| Identification | Back Directory | [Name]
VOACANGINE | [CAS]
510-22-5 | [Synonyms]
VOACANGINE
(-)-Voacangine
Carbomethoxyibogaine
12-Methoxyibogamine-18-carboxylic acid methyl ester
Ibogamine-18-carboxylic acid, 12-methoxy-, methyl ester | [Molecular Formula]
C22H28N2O3 | [MDL Number]
MFCD00077210 | [MOL File]
510-22-5.mol | [Molecular Weight]
368.47 |
| Chemical Properties | Back Directory | [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 Information | Back Directory | [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+). | [in vivo]
Voacangine significantly suppresses in vitro angiogenesis, such as VEGF-induced tube formation and chemoinvasion[2]. | [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) |
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