Verapamil

Iupac Name：2-(3,4-dimethoxyphenyl)-5-[2-(3,4-dimethoxyphenyl)ethyl-methylamino]-2-propan-2-ylpentanenitrile

CAS No.: 52-53-9

Molecular Weight：454.60162

Modify Date.: 2022-11-06 13:04

Introduction: Verapamil, 5-[. Hemodynamically, verapamil causesa change in the preload, afterload, contractility, heart rate,and coronary blood flow. The drug reduces systemic vascularresistance and mean blood pressure, with minor effectson cardiac output.Verapamil is a synthetic compound possessing slightstructural similarity to papaverine. It can be separated intoits optically active isomers, of which the levorotatory enantiomeris the most potent. It is absorbed rapidly after oraladministration. The drug is metabolized quickly and, as aresult, has low bioavailability. The liver is the main siteof first-pass metabolism, forming several products. Thepreferential metabolic step involves N-dealkylation, followedby O-demethylation, and subsequent conjugation ofthe product before elimination. The metabolites have no significantbiological activity. Verapamil has an eliminationhalf-life of approximately 5 hours. View more+

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1. Names and Identifiers

1.1 Name: Verapamil
1.2 Synonyms: (±)-Verapamil 2-(3,4-Dimethoxyphenyl)-5-[[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino]-2-(propan-2-yl)pentanenitrile 2-(3,4-Dimethoxyphenyl)-5-[[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino]-2-isopropylpentanenitrile 2-(3,4-Dimethoxyphenyl)-5-[2-(3,4-dimethoxyphenyl)ethyl-methylamino]-2-propan-2-ylpentanenitrile -2-isopropyl- 2-isopropyl- 4-dimethoxy-alpha-(1-methylethyl)-l)- 5-((3,4-dimethoxyphenethyl)methylamino)-2-(3,4-dimethoxyphenyl)-2-isopropylv 5-[(3,4-Dimethoxyphenethyl)methylamino]-2-(3,4-dimethoxy phenyl)-2-isopropylvaleronitrile Benzeneacetonitrile, .alpha.-3-2-(3,4-dimethoxyphenyl)ethylmethylaminopropyl-3,4-dimethoxy-.alpha.-(1-methylethyl)- Benzeneacetonitrile, a-[3-[[2-(3,4-dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-a-(1-methylethyl)- (9CI) Benzeneacetonitrile, α-[3-[[2-(3,4-dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-α-(1-methylethyl)- CP 16533-1 D 365 dl-Verapamil Iproveratril Lekoptin NSC 272306NA R,S-Verapamil Valeronitrile, 5-[(3,4-dimethoxyphenethyl)methylamino]-2-(3,4-dimethoxyphenyl)-2-isopropyl- VPL α-[3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-α-(1-methylethyl)benzeneacetonitrile

1.3 CAS No.: 52-53-9

1.4 CID: 2520

1.5 EINECS(EC#): 200-145-1

1.6 Molecular Formula: C27H38N2O4 (isomer)

1.7 Inchi: InChI=1S/C27H38N2O4/c1-20(2)27(19-28,22-10-12-24(31-5)26(18-22)33-7)14-8-15-29(3)16-13-21-9-11-23(30-4)25(17-21)32-6/h9-12,17-18,20H,8,13-16H2,1-7H3

1.8 InChkey: SGTNSNPWRIOYBX-UHFFFAOYSA-N

1.9 Canonical Smiles: CC(C)C(CCCN(C)CCC1=CC(=C(C=C1)OC)OC)(C#N)C2=CC(=C(C=C2)OC)OC

1.10 Isomers Smiles: CC(C)C(CCCN(C)CCC1=CC(=C(C=C1)OC)OC)(C#N)C2=CC(=C(C=C2)OC)OC

2. Properties

2.1 Density: 1.058

2.1 Melting point: <25°C

2.1 Boiling point: 243-246℃ (1.3 Pa)

2.1 Refractive index: 1.5448

2.1 Flash Point: 308.3 °C

2.1 Precise Quality: 454.28300

2.1 PSA: 63.95000

2.1 logP: 5.09308

2.1 Appearance: Viscous, pale yellow oil.

2.2 Decomposition: When heated to decomposition it emits toxic fumes of /nitrogen oxides and HCl/.

2.3 pKa: 8.6(at 25℃)

2.4 Water Solubility: practically insoluble

2.5 Stability: Stable at normal temperatures and pressures.

2.6 StorageTemp: Keep in dark place,Inert atmosphere,Room temperature

3. Use and Manufacturing

3.1 Definition: ChEBI: A tertiary amino compound that is 3,4-dimethoxyphenylethylamine in which the hydrogens attached to the nitrogen are replaced by a methyl group and a 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl group.

