Drotaverine hydrochloride

Base Information

• Chemical Name: Drotaverine hydrochloride
• CAS No.: 985-12-6
• Deprecated CAS: 53908-09-1
• Molecular Formula: C₂₄H₃₁NO₄*ClH
• Molecular Weight: 433.975
• Hs Code.: 2933990090
• European Community (EC) Number: 619-357-4
• UNII: 24ZVH4C669
• DSSTox Substance ID: DTXSID40243590
• Wikidata: Q27253893
• NCI Thesaurus Code: C97980
• Mol file: 985-12-6.mol

Synonyms:dihydroisoperparine;drotaverin;drotaverin hydrochloride;drotaverine;isodihydroperparine;No-shpa;No-spa;Nospan;Nospanum

Chemical Property of Drotaverine hydrochloride

Chemical Property:

• Appearance/Colour: pale-yellow crystalline solid
• Vapor Pressure: 5E-14mmHg at 25°C
• Melting Point: 208-212 °C
• Boiling Point: 564oC at 760 mmHg
• Flash Point: 240.7oC
• PSA: 48.95000
• Density: 1.097 g/cm³
• LogP: 6.05600
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 433.2019862
• Heavy Atom Count: 30
• Complexity: 511

Purity/Quality:

99% ^*data from raw suppliers

DrotaverineHydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC1=C(C=C(C=C1)C=C2C3=CC(=C(C=C3CCN2)OCC)OCC)OCC.Cl
• Isomeric SMILES: CCOC1=C(C=C(C=C1)/C=C\2/C3=CC(=C(C=C3CCN2)OCC)OCC)OCC.Cl
• Recent ClinicalTrials: Drotaverine Hydrochloride Versus Hyoscine-N-butylbromide for Duodenal Antimotility During Endoscopic Retrograde Cholangiopancreatography (ERCP)
• Uses: Analogue of Papaverine. Antispasmodic A papaverine analog Analogue of Papaverine. Antispasmodic.

Technology Process of Drotaverine hydrochloride

There total 7 articles about Drotaverine hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.4%

N-(3,4-diethoxyphenylacetyl)-β-(3,4-diethoxyphenyl)ethylamine (6298-46-0) → 1-(3,4-diethoxybenzylidene)-6,7-diethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (985-12-6)

Guidance literature:

N-(3,4-diethoxyphenylacetyl)-β-(3,4-diethoxyphenyl)ethylamine; With trichlorophosphate; In toluene; at 40 - 90 ℃; Inert atmosphere;

With hydrogenchloride; In ethanol; water; for 0.5h; Inert atmosphere; Reflux;

Reference yield:

1,2-diethoxybenzene (2050-46-6) → 1-(3,4-diethoxybenzylidene)-6,7-diethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (985-12-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: zinc(II) chloride / dichloromethane / 1 h / 0 - 20 °C

2.1: sulfur; morpholine / 18 h / 110 - 120 °C

2.2: 8 h / 100 °C

3.1: 180 - 190 °C / Inert atmosphere

4.1: trichlorophosphate / toluene / 40 - 90 °C / Inert atmosphere

4.2: 0.5 h / Inert atmosphere; Reflux

With morpholine; sulfur; zinc(II) chloride; trichlorophosphate; In dichloromethane; toluene;

Reference yield:

ethyl 2-(3,4-diethoxyphenyl)-2-oxoacetate (53017-34-8) → 1-(3,4-diethoxybenzylidene)-6,7-diethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (985-12-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: hydrogenchloride; hydrogen; palladium 10% on activated carbon / ethanol / 15 h / 60 °C

2.1: sodium hydroxide; water / tetrahydrofuran / 50 - 60 °C

3.1: 180 - 190 °C / Inert atmosphere

4.1: trichlorophosphate / toluene / 40 - 90 °C / Inert atmosphere

4.2: 0.5 h / Inert atmosphere; Reflux

With hydrogenchloride; palladium 10% on activated carbon; water; hydrogen; sodium hydroxide; trichlorophosphate; In tetrahydrofuran; ethanol; toluene;

upstream raw materials:

1-(3,4-diethoxyphenyl)ethanone

2-(3,4-diethoxyphenyl)acetamide

1,2-diethoxybenzene

N-(3,4-diethoxyphenylacetyl)-β-(3,4-diethoxyphenyl)ethylamine

Refernces