Voacangine
Voacangine (12-methoxyibogamine-18-carboxylic acid methyl ester) is an alkaloid found predominantly in the root bark of the Voacanga africana tree, as well as in other plants such as Tabernanthe iboga, Tabernaemontana africana, Trachelospermum jasminoides, Tabernaemontana_divaricata 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 been demonstrated in animals to have similar anti-addictive properties to ibogaine itself.[7] It also potentiates the effects of barbiturates.[8] Under UV-A and UV-B light its crystals fluoresce blue-green, and it is soluble in ethanol.
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| Names | |
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| IUPAC name
12-Methoxyibogamine-18-carboxylic acid, methyl ester | |
| Systematic IUPAC name
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] | |
| Other names
Methyl 12-methoxyibogamine-18-carboxylate | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.214.137  |
| MeSH | Voacangine |
PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| C22H28N2O3 | |
| Molar mass | 368.477 g·mol−1 |
| Melting point | 136 to 137 °C (277 to 279 °F; 409 to 410 K) |
| log P | 3.748 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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| Infobox references | |
Side Effect
High doses of voacangine produce convulsions and asphyxia.[10]
References
- "Compound Report Card CHEMBL182120 - Voacangine". ChEMBL.
- Patel, M. B.; Miet, C.; Poisson, J. (1967). "Alkaloids of some African Tabernaemontana". Annales Pharmaceutiques Françaises. 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. S2CID 23390825.
- US patent 2813873, "Derivatives of the Ibogaine Alkaloids", issued 1957-11-19
- Tsing Hua (January 28, 2006). "Antiaddictive Indole Alkaloids in Ervatamia yunnanensis and their Bioactivity". Academic Journal of Second Military Medical University.
- http://medind.nic.in/iby/t08/i4/ibyt08i4p317.pdf
- "Annals of the Brazilian Academy of Sciences" (PDF).
- https://www.erowid.org/plants/voacanga_africana/voacanga_africana_info1.shtml
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