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| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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≥98% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Store at 2-8°C,Argon charged,Desiccated Ships Wet ice Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Asimadoline (EMD-61753) hydrochloride is an orally active, selective and peripherally active κ-opioid agonist with IC 50 s of 5.6 nM (guinea pig) and 1.2 nM (human recombinant). Asimadoline hydrochloride has low permeability across the blood brain barrier and has peripheral anti-inflammatory actions. Asimadoline hydrochloride ameliorates allodynia in diabetic rats and has the potential for irritable bowel syndrome (IBS)
In Vitro
Asimadoline (EMD-61753) hydrochloride has high selectively in κ: μ: δ opioid binding ratios of 1:501:498 in human recombinant receptors. The IC 50 for Asimadoline hydrochloride binding to μ-opioid receptors is 3 µM and to δ-opioid receptors is 0.7 µM. The IC 50 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 µM. Asimadoline hydrochloride has affinity to sodium and L type Ca 2+ ion channels at IC 50 concentrations 150 to 800 fold the IC 50 for the κ receptors. At high concentrations, Asimadoline hydrochloride demonstrates spasmolytic action against 400 µM barium chloride in the rat duodenum (IC 50 =4.2 µM), suggesting that Asimadoline hydrochloride may block the direct stimulant effects of barium on smooth muscle through mechanisms that are not identified. MCE has not independently confirmed the accuracy of these methods. They are for reference only.
In Vivo
Asimadoline (EMD-61753 hydrochloride; 1, 5, 15 mg/kg; s.c.) acutely ameliorates both formalin-evoked hyperalgesia and tactile allodynia in diabetic rats. The absorption rate following oral administration is 80% in rats and >90% in dogs and monkeys. The metabolism of Asimadoline hydrochloride is rapid and appears similar in animals and man. Asimadoline hydrochloride has peripheral anti-inflammatory actions that are partly mediated through increase in joint fluid substance P levels . Treatment with Asimadoline hydrochloride (5 mg/kg/day; i.p.) produces marked (and sustained) attenuation of the disease with all three time regimes. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Animal Model: Adult female Sprague-Dawley ratsDosage: 1, 5, 15 mg/kg Administration: SC; single dose Result: Acutely ameliorated both formalin-evoked hyperalgesia and tactile allodynia in diabetic rats.
Form:Solid
IC50& Target:IC50: 5.6 nM (guinea pig κ opioid), 1.2 nM (human recombinant κ opioid)
| Sonrisas canónicas | CN(C(CN1CCC(C1)O)C2=CC=CC=C2)C(=O)C(C3=CC=CC=C3)C4=CC=CC=C4.Cl |
|---|---|
| IUPAC Name | N-[(1S)-2-[(3S)-3-hydroxypyrrolidin-1-yl]-1-phenylethyl]-N-methyl-2,2-diphenylacetamide;hydrochloride |
| InChIKey | GMJSLABTEURMBF-CLSOAGJSSA-N |
| INCHI | 1S/C27H30N2O2.ClH/c1-28(25(21-11-5-2-6-12-21)20-29-18-17-24(30)19-29)27(31)26(22-13-7-3-8-14-22)23-15-9-4-10-16-23;/h2-16,24-26,30H,17-20H2,1H3;1H/t24-,25+;/m0./s1 |
| Isómeros SMILES | CN([C@H](CN1CC[C@@H](C1)O)C2=CC=CC=C2)C(=O)C(C3=CC=CC=C3)C4=CC=CC=C4.Cl |
| CAS alternativo | 153205-46-0 (free base) |
| PubChem CID | 9846614 |
| Peso molecular | 451.01 |
Comprehensive hazard, handling, storage, and regulatory compliance document.
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View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Benzenoids |
| Clase | Benzene and substituted derivatives |
| Subclass | Diphenylmethanes |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Diphenylmethanes |
| Alternative Parents | Phenylacetamides Aralkylamines N-alkylpyrrolidines Tertiary carboxylic acid amides Trialkylamines Secondary alcohols Amino acids and derivatives 1,2-aminoalcohols Azacyclic compounds Organic oxides Hydrochlorides Hydrocarbon derivatives Carbonyl compounds |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Diphenylmethane - Phenylacetamide - Aralkylamine - N-alkylpyrrolidine - Pyrrolidine - Tertiary carboxylic acid amide - 1,2-aminoalcohol - Amino acid or derivatives - Carboxamide group - Secondary alcohol - Tertiary amine - Tertiary aliphatic amine - Carboxylic acid derivative - Azacycle - Organoheterocyclic compound - Alcohol - Organic oxygen compound - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Amine - Organic oxide - Carbonyl group - Hydrocarbon derivative - Hydrochloride - Aromatic heteromonocyclic compound |
| Descripción | This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. |
| External Descriptors | Not available |
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| Solubilidad | DMSO : 240 mg/mL (532.15 mM; Need ultrasonic) |
|---|---|
| Sensibilidad | Moisture sensitive |
| Peso molecular | 451.000 g/mol |
| XLogP3 | |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 7 |
| Exact Mass | 450.207 Da |
| Monoisotopic Mass | 450.207 Da |
| Topological Polar Surface Area | 43.800 Ų |
| Heavy Atom Count | 32 |
| Formal Charge | 0 |
| Complexity | 531.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 2 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 2 |