Aconitine

Aconitine
IUPAC name	(1α,3α,6α,14α,16β)-8-(acetyloxy)-20-ethyl-3,13,15-trihydroxy-1,6,16-trimethoxy-4-(methoxymethyl)aconitan-14-yl benzoate
Identifiers
CAS number	302-27-2
PubChem	245005
SMILES	COC[C@]12CN(C)[C@@H]3[C@H]4[C@H](OC)C1 [C@@]3([C@H](C[C@H]2O)OC)[C@@H]5C[C@]6 (O)[C@@H](OC)[C@H](O)[C@@]4(OC(C)=O) [C@H]5C6OC(=O)c7ccccc7
Properties
Molecular formula	C34H47NO11
Molar mass	645.74 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Aconitine is a highly poisonous alkaloid derived from various aconite species. It is a neurotoxin that opens TTX-sensitive Na⁺ channels in the heart and other tissues,^[1] and is used for creating models of cardiac arrhythmia. Aconitine was previously used as an antipyretic and analgesic, and still has some limited application in herbal medicine although the narrow therapeutic index makes calculating appropriate dosage difficult.^[2]

Aconitine has the chemical formula C₃₄H₄₇NO₁₁, and is soluble in chloroform or benzene, slightly in alcohol or ether, and only very slightly in water.

The Merck Index gives LD₅₀s for mice: 0.166 mg/kg (intravenously); 0.328 mg/kg intraperitoneally (injected into the body cavity); approx. 1 mg/kg orally (ingested).^[3] In rats, the oral LD₅₀ is given as 5.97 mg/kg. Oral doses as low as 1.5 – 6 mg aconitine were reported to be lethal in humans.^[4]

It is quickly absorbed via mucous membranes, but also via skin. Respiratory paralysis, in very high doses also cardiac arrest, leads to death. A few minutes after ingestion paresthesia starts, which includes tingling in the oral region. This extends to the whole body, starting from the extremities. Anesthesia, sweating and cooling of the body, nausea and vomiting and other similar symptoms follow. Sometimes there is strong pain, accompanied by cramps, or diarrhea. There is no antidote, so only the symptoms can be treated,^[5] traditionally with compounds such as atropine, strychnine or barakol, although it is unclear whether any of these are effective. Some other toxins such as tetrodotoxin which bind to the same target site but have opposite effects, can reduce the effects of aconitine, but are so toxic themselves that death may result regardless.^[6]

Aconitine was probably made most famous by its use in Oscar Wilde's 1891 story Lord Arthur Savile's Crime.

References

1. ^ Wang SY, Wang GK (February 2003). "Voltage-gated sodium channels as primary targets of diverse lipid-soluble neurotoxins". Cellular Signalling 15 (2): 151–9. PMID 12464386. 
2. ^ Chan TY (April 2009). "Aconite poisoning". Clinical Toxicology (Philadelphia, Pa.) 47 (4): 279–85. doi:10.1080/15563650902904407. PMID 19514874. 
3. ^ Merck & Co. (1989): The Merck Index. Eleventh Edition: p.117. Rahway, N.J.. ISBN 091191028X
4. ^ Ludewig, R., Regenthal, R. et al. (2007): Akute Vergiftungen und Arzneimittelüberdosierungen (German). ISBN 3-8047-2280-6
5. ^ Roth, L., Daunderer, M. & Kormann, K. (1994): Giftpflanzen - Pflanzengifte. ISBN 3-933203-31-7
6. ^ Ohno Y, Chiba S, Uchigasaki S, Uchima E, Nagamori H, Mizugaki M, Ohyama Y, Kimura K, Suzuki Y (June 1992). "The influence of tetrodotoxin on the toxic effects of aconitine in vivo". The Tohoku Journal of Experimental Medicine 167 (2): 155–8. PMID 1475787. 

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