Aconitine - Structure and Reactivity

Structure and Reactivity

The systematic name of Aconitine is (1α,3α,6α,14α,15α,16β)-8-acetyloxy-20-ethyl-3,13,15-trihydroxy-1,6-16-trimethoxy-4-(methoxymethyl)aconitanyl-14-benzoate. It has the chemical formula C₃₄H₄₇NO₁₁ and a molecular weight of 645.75 g/mol. Aconitine belongs to the family of aconitum alkaloids and are barely soluble in water. On the contrary, organic solvents such as chloroform or diethyl ether are very usable. Aconitine is also soluble in mixtures of alcohol and water, if the concentration of alcohol is high enough. Aconitine is very toxic due to different reactive groups. The nitrogen in one of the six-membered ring structure can easily form salts and ions. This turns the molecule into a structure with high binding affinity for polar and lipophilic structures (such as cell membranes and receptors) and makes it possible for the molecule to pass the blood–brain barrier. The acetoxyl group at the c8 position can readily be replaced by a methoxy group, when heating aconitine in methanol, to produce a 8-deacetyl-8-o-methyl derivatives. If aconitine is heated in its dry state, it undergoes a pyrolysis to form pyroaconitine((1α,3α,6α,14α,16β)-20-Ethyl-3,13-dihydroxy-1,6,16-trimethoxy-4-(methoxymethyl)-15-oxoaconitan-14-yl benzoate) with the chemical formula C₃₂H₄₃NO₉.