Asimadoline (EMD-61753)

Cas No.:	153205-46-0
Chemical Name:	Benzeneacetamide,N-[(1S)-2-[(3S)-3-hydroxy-1-pyrrolidinyl]-1-phenylethyl]-N-methyl-a-phenyl-
Synonyms:	Benzeneacetamide,N-[(1S)-2-[(3S)-3-hydroxy-1-pyrrolidinyl]-1-phenylethyl]-N-methyl-a-phenyl-;C27H30N2O2;N-[(1S)-2-[(3S)-3-hydroxypyrrolidin-1-yl]-1-phenylethyl]-N-methyl-2,2-diphenylacetamide;Asimadoline;UNII-D0VK52NV5M;N-[(1S)-2-[(3S)-3-Hydroxy-1-pyrrolidinyl]-1-phenylethyl]-N-methyl-alpha-phenylbenzeneacetamide;EMD 61753
SMILES:	O=C(N([C@@H](C1=CC=CC=C1)CN2C[C@@H](O)CC2)C)C(C3=CC=CC=C3)C4=CC=CC=C4
Formula:	C27H30N2O2
M.Wt:	414.5393
Purity:	>98%
Sotrage:	2 years -20°C Powder, 2 weeks 4°C in DMSO, 6 months -80°C in DMSO

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.
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].
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].