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(-)-3-(3,4-Dimethoxyphenyl)-6-[(5,6-dimethoxyphenethyl)methylamino]hexan-3-carbonitril
l-Verapamil · S-Verapamil HCI · Einecs 253-133-3 · (-)-3-(3,4-dimethoxyphenyl)-6-[(5,6-dimethoxyphenethyl)methylamino]hexane-3-carbonitrile · l-a-Isopropyl-a-[(N-methyl-N-homoveratryl)-g-aminopropyl]-3,4-dimethoxyphenylacetonitrile · (S)-5-[(3,4-Dimethoxyphenethyl)methylamino]-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile · [S,(-)]-2-(3,4-Dimethoxyphenyl)-2-isopropyl-5-(N-methyl-3,4-dimethoxyphenethylamino)valeronitrile · (-)-(S)-5-[N-[2-(3,4-Dimethoxyphenyl)ethyl]-N-methylamino]-2-(3,4-dimethoxyphenyl)-2-isopropylpentanenitrile
![Molekülstruktur von (-)-3-(3,4-Dimethoxyphenyl)-6-[(5,6-dimethoxyphenethyl)methylamino]hexan-3-carbonitril](/img/chemical/2520.png)
Identifikatoren & physikalische Daten
| CAS No. | 36622-29-4 |
|---|---|
| Summenformel | C27H38N2O4 |
| Durchschnittliche Molmasse | 454,6 g/mol |
| Monoisotopische Masse | 454,2831577 g/mol |
| SMILES | COc1ccc(CCN(C)CCCC(C#N)(c2ccc(OC)c(OC)c2)C(C)C)cc1OC |
| InChIKey | SGTNSNPWRIOYBX-UHFFFAOYSA-N |
| PubChem CID | 2520 |
| ChEMBL | CHEMBL6966 |
| ChEBI | CHEBI:77733 |
| EC No. | 200-145-1 |
| DTXSID | DTXSID9041152 |
| Lokaler Name | (-)-3-(3,4-Dimethoxyphenyl)-6-[(5,6-dimethoxyphenethyl)methylamino]hexan-3-carbonitril |
Chemische & physikalische Eigenschaften
| XLogP | 3,8 |
|---|---|
| Polarare Oberfläche (TPSA) | 64 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 6 |
| Frei drehbare Bindungen | 13 |
| Schwere Atome | 33 |
| Formalladung | 0 |
| Komplexität | 606 |
| Stoffklassen | Pharmaceutical |
| Arzneimittel | Pharmaceuticals -> Used in Switzerland |
| LogP (Verteilungskoeffizient) | log Kow = 3.79 at pH 9.0log Kow = 2.15 at pH 7.0 |
| Color/Form | Viscous, pale yellow oil |
| Löslichkeit | Solubility (mg/mL): water 83, ethanol (200 proof) 26, propylene glycol 93, ethanol (190 proof) >100, methanol >100, 2-propanol 4.6, ethyl acetate 1.0, DMF >100, methylene chloride >100, hexane 0.001Freely soluble in chloroform, practically insoluble in ether /Verapamil hydrochloride/Practically insoluble in waterSparingly soluble in hexanesoluble in benzene, etherfreely soluble in the lower alcohols, acetone, ethyl acetate, chloroform4.47 mg/L |
| Human Drugs | Breast FeedingLactationMilk, HumanAntihypertensive AgentsCalcium Channel BlockersAntiarrhythmicsVasodilator AgentsPharmaceuticalsAntianginal medicines |
| Siedepunkt | BP: 245 °C at 0.01 mm Hg243-246 °C at 1.00E-02 mm Hg586.1±50.0 °C(Predicted) |
| Decomposition | When heated to decomposition it emits toxic fumes of /nitrogen oxides and HCl/. |
| Schmelzpunkt | < 25 °C126-129°C |
| Brechungsindex | Index of refraction: 1.5448 at 25 °C |
| Physical Description | Solid |
| Stability/Shelf Life | Stable under recommended storage conditions. /Verapamil hydrochloride/Verapamil HCl should be stored at room temperature & protected from light. Infusion soln stability studies indicate that verapamil HCl does not adsorb to glass, PVC, or polyolefin containers. It is physically compatible in soln over a pH range of 3-6 but may precipitate in solns having a pH >6 or 7. |
| Dichte | 1.058±0.06 g/cm3(Predicted) |
| Lagerbedingungen | -20°C Freezer |
| pKa (Säurekonstante) | 8.97±0.50(Predicted) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]P261, P262, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P316, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 53 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H301: Toxic if swallowed [Danger Acute toxicity, oral] |
|---|---|
| Regulatorische Informationen | Verapamil: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - Benzeneacetonitrile, .alpha.-[3-[[2-(3,4-dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-.alpha.-(1-methylethyl)-: Environment tier I assessment |
| FDA-Anforderungen | The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including verapamil hydrochloride, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Verapamil hydrochloride/ |
| Special Reports | To report the presentation and controversies regarding therapy of an 18-year-old man following a life-threatening ingestion of verapamil. ... Treatment guidelines for critical care clinicians are provided. /salt not specified/ |
| Toxic Combustion Products | Special hazards arising from the substance or mixture: Carbon oxides, nitrogen oxides (NOx), hydrogen chloride gas. /Verapamil hydrochloride/ |
| Hazard Classes and Categories | Acute Tox. 3 (100%) |
| Hazardous Reactivities and Incompatibilities | Incompatible materials: Bases. /Verapamil hydrochloride/ |
| Brandbekämpfungsverfahren | Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. /Verapamil hydrochloride/Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary. /Verapamil hydrochloride/ |
Anwendungen & Verwendung
Verwenden
Both isomers inhibit the p-glycoprotein efflux pump in multidrug resistant tumor cells