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Pseudaconitine

Names
Systematic IUPAC name 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)
Other names Nepaline; Acraconitine; Feraconitine; Pseudoaconitine; Nepal aconitine; Nepaline; Veratroylaconine
Identifiers
CAS Number	127-29-7
3D model (JSmol)	Interactive image
ChemSpider	390354
PubChem CID	441752
CompTox Dashboard (EPA)	DTXSID90894011
InChI InChI=1S/C36H51NO12/c1-9-37-16-33(17-42-3)23(39)13-24(45-6)36-20-14-34(41)25(46-7)15-35(49-18(2)38,27(30(36)37)28(47-8)29(33)36)26(20)31(34)48-32(40)19-10-11-21(43-4)22(12-19)44-5/h10-12,20,23-31,39,41H,9,13-17H2,1-8H3/t20-,23-,24+,25+,26-,27+,28+,29-,30?,31-,33+,34+,35-,36+/m1/s1Key: YVPYMQHYESYLIR-CERQHTHQSA-N InChI=1/C36H51NO12/c1-9-37-16-33(17-42-3)23(39)13-24(45-6)36-20-14-34(41)25(46-7)15-35(49-18(2)38,27(30(36)37)28(47-8)29(33)36)26(20)31(34)48-32(40)19-10-11-21(43-4)22(12-19)44-5/h10-12,20,23-31,39,41H,9,13-17H2,1-8H3/t20-,23-,24+,25+,26-,27+,28+,29-,30?,31-,33+,34+,35-,36+/m1/s1Key: YVPYMQHYESYLIR-CERQHTHQBX
SMILES O=C(O53(O)C416C2N(CC)C(1(OC)2(OC(=O)C)(C3OC)45)(COC)(O)C6OC)c7ccc(OC)c(OC)c7
Properties
Chemical formula	C26H51NO12
Molar mass	569.689 g·mol
Melting point	202 °C (396 °F; 475 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is  ?) Infobox references

Pseudaconitine, known also as nepaline, (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 belongs to the family Ranunculaceae. The plant is found in East Asia, including the Himalayas. The poison is in the roots of the plant.

Toxicity and mechanism

Pseudaconitine is a moderate inhibitor of the enzyme acetylcholinesterase. This enzyme breaks down the neurotransmitter acetylcholine through hydrolysis. 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.

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) is formed. This does not have the same tingling effect as pseudaconitine.

References

1. Aconitum ferox
2. Rahman, A, et al, New Norditerpenoid Alkoids from Aconitum falceroni, 2000
3. ^ Cash,J.T.,Dunstan,W.R., The Pharmacology of Pseudaconitine and Japaconitine considered in relation to that of Aconitine, 1901
4. Tsudaan Y., Marion L., Pseudaconitine, and the stereochemical relationship of the highly oxygenated aconite alkaloids, 1963

• Alkaloids
• Plant toxins
• Phenol ethers
• Acetate esters
• Benzoates