Aconitine

Aconitine

Names
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
Other names Acetylbenzoylaconine
Identifiers
CAS Number	302-27-2 Y
3D model (Jmol)	Interactive image Interactive image
ChEBI	CHEBI:2430 Y
ChemSpider	214292 Y
ECHA InfoCard	100.005.566
IUPHAR/BPS	2617
PubChem CID	245005
UNII	X8YN71D5WC Y
InChI InChI=1S/C34H47NO11/c1-7-35-15-31(16-41-3)20(37)13-21(42-4)33-19-14-32(40)28(45-30(39)18-11-9-8-10-12-18)22(19)34(46-17(2)36,27(38)29(32)44-6)23(26(33)35)24(43-5)25(31)33/h8-12,19-29,37-38,40H,7,13-16H2,1-6H3/t19-,20-,21+,22-,23+,24+,25-,26?,27+,28-,29+,31+,32-,33+,34-/m1/s1 Y Key: XFSBVAOIAHNAPC-XTHSEXKGSA-N Y InChI=1/C34H47NO11/c1-7-35-15-31(16-41-3)20(37)13-21(42-4)33-19-14-32(40)28(45-30(39)18-11-9-8-10-12-18)22(19)34(46-17(2)36,27(38)29(32)44-6)23(26(33)35)24(43-5)25(31)33/h8-12,19-29,37-38,40H,7,13-16H2,1-6H3/t19-,20-,21+,22-,23+,24+,25-,26?,27+,28-,29+,31+,32-,33+,34-/m1/s1 Key: XFSBVAOIAHNAPC-XTHSEXKGBF
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 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@@H](O)[C@@H]3OC)[C@H]45)(COC)[C@H](O)C[C@@H]6OC)c7ccccc7
Properties
Chemical formula	C34H47NO11
Molar mass	645.73708
Appearance	solid
Melting point	203 to 204 °C (397 to 399 °F; 476 to 477 K)
Solubility in water	H2O: 0.3 mg/mL ethanol: 35 mg/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

ethanol: 35 mg/mL

Aconitine is a toxin produced by the Aconitum plant, also known as devil’s helmet or monkshood. Monkshood is notorious for its toxic properties. In China, aconitine is also used in small doses as an analgesic.

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.

Aconitine belongs to the family of aconitum alkaloids and is barely soluble in water, but very soluble in organic solvents such as chloroform or diethyl ether. Aconitine is also soluble in mixtures of alcohol and water if the concentration of alcohol is high enough. Aconitine is very toxic due to several 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, by 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.

Aconitine is synthesized by the monkshood plant via the terpenoid biosynthesis pathway (MEP chloroplast pathway).