1.0 2010-04-08 22:04:34 UTC 2019-11-26 02:54:49 UTC FDB000447 Papaverine Alkaloid from Papaver somniferum (opium poppy) Papaverine (pronounced /p??pæv?ri?n/) is an opium alkaloid used primarily in the treatment of visceral spasm, vasospasm (especially those involving the heart and the brain), and occasionally in the treatment of erectile dysfunction. While it is found in the opium poppy, papaverine differs in both structure and pharmacological action from the analgesic (morphine-related) opium alkaloids (opiates). In 1979, a Food and Drug Administration Advisory Committee evaluated studies on papaverine and concluded that there was a lack of objective data to support the therapeutic use of papaverine for these conditions. Papaverine remains available despite the committee's recommendation that it be withdrawn from the market.; Papaverine is a nonxanthine phosphodiesterase inhibitor for the relief of cerebral and peripheral ischemia associated with arterial spasm and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. 1-((3,4-Dimethoxyphenyl)methyl)-6,7-dimethoxyisoquinoline 1-(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-isoquinoline 1-(3,4-Dimethoxybenzyl)-6,7-dimethoxyisoquinoline 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxyisoquinoline 1-[(3,4-Dimethoxyphenyl)methyl]6,7-dimethoxyisoquinoline 4-[(6,7-Dimethoxyisoquinolyl)methyl]-1,2-dimethoxybenzene 58-74-2 (FREE BASE ) 6,7-Dimethoxy-1-(3,4-dimethoxybenzyl)isoquinoline 6,7-Dimethoxy-1-veratrylisoquinoline Ceraspan Cerespan Chlorhydrate de papaverine Isoquinoline, 6,7-dimethoxy-1-veratryl- Isoquinoline, 6,7-dimethoxy-1-veratryl- (8CI) Isoquinoline, 6,7-dimethoxy-1-veratryl-(8Cl) Mesotina NSC 35443 Papanerin Papanerine Papavarine chlorhydrate Papaverin Papaverina Papaverine [ban] Papaverine chlorohydrate Papaverine HCL Papaverine hydrochloride Papaverine monohydrochloride Papaverinium chloride Papaveroline tetramethyl ether Pavabid Pavacot Pavatym Robaxapap S-m-r C20H21NO4 339.385 339.147058165 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxyisoquinoline papaverine 61-25-6 COC1=C(OC)C=C(CC2=NC=CC3=CC(OC)=C(OC)C=C23)C=C1 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 XQYZDYMELSJDRZ-UHFFFAOYSA-N belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached. Benzylisoquinolines Organic compounds Organoheterocyclic compounds Isoquinolines and derivatives Benzylisoquinolines Aromatic heteropolycyclic compounds Alkyl aryl ethers Anisoles Azacyclic compounds Dimethoxybenzenes Heteroaromatic compounds Hydrocarbon derivatives Organonitrogen compounds Organopnictogen compounds Phenoxy compounds Pyridines and derivatives Alkyl aryl ether Anisole Aromatic heteropolycyclic compound Azacycle Benzenoid Benzylisoquinoline Dimethoxybenzene Ether Heteroaromatic compound Hydrocarbon derivative Methoxybenzene Monocyclic benzene moiety O-dimethoxybenzene Organic nitrogen compound Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Phenol ether Phenoxy compound Pyridine Isoquinoline alkaloids benzylisoquinoline alkaloid dimethoxybenzene isoquinolines Solid logp 4.19 ALOGPS logs -4.42 ALOGPS solubility 1.29e-02 g/l ALOGPS melting_point Mp 147-148° logp 3.08 ChemAxon pka_strongest_basic 6.03 ChemAxon iupac 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxyisoquinoline ChemAxon average_mass 339.385 ChemAxon mono_mass 339.147058165 ChemAxon smiles COC1=C(OC)C=C(CC2=NC=CC3=CC(OC)=C(OC)C=C23)C=C1 ChemAxon formula C20H21NO4 ChemAxon 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 ChemAxon inchikey XQYZDYMELSJDRZ-UHFFFAOYSA-N ChemAxon polar_surface_area 49.81 ChemAxon refractivity 95.52 ChemAxon polarizability 36.57 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 5 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 16315 Specdb::CMs 27349 Specdb::CMs 100234 Specdb::CMs 149141 Specdb::MsMs 42981 Specdb::MsMs 42982 Specdb::MsMs 42983 Specdb::MsMs 116385 Specdb::MsMs 116386 Specdb::MsMs 116387 Specdb::MsMs 449417 Specdb::MsMs 449418 Specdb::MsMs 449419 Specdb::MsMs 451833 Specdb::MsMs 452111 Specdb::MsMs 2226601 Specdb::MsMs 2227732 Specdb::MsMs 2228146 Specdb::MsMs 2229325 Specdb::MsMs 2230155 Specdb::MsMs 2231741 Specdb::MsMs 2232426 Specdb::MsMs 2234184 Specdb::MsMs 2244712 Specdb::MsMs 2245426 Specdb::MsMs 2246761 Specdb::MsMs 2252485 Specdb::MsMs 2253984 Specdb::MsMs 2254592 HMDB15245 EV1 #<Reference:0x000055ce319abfa0> #<Reference:0x000055ce319abde8> #<Reference:0x000055ce319abc30> Opium poppy Type 1 specific Papaver somniferum 3469 bitter