Voacangine
| Voacangine | |
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12-Methoxyibogamine-18-carboxylic acid, methyl ester |
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Methyl 17-ethyl-7-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18] nonadeca-2(10),4,6,8-tetraene-1-carboxylate[1] |
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| Identifiers | |
| CAS number | 510-22-5  |
| PubChem | 363270, 261793 (15S,17R)-17-ethyl,-15-nonadeca, 10451681 (1S,15S,18S)-15,18-nonadeca,-1-carboxyl, 21598350 (1R,15S,17R,18R)-17-ethyl,-15,18-nonadeca,-1-carboxyl, 10361692 (1S,15R,17S,18S)-17-ethyl,-15,18-nonadeca,-1-carboxyl, 73255 (1S,15S,17S,18S)-17-ethyl,-15,18-nonadeca,-1-carboxyl |
| ChemSpider | 322451  , 229858 (15S,17R)-17-ethyl,-15-nonadeca , 8627098 (1S,15S,18S)-15,18-nonadeca,-1-carboxyl , 10225658 (1R,15S,17R,18R)-17-ethyl,-15,18-nonadeca,-1-carboxyl , 8537141 (1S,15R,17S,18S)-17-ethyl,-15,18-nonadeca,-1-carboxyl , 66007 (1S,15S,17S,18S)-17-ethyl,-15,18-nonadeca,-1-carboxyl |
| MeSH | Voacangine |
| ChEBI | CHEBI:407575 |
| ChEMBL | CHEMBL182120 |
| Jmol-3D images | Image 1 Image 2 |
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| Properties | |
| Molecular formula | C22H28N2O3 |
| Molar mass | 368.47 g mol−1 |
| Exact mass | 368.209992772 g mol-1 |
| Melting point |
136-137 °C, 409-410 K, 277-279 °F |
| log P | 3.748 |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references |
Voacangine (12-methoxyibogamine-18-carboxylic acid methyl ester) is an alkaloid found predominantly in the rootbark of the Voacanga africana tree, as well as in other plants such as Tabernanthe iboga, Tabernaemontana africana, Trachelospermum jasminoides and Ervatamia yunnanensis.[2][3][4][5] It is an iboga alkaloid which commonly serves as a precursor for the semi-synthesis of ibogaine.[6] It has also been demonstrated in animals to have similar anti-addictive properties to ibogaine itself.[7]
[edit] See also
[edit] References
- ^ "Compound Report Card CHEMBL182120 - Voacangine". ChEMBL. https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/407575.
- ^ Patel, M. B.; Miet, C.; Poisson, J. (1967). "Alkaloids of some African Tabernaemontana". Annales Pharmaceutiques Francaises 25 (5): 379–384. PMID 5611538.
- ^ Fatima, T.; Ijaz, S.; Crank, G.; Wasti, S. (1987). "Indole Alkaloids from Trachelospermum jasminoides". Planta Medica 53 (1): 57–59. doi:10.1055/s-2006-962620. PMID 17268963.
- ^ Liu, G.; Liu, X.; Feng, X. Z. (1988). "Ervayunine: A New Indole Alkaloid from Ervatamia yunnanensis". Planta Medica 54 (6): 519–521. doi:10.1055/s-2006-962535. PMID 3212080.
- ^ Jenks, C. W. (2002). "Extraction Studies of Tabernanthe iboga and Voacanga africana". Natural Product Letters 16 (1): 71–76. doi:10.1080/1057563029001/4881. PMID 11942686.
- ^ US patent 2813873, "Derivatives of the Ibogaine Alkaloids", issued 1957-11-19
- ^ Tsing Hua "Antiaddictive Indole Alkaloids in Ervatamia yunnanensis and their Bioactivity". Academic Journal of Second Military Medical University. January 28, 2006. http://www.shvoong.com/medicine-and-health/1611478-antiaddictive-indole-alkaloids-ervatamia-yunnanensis/ Tsing Hua.
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