CAS 153205-46-0|Asimadoline

Introduction：Basic information about CAS 153205-46-0|Asimadoline, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Asimadoline BiologicalActivity
3. Chemical & Physical Properties
4. Synonyms

Common Name	Asimadoline
CAS Number	153205-46-0	Molecular Weight	414.539
Density	1.2±0.1 g/cm3	Boiling Point	605.8±55.0 °C at 760 mmHg
Molecular Formula	C₂₇H₃₀N₂O₂	Melting Point	/
MSDS	/	Flash Point	320.2±31.5 °C

Names

Name	N-[(1S)-2-[(3S)-3-hydroxypyrrolidin-1-yl]-1-phenylethyl]-N-methyl-2,2-diphenylacetamide
Synonym	More Synonyms

Asimadoline BiologicalActivity

Description	Asimadoline is a potent κ opioid receptor agonist with IC50s of 5.6 and 1.2 nM for guinea pig and human recombinant κ opioid receptor, respectively.
Related Catalog	Signaling Pathways >>GPCR/G Protein >>Opioid ReceptorSignaling Pathways >>Neuronal Signaling >>Opioid ReceptorResearch Areas >>Inflammation/Immunology
Target	IC50: 5.6 nM (guinea pig κ opioid), 1.2 nM (human recombinant κ opioid)[1]
In Vitro	The IC50 for Asimadoline binding to μ-opioid receptors is 3 µM and to δ-opioid receptors is 0.7 µM. The IC50 values for D1, D2, kainate, σ, PCP/NMDA, H1, α1, α2, M1/M2, glycine, 5HT1A, 5HT1C, 5HT1D, 5HT2, 5HT3, AMPA and kainate/AMPA receptors are all >10 IC50, suggesting no relevant antihistaminergic, antiserotonergic or anticholinergic effects. At high concentrations, Asimadoline demonstrates spasmolytic action against 400 µM barium chloride in the rat duodenum (IC50=4.2 µM), suggesting that Asimadoline may block the direct stimulant effects of barium on smooth muscle through mechanisms that are not identified[1].
In Vivo	The absorption rate following oral administration is 80% in rats and >90% in dogs and monkeys. The metabolism of Asimadoline is rapid and appears similar in animals and man. Asimadoline has peripheral anti-inflammatory actions that are partly mediated through increase in joint fluid substance P levels[1]. Treatment with Asimadoline (5 mg/kg/day i.p.) produces marked (and sustained) attenuation of the disease with all three time regimes[2].
Animal Admin	Rats: Asimadoline (5 mg/kg/day, n=10 per group) or vehicle (2 mL/kg/day, n=10) is administered to DA rats by i.p. injection twice daily (i) during the primary inflammatory phase (days 1–3); (ii) once the disease is established (days 13–21); or (iii) throughout the entire time course (days 1-21). Non-arthritic control animals receive Asimadoline (5 mg/kg/day, n=5) or vehicle (2 mL/kg/day, n=5) by i.p. injection twice daily. In all cases, disease parameters are assessed. In this experiment, the SP content of joint tissue is assessed only after the rats are killed (day 21)[2].
References	[1]. Camilleri M, et al. Asimadoline, a κ-Opioid Agonist, and Visceral Sensation. Neurogastroenterol Motil. 2008 Sep; 20(9): 971–979. [2]. Binder W, et al. Involvement of substance P in the anti-inflammatory effects of the peripherally selective kappa-opioid asimadoline and the NK1 antagonist GR205171. Eur J Neurosci. 1999 Jun;11(6):2065-72.

Chemical & Physical Properties

Density	1.2±0.1 g/cm3
Boiling Point	605.8±55.0 °C at 760 mmHg
Molecular Formula	C₂₇H₃₀N₂O₂
Molecular Weight	414.539
Flash Point	320.2±31.5 °C
Exact Mass	414.230713
PSA	43.78000
LogP	3.71
Vapour Pressure	0.0±1.8 mmHg at 25°C
Index of Refraction	1.617
InChIKey	JHLHNYVMZCADTC-LOSJGSFVSA-N
SMILES	CN(C(=O)C(c1ccccc1)c1ccccc1)C(CN1CCC(O)C1)c1ccccc1
Storage condition	-20℃

Synonyms

N-((1S)-2-((3S)-3-hydroxy-1-pyrrolidinyl)-1-phenylethyl)-N-methyl-2,2-diphenylacetamide

UNII-D0VK52NV5M

Asimadoline

Benzeneacetamide, N-((1S)-2-((3S)-3-hydroxy-1-pyrrolidinyl)-1-phenylethyl)-N-methyl-α-phenyl-

Benzeneacetamide, N-[(1S)-2-[(3S)-3-hydroxy-1-pyrrolidinyl]-1-phenylethyl]-N-methyl-α-phenyl-

N-((aS)-a-(((3S)-3-Hydroxy-1-pyrrolidinyl)methyl)benzyl)-N-methyl-2,2-diphenylacetamide

N-{(1S)-2-[(3S)-3-Hydroxy-1-pyrrolidinyl]-1-phenylethyl}-N-methyl-2,2-diphenylacetamide

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