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Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
YS-201 is a dihydropyridine-type calcium channel antagonist. YS-201 has the potential for angina pectoris and hypertension treatment.
In Vivo
YS-201 (Diperdipine) markedly reduces systemic vascular resistance and improves stroke index and left ventricular ejection fraction. Mean pulmonary artery and wedge pressures are slightly increased as a possible consequence of enhanced venous return, whereas right atrial and left ventricular end-diastolic pressures are not significantly changed. Nevertheless, an increase in preload is clearly indicated by an augmented left ventricular end-diastolic volume index after administration of diperdipine . After intravenous and oral doses, absolute bioavailability is calculated to be 18.7%. Biliaryexcretion accounts for about 0.1% of the total clearance of diperdipine and does not contribute to the overall elimination of the drug. After intraportal administration, the bioavailable fraction of diperdipine is increasing up to 44.3% suggesting a prehepatic site of loss of the drug. The single application of diperdipine to mice and rats by gavage causes intolerance reactions starting at the lowest tested dose level of 200 mg/kg b.w. p.o. (mice) and at 250 mg/kg b.w. p.o. (rats). In the rat, toxic effects occur from 15 mg diperdipine/kg b.w./day p.o. onwards. MCE has not independently confirmed the accuracy of these methods. They are for reference only.
Form:Solid
| Canonical Smiles | CCOC(=O)C1=C(NC(=C(C1C2=CC(=CC=C2)[N+](=O)[O-])C(=O)OCCN3CCCCC3)C)C |
|---|---|
| IUPAC Name | 3-O-ethyl 5-O-(2-piperidin-1-ylethyl) 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate |
| InChIKey | LBSRZVRITCRLIU-UHFFFAOYSA-N |
| INCHI | 1S/C24H31N3O6/c1-4-32-23(28)20-16(2)25-17(3)21(22(20)18-9-8-10-19(15-18)27(30)31)24(29)33-14-13-26-11-6-5-7-12-26/h8-10,15,22,25H,4-7,11-14H2,1-3H3 |
| Isomeric SMILES | CCOC(=O)C1=C(NC(=C(C1C2=CC(=CC=C2)[N+](=O)[O-])C(=O)OCCN3CCCCC3)C)C |
| Alternate CAS | 108852-42-2 |
| PubChem CID | 130588 |
| MeSH Entry Terms | diperdipine;EPDDNP;ethyl-2-(1-piperidino)ethyl-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridine dicarboxylate |
| Molecular Weight | 457.52 |
Comprehensive hazard, handling, storage, and regulatory compliance document.
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View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organoheterocyclic compounds |
| Class | Pyridines and derivatives |
| Subclass | Hydropyridines |
| Intermediate Tree Nodes | Dihydropyridines |
| Direct Parent | Dihydropyridinecarboxylic acids and derivatives |
| Alternative Parents | Nitrobenzenes Nitroaromatic compounds Piperidines Dicarboxylic acids and derivatives Vinylogous amides Enoate esters Trialkylamines Amino acids and derivatives Propargyl-type 1,3-dipolar organic compounds Organic oxoazanium compounds Enamines Dialkylamines Azacyclic compounds Organopnictogen compounds Organic zwitterions Organic oxides Hydrocarbon derivatives Carbonyl compounds |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Nitrobenzene - Dihydropyridinecarboxylic acid derivative - Nitroaromatic compound - Benzenoid - Piperidine - Dicarboxylic acid or derivatives - Monocyclic benzene moiety - Vinylogous amide - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Organic nitro compound - Tertiary aliphatic amine - Tertiary amine - C-nitro compound - Carboxylic acid ester - Amino acid or derivatives - Azacycle - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Allyl-type 1,3-dipolar organic compound - Secondary amine - Organic oxoazanium - Enamine - Secondary aliphatic amine - Carboxylic acid derivative - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organic zwitterion - Organooxygen compound - Organonitrogen compound - Carbonyl group - Amine - Aromatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as dihydropyridinecarboxylic acids and derivatives. These are compounds containing a dihydropyridine moiety bearing a carboxylic acid group. |
| External Descriptors | Not available |
| Molecular Weight | 457.500 g/mol |
|---|---|
| XLogP3 | 3.800 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 9 |
| Exact Mass | 457.221 Da |
| Monoisotopic Mass | 457.221 Da |
| Topological Polar Surface Area | 114.000 Ų |
| Heavy Atom Count | 33 |
| Formal Charge | 0 |
| Complexity | 810.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 1 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |
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