Pseudaconitine

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Pseudaconitine
Pseudaconitine.svg
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
PubChem CID
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 Yes check.svgY
    Key: YVPYMQHYESYLIR-CERQHTHQSA-N Yes check.svgY
  • 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).
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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.

Contents

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. [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 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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<i>Aconitum ferox</i> Species of plant

Aconitum ferox is a member of the monkshood genus Aconitum of the Ranunculaceae. The common name by which it is most often known in English is Indian Aconite, while the Hindi names used by practitioners of Ayurveda include वत्सनाभvatsanabha and महाविषाmahavisha.

<i>Aconitum lycoctonum</i> Species of plant

Aconitum lycoctonum is a species of flowering plant in the genus Aconitum, of the family Ranunculaceae, native to much of Europe and northern Asia. It is found in lowlands to the subalpine zone, mainly in forests and shaded habitats. Along with A. napellus, A. lycoctonum is of the most common European species of the Aconitum genus. They are also grown ornamentally in gardens, thriving well in ordinary garden soil. As such, A. lycoctonum can be found in North America, especially in eastern Canada, often in old gardens or as garden escapees.

<i>Aconitum carmichaelii</i> Species of plant


Aconitum carmichaelii is a species of flowering plant of the genus Aconitum, family Ranunculaceae. It is native to East Asia and eastern Russia. It is commonly known as Chinese aconite, Carmichael's monkshood or Chinese wolfsbane. In Mandarin Chinese, it is known as fùzǐ and as wūtóu ; while in Japanese it is named torikabuto.

<i>Aconitum napellus</i> Species of plant

Aconitum napellus, monkshood, aconite, Venus' chariot or wolfsbane, is a species of highly toxic flowering plants in the genus Aconitum of the family Ranunculaceae, native and endemic to western and central Europe. It is an herbaceous perennial plant growing to 1 m tall, with hairless stems and leaves. The leaves are rounded, 5–10 cm (2.0–3.9 in) diameter, palmately divided into five to seven deeply lobed segments. The flowers are dark purple to bluish-purple, narrow oblong helmet-shaped, 1–2 cm (0.39–0.79 in) tall. Plants native to Asia and North America formerly listed as A. napellus are now regarded as separate species. The plant is extremely poisonous in both ingestion and body contact.

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Delphinine is a toxic diterpenoid alkaloid found in plants from the Delphinium (larkspur) and Atragene genera, both in the family Ranunculaceae. Delphinine is the principal alkaloid found in Delphinium staphisagria seeds – at one time, under the name stavesacre, a very well known herbal treatment for body lice. It is related in structure and has similar effects to aconitine, acting as an allosteric modulator of voltage gated sodium channels, and producing low blood pressure, slowed heart rate and abnormal heart rhythms. These effects make it highly poisonous. While it has been used in some alternative medicines, most of the medical community does not recommend using it due to its extreme toxicity.

Lakhvinder Cheema was murdered on 27 January 2009 in Southall, West London, by his former lover, Lakhvir Kaur Singh through the use of poison derived from the Aconitum ferox plant, which contains the highly toxic alkaloid pseudaconitine. Singh became known as "The Curry Killer" due to the food to which the poison was added. The case is of note due to the cruel method of killing and the degree of premeditation, with Singh travelling to India to procure bikh poison, prepared from Aconitum ferox. Singh received a life sentence with a 23-year minimum term.

<span class="mw-page-title-main">Gigactonine</span> Chemical compound

Gigactonine is a naturally occurring diterpene alkaloid first isolated from Aconitum gigas. It occurs widely in the Ranunculaceae plant family. The polycyclic ring system of this chemical compound contains nineteen carbon atoms and one nitrogen atom, which is the same as in aconitine and this is reflected in its preferred IUPAC name.

<i>Aconitum coreanum</i> Species of plant

Aconitum coreanum, known as Korean monkshood, is one of the species of Aconitum. It is one of the crude botanical drugs that has been applied in Chinese medicine during past decades.

<span class="mw-page-title-main">Delsoline</span> Naturally occurring chemical compound

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<i>Aconitum degenii</i> Species of plant

Aconitum degenii is a species of flowering plant in the buttercup family known by the common name branched monkshood .

<i>Aconitum plicatum</i> Species of plant

Aconitum plicatum is a species of flowering plant in the buttercup family known by the common name garden monkshood.

Aconitum soongaricum is a poisonous perennial herbaceous plant species of the genus Aconitum.

<i>Aconitum firmum</i> Species of flowering plant

Aconitum firmum is a species of monkshood that is found in Southern Poland, Slovakia, and Czechia, with a few instances in Ukraine and Romania.

References

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