Voacangine
Basic information
- CAS
510-22-5- Standard SMILES
CC[C@H]1C[C@@H]2CN3CCc4c([nH]c5ccc(OC)cc45)[C@](C(=O)OC)(C2)[C@H]13- InChIKey
MMAYTCMMKJYIAM-RUGRQLENSA-N- Molecular formula
- C22H28N2O3
- Average molar mass
- 368.5 g/mol
- Monoisotopic mass
- 368.20999276
Overview
(-)-voacangine is a monoterpenoid indole alkaloid with formula C22H28N2O3, isolated from several plant species. It has a role as an antineoplastic agent, an angiogenesis inhibitor and a plant metabolite. It is a methyl ester, an organic heteropentacyclic compound, an alkaloid ester, a tertiary amino compound and a monoterpenoid indole alkaloid. It is a conjugate base of a (-)-voacangine(1+).
Names & identifiers
- Preferred name
- Voacangine
- IUPAC
- methyl (1S,15S,17S,18S)-17-ethyl-7-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4(9),5,7-tetraene-1-carboxylate
- English name
- VOACANGINE
- Molecular formula
- C22H28N2O3
- Molecular weight
- 368.47
Names & synonyms
Voacangine(-)-VoacangineCarbomethoxyibogaine510-22-512-Methoxyibogamine-18-carboxylic acid methyl ester9SY76D3YUKCHEBI:141966methyl (1S,15S,17S,18S)-17-ethyl-7-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4(9),5,7-tetraene-1-carboxylateIbogamine-18-carboxylic acid, 12-methoxy-, methyl estermethyl (1S,15S,17S,18S)-17-ethyl-7-methoxy-3,13-diazapentacyclo(13.3.1.02,10.04,9.013,18)nonadeca-2(10),4(9),5,7-tetraene-1-carboxylateRefChem:194597methyl (1S,15R,17S,18S)-17-ethyl-7-methoxy-3,13-diazapentacyclo(13.3.1.02,10.04,9.013,18)nonadeca-2(10),4(9),5,7-tetraene-1-carboxylate
Show more names
methyl 17-ethyl-7-methoxy-3,13-diazapentacyclo(13.3.1.02,10.04,9.013,18)nonadeca-2(10),4(9),5,7-tetraene-1-carboxylateCHEMBL182120methyl (6xi)-12-methoxy-2alpha-ibogamine-18-carboxylatemethyl ethyl(methoxy)[?]carboxylateDTXSID50965276MMAYTCMMKJYIAM-RUGRQLENSA-NMethyl 12-methoxyibogamine-18-carboxylateUNII-9SY76D3YUK
Properties
Computed structural properties
- XLogP
- 3.5
- Topological polar surface area
- 54.6 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 4
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 598
Physicochemical properties
- Melting point
- 223 · 223-224℃ (dec.)
- Boiling point
- 518.39 · 518.390±50.00 °C(Press: 760.00 Torr)(predicted)
- Density
- 1.25 · 1.25±0.1 g/cm3 (20 ºC 760 Torr)
- storage temp.
- -20 °C,protect · Store at -20°C,protect from light
- solubility
- 16 mg/ml; · DMF: 16 mg/ml; DMSO: 16 mg/ml; DMSO:PBS(pH 7.2) (1:3): 0.33 mg/ml
- form
- A crystalline solid
- pka
- 16.344 · 16.344±0.60(predicted)
- color
- White to off-white
- FDA UNII
- 9 SY76D3YUK · 9SY76D3YUK
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H312-H332
- Precautionary statements
- 264 · P264-P270-P301+P312-P330-P501-P261-P271-P304+P340-P312-P280-P302+P352-P312-P322-P363-P501
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H312-H332
- Precautionary statements
- P264-P270-P301+P312-P330-P501-P261-P271-P304+P340-P312-P280-P302+P352-P312-P322-P363-P501
Chemistry & industry
Applications
DescriptionThis 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.
Additional notes
DefinitionChEBI: (-)-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+).
Related reactions
1 records
Compound notes
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