3.2 General Description: Verapamil, 5-[. Hemodynamically, verapamil causesa change in the preload, afterload, contractility, heart rate,and coronary blood flow. The drug reduces systemic vascularresistance and mean blood pressure, with minor effectson cardiac output.Verapamil is a synthetic compound possessing slightstructural similarity to papaverine. It can be separated intoits optically active isomers, of which the levorotatory enantiomeris the most potent. It is absorbed rapidly after oraladministration. The drug is metabolized quickly and, as aresult, has low bioavailability. The liver is the main siteof first-pass metabolism, forming several products. Thepreferential metabolic step involves N-dealkylation, followedby O-demethylation, and subsequent conjugation ofthe product before elimination. The metabolites have no significantbiological activity. Verapamil has an eliminationhalf-life of approximately 5 hours.

3.3 Usage: Vasodilator (coronary).

4. Safety and Handling

4.1 Hazard Codes: C

4.1 Hazard Class: 8

4.1 WGK Germany: 3

4.1 Safety: A poison by ingestion, subcutaneous, intraperitoneal, and intravenous routes. When heated to decomposition it emits toxic fumes of NOx and CN−. See also NITRILES.

4.2 Toxicity: LD50 oral in rat: 163mg/kg

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 3

Acute toxicity - Dermal, Category 3

Acute toxicity - Inhalation, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H301 Toxic if swallowed H311 Toxic in contact with skin H331 Toxic if inhaled
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026 P321 Specific treatment (see ... on this label). P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P312 Call a POISON CENTER/doctor/\u2026if you feel unwell. P361+P364 Take off immediately all contaminated clothing and wash it before reuse. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P311 Call a POISON CENTER/doctor/\u2026
Storage	P405 Store locked up. P403+P233 Store in a well-ventilated place. Keep container tightly closed.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

Mass spectrum (electron ionization)

7. Synthesis Route

52-53-9Total: 3 Synthesis Route

625-28-5 11 Suppliers

52-53-9 69 Suppliers

Literatures:
Wu, Lingyun; Hartwig, John F. Journal of the American Chemical Society, 2005 , vol. 127, # 45 p. 15824 - 15832
Yield: null

128776-24-9

52-53-9 69 Suppliers

Literatures:
Wu, Lingyun; Hartwig, John F. Journal of the American Chemical Society, 2005 , vol. 127, # 45 p. 15824 - 15832
Yield: null

871703-17-2

3490-06-0 19 Suppliers

52-53-9 69 Suppliers

Literatures:
Wu, Lingyun; Hartwig, John F. Journal of the American Chemical Society, 2005 , vol. 127, # 45 p. 15824 - 15832
Yield: ~80%

8. Precursor and Product

precursor:

3490-06-0

128776-24-9

625-28-5

871703-17-2

product :

36622-29-4

67018-85-3

38321-02-7

34245-14-2

27487-66-7

71539-08-7

9. Computational chemical data

Molecular Weight: 454.60162g/mol
Molecular Formula: C₂₇H₃₈N₂O₄
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 454.28315770
Monoisotopic Mass: 454.28315770
Complexity: 606
Rotatable Bond Count: 13
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 6
Topological Polar Surface Area: 64
Heavy Atom Count: 33
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 1
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcfB7OAAAAAAAAAAAAAAAAAAAAAAAAAAwYAAAAAAAAAABQAAAHgAAAAAADwTBmAYyBoMABACQBiBCAAACCAAgIAAIiAAOiIgNpiKEsRuEMCIkwBGKqA+Q0PIPoAABAAAAQABAAAIAAACAAAAAAAAAAA==

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