VOACANGINE Chemical Properties

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

VOACANGINE Usage And Synthesis

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)

VOACANGINE(510-22-5)Related Product Information

• 3-(2-methylaminoethyl)-1H-indol-5-ol
• N,N-Dimethyl-5-methoxytryptamine
• 2-TERT-BUTYL-1H-INDOLE
• 3,5-Dimethylpiperidine
• METHYL BETA-(DIMETHYLAMINO)ISOBUTYRATE
• Methyl piperidine-3-carboxylate
• (R)-Methyl nipecotate
• 2-Piperidineethanol
• Bufotenine
• 1-METHYL-1-CYCLOHEXANECARBOXYLIC ACID
• N,N-DIPROPYLTRYPTAMINE
• INDOLE-2-ACETIC ACID
• CHEMBRDG-BB 5569568
• 5-METHOXY-N,N-DIETHYLTRYPTAMINE(5-MEO-DET)
• VOACANGINE
• 2,6-DIMETHYLCYCLOHEXYLAMINE
• 3-AMINO-HEPTANOIC ACID
• 5-Methoxy-N,N-dipropyltryptamine