13-04954. Indaconitine [Archived]

Nomenclature

CAS number: 4491-19-4
16-Ethyl-1,6,19-trimethoxy-4-(methoxymethyl)aconitane-3,8,10,11-tetrol 8-acetate 10-benzoate; acetylbenzoylpseudaconine.
C34H47NO10; mol wt 629.74.
C 64.85%, H 7.52%, N 2.22%, O 25.41%.

Description and references

From root of Aconitum chasmanthum Stapf. Ranunculaceae: Dunstan, Andrews, J. Chem. Soc. 87, 1620 (1905). Structure: Gilman, Marion, Can. J. Chem. 42, 2700 (1964).

Chemical structure

Properties

Needles from ether, mp 202-203°. [α]D21 +18.28° (c = 2.18 in alc). Indaconitine and its salts are highly toxic: Cash, Dunstan, Proc. Roy. Soc. (London) B176, 468 (1905). Sol in acetone, chloroform, alcohol, ether; practically insol in water, petr ether.

Derivative

Hydrobromide.

Properties

Prisms from water, mp 183-187°; mp 217-218° from alcohol + ether. [α]D 17.27° (c = 2.991).

Derivative

Hydrochloride trihydrate.

Properties

Needles from alcohol + ether. Anhydr salt mp 166-171°. Very hygroscopic. [α]D20 15.83° (c = 1.921).

Status

This monograph has been retired and is no longer subject to revision or update.