1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxyisoquinoline

• ChemBase ID: 984
• Molecular Formular: C20H21NO4
• Molecular Mass: 339.38504
• Monoisotopic Mass: 339.14705816
• SMILES: O(c1cc2c(nccc2cc1OC)Cc1cc(OC)c(OC)cc1)C
• Canonical SMILES: COc1ccc(cc1OC)Cc1nccc2c1cc(OC)c(c2)OC
• InChI: InChI=1S/C20H21NO4/c1-22-17-6-5-13(10-18(17)23-2)9-16-15-12-20(25-4)19(24-3)11-14(15)7-8-21-16/h5-8,10-12H,9H2,1-4H3
• InChIKey: XQYZDYMELSJDRZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxyisoquinoline
• IUPAC Traditional name: papaverine
• Brand Name: Alapav; Artegodan; Cardiospan; Cardoverina; Cepaverin; Cerebid; Cerespan; Delapav; Dilaves; Dispamil; Drapavel; Durapav; Dynovas; Forpavin; Genabid; Myobid; Optenyl; Pameion; Pamelon; Panergon; Pap H; Papacon; Papalease; Papanerin; Papanerin-Hcl; Papanerine; Papaversan; Papital T.R.; Paptial T.R.; Pavabid; Pavabid Hp; Pavacap; Pavacels; Pavacen; Pavacot; Pavadel; Pavagen; Pavakey; Pavarine; Pavased; Pavatest; Pavatine; Pavatym; Paverolan; Paveron; Pavnell; Qua Bid; Ro-Papav; Robaxapap; Spasmo-Nit; Therapav; Vasal; Vaso-Pav
• Synonyms: Chlorhydrate de Papaverine; Papavarine Chlorhydrate; Papaverine Chlorohydrate; Papaverine Hcl; Papaverine Hydrochloride; Papaverine Monohydrochloride; Papaverinium Chloride; Papaverin; Papaverine; Papaverine; 1-(3,4-DIMETHOXYBENZYL)-6,7-DIMETHOXYISOQUINOLINE; 罂粟碱

Database IDs

• CAS Number: 58-74-2; 61-25-6
• EC Number: 200-397-2
• MDL Number: MFCD00024138
• Beilstein Number: 312930
• Merck Index: 147019
• PubChem SID: 46508003; 160964447
• PubChem CID: 4680

CALCULATED PROPERTIES

JChem

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 2.4896507
• LogD (pH = 7.4): 3.062748
• Log P: 3.080075
• Molar Refractivity: 95.5175 cm^3
• Polarizability: 38.36705 Å^3
• Polar Surface Area: 49.81 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.19
• LOG S: -4.42
• Solubility (Water): 1.29e-02 g/l

PROPERTIES

Physical Property

• Melting Point: 146-147°C
• Hydrophobicity(logP): 3

Safety Information

• Storage Warning: Light Sensitive
• RTECS: NW8450000
• European Hazard Symbols: X
• Risk Statements: 22
• Safety Statements: 2-22
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H302
• GHS Precautionary statements: P264-P270-P301+P312-P330-P501A

Product Information

• Purity: 97%

DETAILS

DrugBank - DB01113

• Drug Groups: approved
• Description: An alkaloid found in opium but not closely related to the other opium alkaloids in its structure or pharmacological actions. It is a direct-acting smooth muscle relaxant used in the treatment of impotence and as a vasodilator, especially for cerebral vasodilation. The mechanism of its pharmacological actions is not clear, but it apparently can inhibit phosphodiesterases and it may have direct actions on calcium channels. [PubChem]
• Indication: For the treatment of impotence and vasospasms.
• Pharmacology: Papaverine is a nonxanthine phosphodiesterase inhibitor for the relief of cerebral and peripheral ischemia associated with arterial spasm and myocardial ischemia complicated by arrhythmias. The main actions of Papaverine are exerted on cardiac and smooth muscle. Like qathidine, Papaverine acts directly on the heart muscle to depress conduction and prolong the refractory period. Papaverine relaxes various smooth muscles. This relaxation may be prominent if spasm exists. The muscle cell is not paralyzed by Papaverine and still responds to drugs and other stimuli causing contraction. The antispasmodic effect is a direct one, and unrelated to muscle innervation. Papaverine is practically devoid of effects on the central nervous system. Papaverine relaxes the smooth musculature of the larger blood vessels, especially coronary, systemic peripheral, and pulmonary arteries.
• Affected Organisms: Humans and other mammals
• Half Life: 0.5-2 hours
• Protein Binding: ~90%
• References: Tang Y, Luan J, Zhang X: Accelerating tissue expansion by application of topical papaverine cream. Plast Reconstr Surg. 2004 Oct;114(5):1166-9. [Pubmed] ; Liu JK, Couldwell WT: Intra-arterial papaverine infusions for the treatment of cerebral vasospasm induced by aneurysmal subarachnoid hemorrhage. Neurocrit Care. 2005;2(2):124-32. [Pubmed] ; Takeuchi K, Sakamoto S, Nagayoshi Y, Nishizawa H, Matsubara J: Reactivity of the human internal thoracic artery to vasodilators in coronary artery bypass grafting. Eur J Cardiothorac Surg. 2004 Nov;26(5):956-9. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

DrugBank - DB07725

Drug information: experimental

REFERENCES

• Tang Y, Luan J, Zhang X: Accelerating tissue expansion by application of topical papaverine cream. Plast Reconstr Surg. 2004 Oct;114(5):1166-9. Pubmed
• Liu JK, Couldwell WT: Intra-arterial papaverine infusions for the treatment of cerebral vasospasm induced by aneurysmal subarachnoid hemorrhage. Neurocrit Care. 2005;2(2):124-32. Pubmed
• Takeuchi K, Sakamoto S, Nagayoshi Y, Nishizawa H, Matsubara J: Reactivity of the human internal thoracic artery to vasodilators in coronary artery bypass grafting. Eur J Cardiothorac Surg. 2004 Nov;26(5):956-9. Pubmed