VOACANGINE Property

Melting point:

223-224℃ (dec.)

Density 

1.25±0.1 g/cm3 (20 ºC 760 Torr)

storage temp. 

Store at -20°C,protect from light

solubility 

DMF: 16 mg/ml; DMSO: 16 mg/ml; DMSO:PBS(pH 7.2) (1:3): 0.33 mg/ml

form 

A crystalline solid

color 

White to off-white

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H332Harmful if inhaled

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P322Specific measures (see …on this label).

P330Rinse mouth.

P363Wash contaminated clothing before reuse.

P501Dispose of contents/container to..…

VOACANGINE Chemical Properties,Usage,Production

Description

This alkaloid is of widespread occurrence, being found in Stemmadenia species and also is Vocanga africana, v. dregii and V. obtusa. It forms colourless needles when crystallized from MeOH and has [0'10 - 42° (c 1.0, CHCI3). It sublimes under vacuum at 135°CjO.01 mm and is readily soluble in CHC13 or Me2CO, but only sparingly so in EtOH or MeOH. Hydrolysis with KOH followed by acidification with HCl yields Ibogaine (q.v.).

Uses

(-)-Voacangine is a bisindole alkaloid with ether-?a-?go-?go-?related gene channel blocker activity in vitro. hERG channel blocker.

Definition

ChEBI: (-)-voacangine is a monoterpenoid indole alkaloid with formula C22H28N2O3, isolated from several plant species. It has a role as an angiogenesis inhibitor, an antineoplastic agent and a plant metabolite. It is a monoterpenoid indole alkaloid, a tertiary amino compound, a methyl ester, an organic heteropentacyclic compound and an alkaloid ester. It is a conjugate base of a (-)-voacangine(1+).

References

lanot, Goutarel., Compt. rend., 241,986 (1955) Stauffacher, Seebeck., Helv. Chim. Acta, 41,169 (1958) Watts, Collera, Sandoval., Tetrahedron, 2, 173 (1958) Schuler, Verbeck, Warren.,J. Chern. Soc., 4776 (1958) Bartlett, Dickel, Taylor.,J. Amer. Chern. Soc., 80, 126 (1958) Renner, Prins, Stoll., Helv. Chim. Acta, 42,1572 (1959) Budzikiewicz etal., Bull. Soc. Chim. Fr., 1899 (1963)