key

FHEZDPDAYTVKKG-JLBKCEDKSA-N

form

solid

color

white

solubility

H2O: 14 mg/mL, methanol: insoluble

storage temp.

2-8°C

Quality Level

200

Gene Information

human ... OPRK1(4986)

Related Categories

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
028H4691V

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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
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
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
J Kamei et al.
European journal of pharmacology, 187(2), 281-286 (1990-10-09)
The effects of highly selective agonists of kappa-opioid receptors, namely U-50,488H and U-62,066E, on the capsaicin-induced cough reflex in rats were studied. Intracisternal (i.cist.) injection of U-50,488H and of U-62,066E significantly decreased the number of coughs in a dose-dependent manner.
Jolan M Terner et al.
Behavioural pharmacology, 16(8), 665-670 (2005-11-16)
Although studies suggest that 2-(3,4-dichlorophenyl-N-methyl-N-[(1S)-1-(3-isothiocyanatophenyl)-2-(1-pyrrolidinyl) ethyl] acetamide (DIPPA) has transient kappa-opioid-mediated agonist effects followed by long-lasting kappa-antagonist effects, its behavioral and pharmacological actions have not been systematically examined and there is evidence suggesting that some of its effects are species
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