8-ACETYL LUDACONITINE Chemical Properties

Melting point:

214°

alpha 

D20 +17° (alc)

Boiling point:

697.88°C (rough estimate)

Density 

1.2083 (rough estimate)

refractive index 

1.6630 (estimate)

pka

12?+-.0.70(Predicted)

8-ACETYL LUDACONITINE Usage And Synthesis

Description

An aconitine alkaloid obtained from A coniturn chasrnanthurn Stapf. by Dunstan and Andrews, the base crystallizes from EtOH as hexagonal prisms or rosettes of fine needles. It has [α]²⁰_Do + IS.3° (EtOH) and gives a series of crystalline salts, e.g. the hydrobromide as hexagonal prisms from H20, m.p. lS3-7°C; [edo - 17.3° or as crystals from EtOH or Et 20, m.p. 217 -SoC and the aurichloride, yellow needles, m.p. 147 -152°C with sintering at 142°C. Indaconitine resembles Aconitine (q. v.) in giving a crystalline precipitate with KMn04 but in this case the crystals are markedly smaller. Four methoxyl groups are present and when the SUlphate is heated in aqueous solution in a sealed tube it furnishes acetic acid and benzoylpseudaconine (Indbenzaconine), as a colourless glass, m.p. 130-3°C; [α]_D + 33.6° (EtOH), also giving crystalline salts: hydrochloride, m.p. 242-4°C; [α]_D - S.Oo (H 20); hydrobromide as the dihydrate, m.p. 247°C (dry) and the aurichloride, rosettes of orange needles, m.p. 180-2°C.
Alkaline hydrolysis gives acetic and benzoic acids and pseudaconine, C2sH4108N. On pyrolysis, the alkaloid loses one mole of acetic acid with the formation of a-pyroindaconitine which is amorphous, m.p. 130-2°C; [α]_D + 91.9° (EtOH), giving a crystalline hydro bromide, m.p. 194-SoC. When inda_x0002_conitine hydrochloride is subjected to the same treatment it yields the isomeric ~-pyroindaconitine, also amorphous, but furnishing a crystalline hydrobromide, m.p. 24S-250°C; [α]_D + 27.6°.

Chemical Properties

White crystalline, amorphous, or syrupy sub stance; salts are optically active; melts at214°C (417.2°F); insoluble in water, solublein alcohol, ether, and chloroform.

Uses

8-Acetyl ludaconitine occurs in the tubers of Indianaconite (bish or Aconitum ferox), found inIndia and Nepal. It is used in arrow poisoningfor hunting. Clinically, it is used in treatingrheumatism.

Health Hazard

Feraconitine is a highly toxic alkaloid. Theacute toxic effects are similar to those ofaconitine. The symptoms from ingestionare drowsiness, nervous disorders, weakness,.

References

Dunstan, Andrews, J. Chern. Soc., 87, 1620 (1905) See also: Bauer, Radjhan., Pharrn. Zent., 72,145 (1931)