Pseudaconitine

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
CAS Number	127-29-7 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL509646 ;
ChemSpider	390354 ;
PubChem CID	3035296;
UNII	5483BY72RT ;
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/s1 Key: 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/s1 Key: YVPYMQHYESYLIR-CERQHTHQBX;
	SMILES 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
Chemical formula	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). verify (what is ?) Infobox 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.^[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]

References

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

[1] "Monkshood". AACC.org. Retrieved 9 November 2018.

[2] Rahman, A, et al, New Norditerpenoid Alkoids from Aconitum falceroni, 2000

[reference1-3] 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

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[2]

[3]

[4]

History

Toxicity and mechanism

Structure and reactivity

See also

References