Structure via PubChem · Public domain (PubChem)
glaucine
Sign in to saveAlso known as (+)-glaucine
Glaucine (also known as 1,2,9,10-tetramethoxyaporphine, bromcholitin, glauvent, tusidil, and tussiglaucin) is an aporphine alkaloid found in several different plant species in the family Papaveraceae, such as Glaucium flavum, Glaucium oxylobum, and Corydalis yanhusuo, and in other plants such as Croton lechleri in the family Euphorbiaceae.
Chemical data
- Formula
- C21H25NO4
- Molecular weight
- 355.4 g/mol
- IUPAC name
- (6aS)-1,2,9,10-tetramethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline
- SMILES
- CN1CCC2=CC(=C(C3=C2[C@@H]1CC4=CC(=C(C=C43)OC)OC)OC)OC
- InChIKey
- RUZIUYOSRDWYQF-HNNXBMFYSA-N
- XLogP
- 3.4
- Polar surface area
- 40.2 Ų
- H-bond donors
- 0
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
169 papers- Glaucine inhibits hypoxia-induced angiogenesis and attenuates LPS-induced inflammation in human retinal pigment epithelial ARPE-19 cells.European journal of pharmacology · 2024
- Pharmacokinetics of glaucine after intravenous and oral administrations and detection of systemic aporphine alkaloids after ingestion of tulip poplar shavings in horses.Journal of veterinary pharmacology and therapeutics · 2022
- Glaucine inhibits breast cancer cell migration and invasion by inhibiting MMP-9 gene expression through the suppression of NF-κB activation.Molecular and cellular biochemistry · 2015
- Study of the in vivo and in vitro cardiovascular effects of (+)-glaucine and N-carbethoxysecoglaucine in rats.British journal of pharmacology · 1995
- Bronchodilator and anti-inflammatory activities of glaucine: In vitro studies in human airway smooth muscle and polymorphonuclear leukocytes.British journal of pharmacology · 1999
via PubMed
Wikidata facts
- Mass
- 355.178
Show 6 more facts
- found in taxon
- Corydalis cava
- chemical formula
- C₂₁H₂₅NO₄
- canonical SMILES
- CN1CCC2=CC(=C(C3=C2C1CC4=CC(=C(C=C43)OC)OC)OC)OC
- isomeric SMILES
- CN1CCC2=CC(=C(C3=C2[C@@H]1CC4=CC(=C(C=C43)OC)OC)OC)OC
- subject has role
- parasympatholytic
- Commons category
- Glaucine
Sources (2)
via Wikidata · CC0
~5 min read
Encyclopedic overview
8 sectionsContents
- Chemistry
- Stereoisomerism
- Mechanism of action
- Uses
- Medical
- Recreational
- See also
- References
Glaucine (also known as 1,2,9,10-tetramethoxyaporphine, bromcholitin, glauvent, tusidil, and tussiglaucin) is an aporphine alkaloid found in several different plant species in the family Papaveraceae, such as Glaucium flavum, Glaucium oxylobum, and Corydalis yanhusuo, and in other plants such as Croton lechleri in the family Euphorbiaceae.
It has bronchodilator, neuroleptic and antiinflammatory effects, acting as a PDE4 inhibitor and calcium channel blocker, and is used medically as an antitussive in some countries. TLRs plays role in its anti inflammatory effects. Glaucine may produce side effects such as sedation, fatigue, and a hallucinogenic effect characterised by colourful visual images, and has been detected as a novel psychoactive drug. In 2019, its isomer (R)-glaucine is reported to be a positive allosteric modulator of the 5-HT2A receptor, which is also associated with the hallucinogenic effects of substances such as psilocybin and mescaline.
Excerpted from Wikipedia’s “glaucine” article, available under the CC BY-SA 4.0 licence.