Structure via PubChem · Public domain (PubChem)
noscapine
Sign in to saveAlso known as 6,7-dimethoxy-3-(4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-3H-isobenzofuran-1-one, (−)-α-narcotine, alpha-narcotine, (−)-noscapine
Noscapine, also known as narcotine, nectodon, nospen, anarcotine and (archaic) opiane, is a benzylisoquinoline alkaloid of the phthalideisoquinoline structural subgroup, which has been isolated from numerous species of the Papaveraceae (poppy) family. It lacks effects associated with opioids such as sedation, euphoria, or analgesia (pain-relief) and lacks addictive potential. Noscapine is primarily used for its antitussive (cough-suppressing) effects.
Key facts
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 408343932
- Drug.IUPAC_name
- (3S)-6,7-Dimethoxy-3-[(5R)-5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl]-1(3H)-isobenzofuranone
- Drug.image
- Noscapine Structure.svg
- Drug.image_class
- skin-invert-image
- Drug.image2
- Noscapine.png
- Drug.image_class2
- bg-transparent
- Drug.pregnancy_category
- Contraindicated
- Drug.legal_status
- Rx-only
- Drug.bioavailability
- ~30%
- Drug.elimination_half life
- 1.5–4 h (mean 2.5 h)
- Drug.CAS_number
- 128-62-1
- Drug.ATC_prefix
- R05
- Drug.ATC_suffix
- DA07
- Drug.PubChem
- 275196
- Drug.ChemSpiderID
- 242139
- Drug.UNII
- 8V32U4AOQU
via Wikipedia infobox
Chemical data
- Formula
- C22H23NO7
- Molecular weight
- 413.4 g/mol
- IUPAC name
- (3S)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3H-2-benzofuran-1-one
- SMILES
- CN1CCC2=CC3=C(C(=C2[C@@H]1[C@@H]4C5=C(C(=C(C=C5)OC)OC)C(=O)O4)OC)OCO3
- InChIKey
- AKNNEGZIBPJZJG-MSOLQXFVSA-N
- XLogP
- 2.7
- Polar surface area
- 75.7 Ų
- H-bond donors
- 0
- H-bond acceptors
- 8
- Formal charge
- 0
via PubChem
Research
744 papers- Noscapine and Apoptosis in Breast and Other Cancers.International journal of molecular sciences · 2024
- Noscapine comes of age.Phytochemistry · 2015
- Noscapine derivative 428 suppresses ferroptosis through targeting GPX4.Redox biology · 2025
- Noscapine, a Non-addictive Opioid and Microtubule-Inhibitor in Potential Treatment of Glioblastoma.Neurochemical research · 2019
- Synthesis and modification of noscapine derivatives as promising future anticancer agents.Bioorganic chemistry · 2024
via PubMed
Wikidata facts
- Mass
- 413.147
Show 5 more facts
- Commons category
- Noscapine
- isomeric SMILES
- C1N([C@@](C2=C(C1)C=C3OCOC3=C2OC)([H])[C@@]4(C=5C=CC(=C(C5C(O4)=O)OC)OC)[H])C
- chemical formula
- C₂₂H₂₃NO₇
- canonical SMILES
- CN1CCC2=CC3=C(C(=C2C1C4C5=C(C(=C(C=C5)OC)OC)C(=O)O4)OC)OCO3
- melting point
- 176
Sources (2)
via Wikidata · CC0
~11 min read
Article
17 sectionsContents
- Medical uses
- Side effects
- Interactions
- Biosynthesis
- Mechanism of action
- Structure analysis
- History
- Society and culture
- Recreational use
- Noscapine in heroin
- Research
- Clinical trials
- Noscapine biosynthesis reconstitution
- Anticancer derivatives
- Anti-inflammatory effects
- See also
- References
Noscapine, also known as narcotine, nectodon, nospen, anarcotine and (archaic) opiane, is a benzylisoquinoline alkaloid of the phthalideisoquinoline structural subgroup, which has been isolated from numerous species of the Papaveraceae (poppy) family. It lacks effects associated with opioids such as sedation, euphoria, or analgesia (pain-relief) and lacks addictive potential. Noscapine is primarily used for its antitussive (cough-suppressing) effects.
==Medical uses== Noscapine is often used as an antitussive medication. A 2012 Dutch guideline, however, does not recommend its use for acute coughing.