Structure via PubChem · Public domain (PubChem)
aconitine
Sign in to saveAlso known as 16-Ethyl-1alpha,6alpha,19beta-trimethoxy-4-(methoxymethyl)-aconitane-3alpha,8,10alpha,11,18alpha-pentol, 8-acetate 10-benzoate
Chemical data
- Formula
- C34H47NO11
- Molecular weight
- 645.7 g/mol
- IUPAC name
- [(1S,2R,3R,4R,5R,6S,7S,8R,9R,13R,14R,16S,17S,18R)-8-acetyloxy-11-ethyl-5,7,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-yl] benzoate
- SMILES
- CCN1C[C@@]2([C@@H](C[C@@H]([C@@]34[C@@H]2[C@H]([C@@H](C31)[C@@]5([C@@H]6[C@H]4C[C@@]([C@@H]6OC(=O)C7=CC=CC=C7)([C@H]([C@@H]5O)OC)O)OC(=O)C)OC)OC)O)COC
- InChIKey
- XFSBVAOIAHNAPC-XTHSEXKGSA-N
- XLogP
- 0.3
- Polar surface area
- 153 Ų
- H-bond donors
- 3
- H-bond acceptors
- 12
- Formal charge
- 0
via PubChem
Research
2,351 papers- Aconitine: A review of its pharmacokinetics, pharmacology, toxicology and detoxification.Journal of ethnopharmacology · 2022
- Aconitine in Synergistic, Additive and Antagonistic Approaches.Toxins · 2024
- Aconitine poisoning due to Chinese herbal medicines: a review.Veterinary and human toxicology · 1994
- Aconitine-induced cardiac arrhythmia.British heart journal · 1958
- Cardiac efficacy and toxicity of aconitine: A new frontier for the ancient poison.Medicinal research reviews · 2021
via PubMed
Wikidata facts
- Has part
- carbon
- Mass
- 645.314911
Show 8 more facts
- Commons category
- Aconitine
- chemical formula
- C₃₄H₄₇NO₁₁
- canonical SMILES
- CCN1CC2(C(CC(C34C2C(C(C31)C5(C6C4CC(C6OC(=O)C7=CC=CC=C7)(C(C5O)OC)O)OC(=O)C)OC)OC)O)COC
- isomeric SMILES
- CCN1C[C@@]2([C@@H](C[C@@H]([C@@]34[C@@H]2[C@H]([C@@H](C31)[C@@]5([C@@H]6[C@H]4C[C@@]([C@@H]6OC(=O)C7=CC=CC=C7)([C@H]([C@@H]5O)OC)O)OC(=O)C)OC)OC)O)COC
- subject has role
- toxin
- found in taxon
- Aconitum fischeri
- different from
- Aconitase
- melting point
- 202.5
via Wikidata · CC0
~12 min read
Encyclopedic overview
12 sectionsContents
- Structure and reactivity
- Mechanism of action
- Biosynthesis and total synthesis of related alkaloids
- Metabolism
- Uses
- Toxicity
- Diagnosis and treatment
- Famous poisonings
- In popular culture
- See also
- References
- External links
Aconitine is an alkaloid toxin produced by various plant species belonging to the genus Aconitum (family Ranunculaceae), commonly known by the names wolfsbane and monkshood. Aconitine is notorious for its toxic properties.
==Structure and reactivity== Biologically active isolates from Aconitum and Delphinium plants are classified as norditerpenoid alkaloids, which are further subdivided based on the presence or absence of the C18 carbon. Aconitine is a C19-norditerpenoid, based on its presence of this C18 carbon. It is barely soluble in water, but very soluble in organic solvents such as chloroform or diethyl ether. Aconitine is also soluble in mixtures of alcohol and water if the concentration of alcohol is high enough.
Excerpted from Wikipedia’s “aconitine” article, available under the CC BY-SA 4.0 licence.