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Showing Compound Papaverine (FDB000447)

Record Information
Version1.0
Creation date2010-04-08 22:04:34 UTC
Update date2019-11-26 02:54:49 UTC
Primary IDFDB000447
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePapaverine
DescriptionAlkaloid 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 Papaverine remains available despite the committee's recommendation that it be withdrawn from the market.; Papaverine is a nonxanthine phosphodiesterase inhibitor for the relief of cerebral and peripheral ischemia associated with arterial spasm and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 Number61-25-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
MesotinaKegg
Chlorhydrate de papaverineHMDB
Papavarine chlorhydrateHMDB
PapaverinHMDB
Papaverine chlorohydrateHMDB
Papaverine monohydrochlorideHMDB
Papaverinium chlorideHMDB
CerespanMeSH, HMDB
Hydrochloride, papaverineMeSH, HMDB
PavatymMeSH, HMDB
PavabidMeSH, HMDB
Papaverine hydrochlorideMeSH, HMDB
1-((3,4-Dimethoxyphenyl)methyl)-6,7-dimethoxyisoquinolinebiospider
1-(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-isoquinolinebiospider
1-(3,4-Dimethoxybenzyl)-6,7-dimethoxyisoquinolinebiospider
1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxyisoquinolinebiospider
1-[(3,4-Dimethoxyphenyl)methyl]6,7-dimethoxyisoquinolinebiospider
4-[(6,7-Dimethoxyisoquinolyl)methyl]-1,2-dimethoxybenzenebiospider
58-74-2 (FREE BASE )biospider
6,7-Dimethoxy-1-(3,4-dimethoxybenzyl)isoquinolinedb_source
6,7-Dimethoxy-1-veratrylisoquinolinebiospider
Ceraspanbiospider
Isoquinoline, 6,7-dimethoxy-1-veratryl-biospider
Isoquinoline, 6,7-dimethoxy-1-veratryl- (8CI)biospider
Isoquinoline, 6,7-dimethoxy-1-veratryl-(8Cl)biospider
NSC 35443db_source
Papanerinbiospider
Papanerinebiospider
Papaverinabiospider
Papaverine [ban]biospider
Papaverine HCLbiospider
Papaveroline tetramethyl etherdb_source
Pavacotbiospider
Robaxapapbiospider
S-m-rbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
logP4.19ALOGPS
logP3.08ChemAxon
logS-4.4ALOGPS
pKa (Strongest Basic)6.03ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area49.81 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity95.52 m³·mol⁻¹ChemAxon
Polarizability36.57 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H21NO4
IUPAC name1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxyisoquinoline
InChI IdentifierInChI=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 KeyXQYZDYMELSJDRZ-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(OC)C=C(CC2=NC=CC3=CC(OC)=C(OC)C=C23)C=C1
Average Molecular Weight339.385
Monoisotopic Molecular Weight339.147058165
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIsoquinolines and derivatives
Sub ClassBenzylisoquinolines
Direct ParentBenzylisoquinolines
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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 70.78%; H 6.24%; N 4.13%; O 18.86%DFC
Melting PointMp 147-148°DFC
Boiling PointNot Available
Experimental Water Solubility0.035 mg/mL at 17 oCBEILSTEIN
Experimental logP2.95AVDEEF,A (1997)
Experimental pKapKa 6.4 (25°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data327 (e 4660) (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSPapaverine, non-derivatized, GC-MS Spectrumsplash10-0079-4569000000-42d74df972bf1280fb29Spectrum
GC-MSPapaverine, non-derivatized, GC-MS Spectrumsplash10-0079-4569000000-42d74df972bf1280fb29Spectrum
Predicted GC-MSPapaverine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05fs-0279000000-6a8c8886127d693c8567Spectrum
Predicted GC-MSPapaverine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-0009000000-376bdab66f9ada8143f22017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0f6x-0049000000-fbf8945b1b40a8e629ff2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0779000000-37837168aff5cb2db6db2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0006-0019000000-175d5d7601656bade9be2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-00dl-0569000000-1f7e7c97dcea64bf274a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-0029000000-453bc4f2053e78c8ce452021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0ac0-0941000000-5b8b44adc1288a93aee52021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0ac0-0951000000-bb231dbbbd59dcf69c8f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0006-0029000000-8bc67120d4b4d28737dc2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0fk9-0279000000-6ce87da6708962b5e9392021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0fk9-0279000000-c73bc5d2d851aa9cafe72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-f4615816604a967ae7862021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0ab9-0951000000-c9eb047b22f9537966202021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0f6x-0049000000-fbf8945b1b40a8e629ff2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-a69cf627410b83b67bd32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-00di-0779000000-37837168aff5cb2db6db2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0fdo-0249000000-cee8c55509567c9c6d6c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-0029000000-70b62b3d039f4e99bf222021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0fk9-0379000000-7a3c6f8ee88d8001e5be2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-5adf8eed4c99ef024ca82016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0009000000-90f688022df6ca82e68d2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-0092000000-d2012c62f8a18f28d8e02016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-14a648b12b81f2d898df2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0019000000-3f207d6944b0d0c476ad2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gbc-0090000000-218cfc775f1db8beaf692016-08-03View Spectrum
NMRNot Available
ChemSpider ID4518
ChEMBL IDCHEMBL19224
KEGG Compound IDC06533
Pubchem Compound ID4680
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB01113
HMDB IDHMDB15245
CRC / DFC (Dictionary of Food Compounds) IDBCK58-R:BCK58-R
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00001899
HET IDEV1
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDPapaverine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.