Structure via PubChem · Public domain (PubChem)
papaverine
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Papaverine (Latin papaver, "poppy") is an opium alkaloid antispasmodic drug, used primarily in the treatment of visceral spasms and vasospasms (especially those involving the intestines, heart, or brain), occasionally in the treatment of erectile dysfunction and acute mesenteric ischemia. While it is found in the opium poppy, papaverine differs in both structure and pharmacological action from the analgesic morphine and its derivatives (such as codeine).
Key facts
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 464197236
- Drug.IUPAC_name
- 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxyisoquinoline
- Drug.image
- Papaverine.svg
- Drug.image_class
- skin-invert-image
- Drug.image2
- Papaverine-from-xtal-3D-balls-B.png
- Drug.image_class2
- bg-transparent
- Drug.tradename
- Pavabid, others
- Drug.MedlinePlus
- a682707
- Drug.pregnancy_AU
- A
- Drug.pregnancy_US
- C
- Drug.legal_AU
- S4
- Drug.legal_US
- Rx-only
- Drug.routes_of_administration
- By mouth, intravenous, intramuscular, rectal, intracavernosal
- Drug.bioavailability
- 80%
- Drug.protein_bound
- ~90%
- Drug.metabolism
- Hepatic
via Wikipedia infobox
Chemical data
- Formula
- C20H21NO4
- Molecular weight
- 339.4 g/mol
- IUPAC name
- 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxyisoquinoline
- SMILES
- COC1=C(C=C(C=C1)CC2=NC=CC3=CC(=C(C=C32)OC)OC)OC
- InChIKey
- XQYZDYMELSJDRZ-UHFFFAOYSA-N
- XLogP
- 3.9
- Polar surface area
- 49.8 Ų
- H-bond donors
- 0
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 339.147
Show 4 more facts
- chemical formula
- C₂₀H₂₁NO₄
- canonical SMILES
- COC1=C(C=C(C=C1)CC2=NC=CC3=CC(=C(C=C32)OC)OC)OC
- Commons category
- Papaverine
- melting point
- 147
via Wikidata · CC0
~7 min read
Article
7 sectionsContents
- History
- Biosynthesis
- Uses
- Mechanism
- Side effects
- Formulations and trade names
- References
Papaverine (Latin papaver, "poppy") is an opium alkaloid antispasmodic drug, used primarily in the treatment of visceral spasms and vasospasms (especially those involving the intestines, heart, or brain), occasionally in the treatment of erectile dysfunction and acute mesenteric ischemia. While it is found in the opium poppy, papaverine differs in both structure and pharmacological action from the analgesic morphine and its derivatives (such as codeine).
In addition to opium, papaverine is purported to be present in high concentrations in star gooseberry.