Aconitine - Wikipedia, the free encyclopedia

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Aconitine
From Wikipedia, the free encyclopedia

Aconitine (sometimes known as the Queen of Poisons) is a

highly poisonous alkaloid derived from various aconite
species.

Aconitine

Contents
1 Uses
2 Composition
3 Effects
4 Aconite poisoners
5 References
6 External links

Uses
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]

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

IUPAC name
(1,3,6,14,16)-8-(acetyloxy)-20-ethyl-3,13,15trihydroxy-1,6,16-trimethoxy4-(methoxymethyl)aconitan-14-yl benzoate
Identifiers
CAS
302-27-2
number
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 C34H47 NO11
formula
Molar
645.74 g mol1
mass
Except where noted otherwise, data are given for
materials in their standard state (at 25 C, 100 kPa)
Infobox references

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 1.56 mg aconitine were reported to be lethal in
humans.[4]

Effects
It is quickly absorbed via mucous membranes, but also via skin. Respiratory paralysis, in very high doses also

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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] The anti-dysrhythmic drug
lidocaine, which is clinically used for treating unusual cardiac rhythms, also blocks these sodium channels and
there is a single report of a successful treatment of accidental aconitine poisoning using this drug.[7] Serum or
urine concentrations of the chemical may be measured to confirm diagnosis in hospitalized poisoning victims,
while postmortem blood levels have been reported in at least 5 fatal cases[8]

Aconite poisoners
Aconitine was the poison used by George Henry Lamson in 1881 to murder his brother-in-law in order to secure
an inheritance. Lamson had learnt about aconitine as a medical student from Professor Robert Christison, who
had taught that it was undetectablebut forensic science had improved since Lamson's student days.[9][10][11]
Aconitine was also made famous by its use in Oscar Wilde's 1891 story Lord Arthur Savile's Crime. Aconite
also plays a prominent role in James Joyce's Ulysses, in which the protagonist Leopold Bloom's father used
pastilles of the chemical to commit suicide.
In 2009 Lakhvir Singh of Feltham, west London, used aconitine to poison the food of her ex-lover (who died as
a result of the poisoning) and his current fiance in what is believed to be the first such case since Lamson's use
of the poison. Singh has since received a life sentence for the murder.[12]

References
1. ^ Wang SY, Wang GK (February 2003). "Voltage-gated sodium channels as primary targets of diverse
lipid-soluble neurotoxins". Cellular Signalling 15 (2): 1519. doi:10.1016/S0898-6568(02)00085-2
(http://dx.doi.org/10.1016%2FS0898-6568%2802%2900085-2) . PMID 12464386
(http://www.ncbi.nlm.nih.gov/pubmed/12464386) .
2. ^ Chan TY (April 2009). "Aconite poisoning". Clinical Toxicology (Philadelphia, Pa.) 47 (4): 27985.
doi:10.1080/15563650902904407 (http://dx.doi.org/10.1080%2F15563650902904407) . PMID 19514874
(http://www.ncbi.nlm.nih.gov/pubmed/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 Arzneimittelberdosierungen
(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): 1558. doi:10.1620/tjem.167.155 (http://dx.doi.org
/10.1620%2Ftjem.167.155) . PMID 1475787 (http://www.ncbi.nlm.nih.gov/pubmed/1475787) .
7. ^ Tsukada K, Akizuki S, Matsuoka Y, Irimajiri S (October 1992). "[A case of aconitine poisoning
accompanied by bidirectional ventricular tachycardia treated with lidocaine]". Kokyu to Junkan 40 (10):
10036. PMID 1439251 (http://www.ncbi.nlm.nih.gov/pubmed/1439251) .
8. ^ R. Baselt, Disposition of Toxic Drugs and Chemicals in Man, 8th edition, Biomedical Publications,
Foster City, CA, 2008, pp. 2527.

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9. ^ Macinnis, Peter (2006). It's true!: you eat poison every day. It's true. 18. Allen & Unwin. pp. 8081.
ISBN 1741146267.
10. ^ Macinnis, Peter (2005). Poisons: from hemlock to Botox and the killer bean of Calabar. Arcade
Publishing. pp. 2526. ISBN 1559707615.
11. ^ Parry, Leonard A.; Willard H. Wright (2000). Some Famous Medical Trials. Beard Books. p. 103.
ISBN 1587980312.
12. ^ Poisoning in west London in 2009 (http://news.bbc.co.uk/1/hi/england/london/8492936.stm) - BBC TV
News report 10 February 2010.

External links
Retrieved from "http://en.wikipedia.org/wiki/Aconitine"
Categories: Acetates | Alkaloids | Benzoates | Ion channel toxins | Neurotoxins
This page was last modified on 5 May 2010 at 23:07.
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