brucine

Also 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 Å²
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

Mass: 394.189

Show 4 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
Commons category: Brucine

Sources (4)

via Wikidata · CC0

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