ethanol: 35 mg/mL Aconitine is an alkaloid toxin produced by various plant species belonging to the genus Aconitum (family Ranunculaceae), commonly known by the names wolfsbane and monkshood.

Biologically active isolates from Aconitum and Delphinium plants are classified as norditerpenoid alkaloids,[1] which are further subdivided based on the presence or absence of the C18 carbon.

[6] 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.

[7][8] Aconitine can interact with the voltage-dependent sodium-ion channels, which are proteins in the cell membranes of excitable tissues, such as cardiac and skeletal muscles and neurons.

At high concentration (0.3–3 μM), the sodium-ion channels are constantly activated, transmission of action potentials is suppressed, leading to non-excitable target cells or paralysis.

In particular, despite over one hundred years having elapsed since its isolation, the prototypical member of its family of norditerpenoid alkaloids, aconitine itself, represents a rare example of a well-known natural product that has yet to succumb to efforts towards its total synthesis.

The challenge that aconitine poses to synthetic organic chemists is due to both the intricate interlocking hexacyclic ring system that makes up its core and the elaborate collection of oxygenated functional groups at its periphery.

Heating in methanol with potassium hydroxide causes an aldol condensation to close the sixth and final ring in napelline (14).

There has been research in 2011 in China to investigate in-depth the CYPs involved in aconitine metabolism in human liver microsomes.

The proposed metabolic pathways of aconitine in human liver microsomes and the CYPs involved to it are summarized in the table above.

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.

[22] Consuming as little as 2 milligrams of pure aconitine or 1 gram of the plant itself may cause death by paralyzing respiratory or heart functions.

[23] The toxic effects of aconitine have been tested in a variety of animals, including mammals (dog, cat, guinea pig, mouse, rat and rabbit), frogs and pigeons.

For the analysis of the Aconitum alkaloids in biological specimens such as blood, serum and urine, several GC-MS methods have been described.

Aconitine was the poison used by George Henry Lamson in 1881 to murder his brother-in-law in order to secure an inheritance.

[30][31][32] Rufus T. Bush, American industrialist and yachtsman, died on September 15, 1890, after accidentally taking a fatal dose of aconite.

In 1953 aconitine was used by a Soviet biochemist and poison developer, Grigory Mairanovsky, in experiments with prisoners in the secret NKVD laboratory in Moscow.

The poet Ovid, referring to the proverbial dislike of stepmothers for their step-children, writes: Lurida terribiles miscent aconita novercae.

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 father to protagonist Leopold Bloom used pastilles of the chemical to commit suicide.

Aconitine poisoning plays a key role in the murder mystery Breakdown by Jonathan Kellerman (2016).

In Twin Peaks season 3 part 13, aconitine is suggested as a means to poison the main character.

Hannah McKay (Yvonne Strahovski), a serial killer in the Showtime series Dexter uses aconite on at least three occasions to poison her victims.

In season 2 episode 16 of the series Person Of Interest, aconitine is shown in a syringe stuck to the character Shaw (Sarah Shahi) nearly being injected and causing her death, until she is rescued by Reese (Jim Caviezel).

In a 2017 episode of The Doctor Blake Mysteries, fight manager Gus Jansons (Steve Adams) murdered his boxer, Mickey Ellis (Trey Coward), during a match by applying aconitine he had put in petroleum jelly and applying it to a cut over the boxer’s eye.