Structure via PubChem · Public domain (PubChem)
brucine
Sign in to saveAlso known as 10,11-dimethoxy strychnine, brucin
Brucine is an alkaloid closely related to strychnine, most commonly found in the Strychnos nux-vomica tree. Brucine poisoning is rare, since it is usually ingested with strychnine, and strychnine is more toxic than brucine. In chemical synthesis, it can be used as a tool for stereospecific chemical syntheses.
Chemical data
- Formula
- C23H26N2O4
- Molecular weight
- 394.5 g/mol
- IUPAC name
- (4aR,5aS,8aR,13aS,15aS,15bR)-10,11-dimethoxy-4a,5,5a,7,8,13a,15,15a,15b,16-decahydro-2H-4,6-methanoindolo[3,2,1-ij]oxepino[2,3,4-de]pyrrolo[2,3-h]quinolin-14-one
- SMILES
- COC1=C(C=C2C(=C1)[C@]34CCN5[C@H]3C[C@@H]6[C@@H]7[C@@H]4N2C(=O)C[C@@H]7OCC=C6C5)OC
- InChIKey
- RRKTZKIUPZVBMF-IBTVXLQLSA-N
- XLogP
- 1
- Polar surface area
- 51.2 Ų
- H-bond donors
- 0
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Research
490 papers- Brucine: A Review of Phytochemistry, Pharmacology, and Toxicology.Frontiers in pharmacology · 2020
- Pharmacological investigation of brucine anti-ulcer potential.Frontiers in pharmacology · 2022
- Brucine restores sodium nitroprusside-induced chondrocyte dysfunction by suppressing the GSK-3β/β-catenin pathway.Chemico-biological interactions · 2022
- Brucine Inhibits Proliferation of Pancreatic Ductal Adenocarcinoma through PI3K/AKT Pathway-induced Mitochondrial Apoptosis.Current cancer drug targets · 2024
- Cyp3a11 metabolism-based chronotoxicity of brucine in mice.Toxicology letters · 2019
via PubMed
Wikidata facts
- Has part
- carbon
- Named after
- James Bruce
- Mass
- 394.189
Show 7 more facts
- chemical formula
- C₂₃H₂₆N₂O₄
- isomeric SMILES
- COC1=C(C=C2C(=C1)[C@]34CCN5[C@H]3C[C@@H]6[C@@H]7[C@@H]4N2C(=O)C[C@@H]7OCC=C6C5)OC
- canonical SMILES
- COC1=C(C=C2C(=C1)C34CCN5C3CC6C7C4N2C(=O)CC7OCC=C6C5)OC
- subject has role
- analgesic
- described by source
- Encyclopædia Britannica 11th edition
- different from
- brucite
- Commons category
- Brucine
via Wikidata · CC0
~4 min read
Encyclopedic overview
10 sectionsContents
- History
- Identification
- Applications
- Chemical applications
- Medical applications
- Alcohol denaturant
- Cultural references
- Safety
- References
- External links
Brucine is an alkaloid closely related to strychnine, most commonly found in the Strychnos nux-vomica tree. Brucine poisoning is rare, since it is usually ingested with strychnine, and strychnine is more toxic than brucine. In chemical synthesis, it can be used as a tool for stereospecific chemical syntheses.
Brucine's name derives from this of the genus Brucea, named after James Bruce who brought back Brucea antidysenterica from Ethiopia.
Excerpted from Wikipedia’s “brucine” article, available under the CC BY-SA 4.0 licence.