Papaverine

Base Information

• Chemical Name: Papaverine
• CAS No.: 58-74-2
• Molecular Formula: C20H21 N O4
• Molecular Weight: 339.391
• Hs Code.: 2933499090
• European Community (EC) Number: 200-397-2
• NSC Number: 136630
• UNII: DAA13NKG2Q
• DSSTox Substance ID: DTXSID4023418
• Nikkaji Number: J10.638K
• Wikipedia: Papaverine
• Wikidata: Q410374
• NCI Thesaurus Code: C726
• RXCUI: 7895
• Pharos Ligand ID: K6DDSGYUMMXB
• Metabolomics Workbench ID: 43340
• ChEMBL ID: CHEMBL19224
• Mol file: 58-74-2.mol

Synonyms:Cerespan;Hydrochloride, Papaverine;Papaverine;Papaverine Hydrochloride;Pavabid;Pavatym

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Chemical Property of Papaverine

Chemical Property:

• Melting Point: 226 °C
• Refractive Index: 1.6250 (estimate)
• Boiling Point: 483.2°Cat760mmHg
• PKA: 6.4(at 25℃)
• Flash Point: 172.2°C
• PSA: 49.81000
• Density: 1.161g/cm³
• LogP: 3.86000
• Solubility.: H2O: 25 mg/mL
• Water Solubility.: 37.33mg/L(37.5 oC)
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 339.14705815
• Heavy Atom Count: 25
• Complexity: 407

Purity/Quality:

Safty Information:

• Pictogram(s): Toxic narcotic.
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)CC2=NC=CC3=CC(=C(C=C32)OC)OC)OC
• Recent ClinicalTrials: Papaverine in Combination With Chemoradiation for the Treatment of Stage II-III Non-small Cell Lung Cancer
• Uses: Papaverine occurs in opium to the extent of0.8–1.0%, commonly associated with narcotine.It is used as a smooth muscle relaxantand in medicine for its vasodilator action onthe blood vessels in the brain. It is effectiveagainst asthma. folate metabolic inhibitor, coccidiostat opium alkaloid
• Indications: Papaverine (Pavabid) is a nonspecific phosphodiesterase inhibitor that increases cAMP and cGMP levels in penile erectile tissue. Papaverine is particularly known as a smooth muscle relaxant and vasodilator. Its principal pharmacological action is as a nonspecific vasodilator of smooth muscles of the arterioles and capillaries. Various vascular beds and smooth muscle respond differently to papaverine administration both in intensity and duration. Papaverine decreases the resistance to arterial inflow and increases the resistance to venous outflow.
• Therapeutic Function: Vasodilator, Platelet aggregation inhibitor
• Clinical Use: Papaverine is highly effective in men with psychogenic and neurogenic ED but less effective in men with vasculogenic ED. Papaverine–phentolamine combinations have been used in self-injection procedures. Papaverine doses may range from 15 to 60 mg. Papaverine treatment in patients with severe arterial or venous incompetence is usually unsuccessful, but autoinjections using low doses sufficient to achieve an erection are safe and efficient.

Technology Process of Papaverine

There total 76 articles about Papaverine 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: 98.0%

papaverine hydrochloride (61-25-6) → Papaverine (58-74-2)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1039/d1cc01756j

Reference yield: 94.0%

Bis[1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisochinolin-2-oxid] (33520-96-6) → Papaverine (58-74-2)

Guidance literature:

With ammonium chloride; zinc; In tetrahydrofuran; water; for 1h;

DOI:10.1016/j.tet.2008.12.004

Reference yield: 93.0%

papaverine hydrochloride → Papaverine (58-74-2)

Guidance literature:

With ammonium hydroxide;

DOI:10.3390/molecules24213938

upstream raw materials:

3,4-dihydropapaverine

papaveraldine

2-benzoyl-1-cyano-6,7-dimethoxy-1,2-dihydroisoquinoline

phenyllithium

Downstream raw materials:

papaverine ethiodide

papaverinol

Refernces

• 1、 Suau, Rafael,Rico-Gomez, Rodrigo,Souto-Bachiller, Fernando A.,Rodriguez-Rodriguez, Lolita de los,Ruiz, Manuel L.. "Efficient Photoinduced Electron Transfer in Papaverine N-Oxide: Regioselective Intramolecular Hydroxylation of Papaverine as an Alternative Disconnection for the Synthesis of Cularine Alkaloids". . p. 2653 - 2656. Retrieved 1995.
• 2、 Damayanti, Jeanne Dewi,Pratama, Dhanang Edy,Lee, Tu. "Green Technology for Salt Formation: Slurry Reactive Crystallization Studies for Papaverine HCl and 1:1 Haloperidol-Maleic Acid Salt". . p. 2881 - 2891. Retrieved 2019.
• 3、 Qiu, Zeng-Feng,Wu, Ze-Nong,Yang, Zhe-Zhou,Yu, Wen-Shuai,Zhang, Fu-Li,Zhao, Chun-Jie. "One-Pot Synthesis of Papaverine Hydrochloride and Identification of Impurities". . p. 1295 - 1299. Retrieved 2020/09/16.