Showing Compound Papaverine (FDB000447)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:34 UTC

Update date

2019-11-26 02:54:49 UTC

Primary ID

FDB000447

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Papaverine

Description

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 Papaverine remains available despite the committee's recommendation that it be withdrawn from the market.; Papaverine is a nonxanthine phosphodiesterase inhibitor for the relief of cerebral and peripheral ischemia associated with arterial spasm and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.

CAS Number

61-25-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
1-((3,4-Dimethoxyphenyl)methyl)-6,7-dimethoxyisoquinoline	biospider
1-(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-isoquinoline	biospider
1-(3,4-Dimethoxybenzyl)-6,7-dimethoxyisoquinoline	biospider
1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxyisoquinoline	biospider
1-[(3,4-Dimethoxyphenyl)methyl]6,7-dimethoxyisoquinoline	biospider
4-[(6,7-Dimethoxyisoquinolyl)methyl]-1,2-dimethoxybenzene	biospider
58-74-2 (FREE BASE )	biospider
6,7-Dimethoxy-1-(3,4-dimethoxybenzyl)isoquinoline	db_source
6,7-Dimethoxy-1-veratrylisoquinoline	biospider
Ceraspan	biospider

Showing 1 to 10 of 35 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.013 g/L	ALOGPS
logP	4.19	ALOGPS
logP	3.08	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	6.03	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	49.81 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	95.52 m³·mol⁻¹	ChemAxon
Polarizability	36.57 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C20H21NO4

IUPAC name

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

InChI Identifier

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

InChI Key

XQYZDYMELSJDRZ-UHFFFAOYSA-N

Isomeric SMILES

COC1=C(OC)C=C(CC2=NC=CC3=CC(OC)=C(OC)C=C23)C=C1

Average Molecular Weight

339.385

Monoisotopic Molecular Weight

339.147058165

Classification

Description

Belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoquinolines and derivatives

Sub Class

Benzylisoquinolines

Direct Parent

Benzylisoquinolines

Alternative Parents

Substituents

Benzylisoquinoline
O-dimethoxybenzene
Dimethoxybenzene
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Alkyl aryl ether
Monocyclic benzene moiety
Pyridine
Benzenoid
Heteroaromatic compound
Ether
Azacycle
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzylisoquinoline alkaloid (CHEBI:28241 )
dimethoxybenzene (CHEBI:28241 )
isoquinolines (CHEBI:28241 )
Isoquinoline alkaloids (C06533 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Biofluid and excreta:

Role

Industrial application:

Drug

Pharmaceutical industry:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	2.95	AVDEEF,A (1997)
Experimental pKa	pKa 6.4 (25°)	DFC
Experimental Water Solubility	0.035 mg/mL at 17 oC	BEILSTEIN
Isoelectric point	Not Available
Mass Composition	C 70.78%; H 6.24%; N 4.13%; O 18.86%	DFC
Melting Point	Mp 147-148°	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Papaverine, non-derivatized, GC-MS Spectrum	splash10-0079-4569000000-42d74df972bf1280fb29	Spectrum
GC-MS	Papaverine, non-derivatized, GC-MS Spectrum	splash10-0079-4569000000-42d74df972bf1280fb29	Spectrum
Predicted GC-MS	Papaverine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05fs-0279000000-6a8c8886127d693c8567	Spectrum
Predicted GC-MS	Papaverine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0006-0009000000-376bdab66f9ada8143f2	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0f6x-0049000000-fbf8945b1b40a8e629ff	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00di-0779000000-37837168aff5cb2db6db	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-0006-0019000000-175d5d7601656bade9be	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-00dl-0569000000-1f7e7c97dcea64bf274a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0029000000-453bc4f2053e78c8ce45	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0ac0-0941000000-5b8b44adc1288a93aee5	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0ac0-0951000000-bb231dbbbd59dcf69c8f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0006-0029000000-8bc67120d4b4d28737dc	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0fk9-0279000000-6ce87da6708962b5e939	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0fk9-0279000000-c73bc5d2d851aa9cafe7	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0009000000-f4615816604a967ae786	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0ab9-0951000000-c9eb047b22f953796620	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0f6x-0049000000-fbf8945b1b40a8e629ff	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0009000000-a69cf627410b83b67bd3	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-00di-0779000000-37837168aff5cb2db6db	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0fdo-0249000000-cee8c55509567c9c6d6c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0029000000-70b62b3d039f4e99bf22	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0fk9-0379000000-7a3c6f8ee88d8001e5be	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0009000000-5adf8eed4c99ef024ca8	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0009000000-90f688022df6ca82e68d	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f6x-0092000000-d2012c62f8a18f28d8e0	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-14a648b12b81f2d898df	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0019000000-3f207d6944b0d0c476ad	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0gbc-0090000000-218cfc775f1db8beaf69	2016-08-03	View Spectrum