Wikipedia

Pseudaconitine

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.

Pseudaconitine
Names
IUPAC name
8-(Acetyloxy)-20-ethyl-3,13-dihydroxy-1α,6α,16β-trimethoxy-4-(methoxymethyl)aconitan-14α-yl 3,4-dimethoxybenzoate
Other names
Nepaline; Acraconitine; Feraconitine; Pseudoaconitine; Nepal aconitine; Nepaline; Veratroylaconine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • 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/s1 checkY
    Key: YVPYMQHYESYLIR-CERQHTHQSA-N checkY
  • 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/s1
    Key: YVPYMQHYESYLIR-CERQHTHQBX
  • O=C(O[C@H]5[C@]3(O)C[C@H]4[C@@]16C2N(CC)C[C@]([C@H]1[C@@H](OC)[C@@H]2[C@@](OC(=O)C)(C[C@@H]3OC)[C@H]45)(COC)[C@H](O)C[C@@H]6OC)c7ccc(OC)c(OC)c7
Properties
C36H51NO12
Molar mass 689.799 g·mol−1
Melting point 202 °C (396 °F; 475 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

History

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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.[1]

Toxicity and mechanism

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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

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Pseudaconitine is a diterpene alkaloid, with the chemical 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 pyrolysis and pyropseudaconitine (C34H47O10N) is formed. This does not have the same tingling effect as pseudaconitine.[3][4]

See also

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References

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  1. ^ "Monkshood". AACC.org. Retrieved 9 November 2018.
  2. ^ Rahman, A, et al, New Norditerpenoid Alkoids from Aconitum falceroni, 2000
  3. ^ a b 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
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