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Pseudoaconitine
Sign in to saveAlso known as 1α,6α,14α(E),16β-20-Ethyl-1,6,16-trimethoxy-4-methoxymethyl-3,13-dihydroxyaconitane-8,14-diyl 8-acetate 14-(3,4-dimethoxybenzoate)
Pseudaconitine, also known as nepaline (C36H51NO12), is an extremely toxic alkaloid found in high quantities in the roots of Aconitum ferox, also known as Indian Monkshood, which belongs to the family Ranunculaceae. The plant is found in East Asia, including the Himalayas.
Chemical data
- Formula
- C36H51NO12
- Molecular weight
- 689.8 g/mol
- IUPAC name
- [(1S,2R,3R,4R,5S,6S,8R,9R,10R,13R,14R,16S,17S,18R)-8-acetyloxy-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-yl] 3,4-dimethoxybenzoate
- SMILES
- CCN1C[C@@]2([C@@H](C[C@@H]([C@@]34[C@@H]2[C@H]([C@@H]([C@H]31)[C@]5(C[C@@H]([C@]6(C[C@@H]4[C@@H]5[C@H]6OC(=O)C7=CC(=C(C=C7)OC)OC)O)OC)OC(=O)C)OC)OC)O)COC
- InChIKey
- YVPYMQHYESYLIR-HZKWNRCISA-N
- XLogP
- 1.2
- Polar surface area
- 152 Ų
- H-bond donors
- 2
- H-bond acceptors
- 13
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 689.341
Show 3 more facts
- isomeric SMILES
- CCN1C[C@@]2([C@@H](C[C@@H]([C@@]34[C@@H]2[C@H]([C@@H]([C@H]31)[C@]5(C[C@@H]([C@]6(C[C@@H]4[C@@H]5[C@H]6OC(=O)C7=CC(=C(C=C7)OC)OC)O)OC)OC(=O)C)OC)OC)O)COC
- canonical SMILES
- CCN1CC2(C(CC(C34C2C(C(C31)C5(CC(C6(CC4C5C6OC(=O)C7=CC(=C(C=C7)OC)OC)O)OC)OC(=O)C)OC)OC)O)COC
- chemical formula
- C₃₆H₅₁NO₁₂
Sources (1)
via Wikidata · CC0
~2 min read
Encyclopedic overview
5 sectionsContents
- History
- Toxicity and mechanism
- Structure and reactivity
- See also
- References
Pseudaconitine, also known as nepaline (C36H51NO12), is an extremely toxic alkaloid found in high quantities in the roots of Aconitum ferox, also known as Indian Monkshood, which belongs to the family Ranunculaceae. The plant is found in East Asia, including the Himalayas.
== History == Pseudaconitine was discovered in 1878 by Wright and Luff. They isolated a highly toxic alkaloid from the roots of the plant Aconitum ferox and called it pseudaconitine. The poison is also called bikh, bish, or nabee.
Excerpted from Wikipedia’s “Pseudoaconitine” article, available under the CC BY-SA 4.0 licence.
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