Aconitine

Aconitine

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ImageFile=Aconitine new.pngImageSize=200px
ImageFile1=Aconitine-xtal-3D-sticks-skeletal.pngImageSize1=200px
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Section1= Chembox Identifiers
CASNo=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
Section2= Chembox Properties
Formula=C34H47NO11
MolarMass=645.73708
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MeltingPt=
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Section3= Chembox Hazards
MainHazards=
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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, and is used for creating models of cardiac arrhythmia. Aconitine was previously used as an antipyretic.

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). [aut|Merck & Co. (1989): "The Merck Index. Eleventh Edition": p.117. Rahway, N.J.. ISBN 091191028X ] 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. [aut|Ludewig, R., Regenthal, R. et al. (2007): Akute Vergiftungen und Arzneimittelüberdosierungen (German). ISBN 3-8047-2280-6]

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. [aut|Roth, L., Daunderer, M. & Kormann, K. (1994): "Giftpflanzen - Pflanzengifte". ISBN 3-933203-31-7]

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

References


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  • ACONITINE — L’aconit, renonculacée, se récolte, en France notamment, dans les régions marécageuses et en montagne. Pour extraire l’aconitine, la racine séchée et pulvérisée est épuisée par une solution alcoolique d’acide tartrique; on élimine l’alcool par… …   Encyclopédie Universelle

  • Aconitine — Général Nom IUPAC 20 ethyl 3α,13,15α trihydroxy 1α,6α,16β trimethoxy 4 (methoxymethyl)aconitane 8,14α diyl 8 acetate 14 benzoate No CAS …   Wikipédia en Français

  • Aconitine — A*con i*tine, n. (Chem.) An intensely poisonous alkaloid, extracted from aconite. [1913 Webster] || …   The Collaborative International Dictionary of English

  • aconitine — noun An intensely poisonous alkaloid, extracted from aconite …   Wiktionary

  • aconitine — The exceedingly poisonous active principle (diterpene alkaloid) of Aconitum sp. and Delphinium sp., formerly used as a cardiac sedative and applied externally for neuralgia. * * * acon·i·tine ə kän ə .tēn, tən n a white crystalline intensely… …   Medical dictionary

  • ACONITINE —    a most virulent poison from aconite, and owing to the very small quantity sufficient to cause death, is very difficult of detection when employed in taking away life …   The Nuttall Encyclopaedia

  • aconitine — n. poison extracted from the roots of an aconite (plant having poisonous roots) …   English contemporary dictionary

  • aconitine — acon·i·tine …   English syllables

  • aconitine —   n. poisonous alkaloid obtained from aconite …   Dictionary of difficult words

  • aconitine — n. Pharm. a poisonous alkaloid obtained from the aconite plant …   Useful english dictionary

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