Pseudaconitine
| Pseudaconitine | |
|---|---|
| File:Pseudaconitine.png | |
| Other names 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) | |
| style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers | |
| CAS number | 127-29-7 |
| PubChem | 441752 |
| SMILES | Script error: No such module "collapsible list". |
| style="background: #F8EABA; text-align: center;" colspan="2" | Properties | |
| Molecular formula | C36H51NO12 |
| Molar mass | 689.79 g/mol |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| Infobox references | |
Pseudaconitine (C36H49NO12) is an alkaloid found in high quantities in the roots of Aconitum ferox also known as wolfsbane.
It is extremely poisonous.
Introduction
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 plant has long been known to botanists and travelers in India under the name "Bikh".
Sources
Pseudaconitine is produced by the plant Aconitum ferox, which belonts to the family Ranunculaceae. The plant is found in East Asia, including the Himalayas. The poison is in the roots of the plant. [1]
Toxicity and mechanism
Pseudaconitine is a moderate inhibitor of the enzyme acetylcholinesterase. This enzyme breaks down the neurotransmitter acetylcholine through hydrolysis.[2] Inhibition of this enzyme causes a constant stimulation of the postsynaptic membrane by the neurotransmitter which it cannot cancel. This accumulation of acetylcholine may thus lead to the constant stimulation of the muscles, glands and central nervous system. Furthermore, it appears the substance in small quantities also causes a tingling effect on the tongue, lips and skin.[3]
Structure and reactivity
Pseudaconitine is a diterpene alkaloid, with the structural formula C36H51NO12. The crystal melts at 202 °C and is moderately soluble in water, but more so in alcohol. This shows that it is a lipophilic substance. When heated in the dry state, it undergoes pseudaconitine pyrolysis and pyropseudaconitine (C34H47O10N) formed. This does not have the same tingling effect as pseudaconitine.[3][4]
References
Cite error: Invalid <references> tag;
parameter "group" is allowed only.
<references />, or <references group="..." />- ↑ Aconitum ferox
- ↑ Rahman, A, et al, New Norditerpenoid Alkoids from Aconitum falceroni, 2000
- ↑ 3.0 3.1 Cash,J.T.,Dunstan,W.R., The Pharmacology of Pseudaconitine and Japaconitine considered in relation to that of Aconitine, 1901
- ↑ Tsudaan Y., Marion L., Pseudaconitine, and the stereochemical relationship of the highly oxygenated aconite alkaloids, 1963
