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Voacangine

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Title: Voacangine  
Author: World Heritage Encyclopedia
Language: English
Subject: Ibogaine, Voacanga africana, Noribogaine, Solanaceae, Tabernanthine
Collection: Alkaloids Found in Iboga, Carboxylate Esters, Drug Rehabilitation, Indole Alkaloids, Methyl Esters, Phenol Ethers
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Voacangine

Voacangine
Stereo structural formula of voacangine
Names
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
 Y
ChEBI  N
ChEMBL  N
ChemSpider  N
Jmol-3D images Image
MeSH
PubChem
Properties
C22H28N2O3
Molar mass 368.48 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).
 N  (: Y/N?)

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]

See also

References

  1. ^ "Compound Report Card CHEMBL182120 - Voacangine". ChEMBL. 
  2. ^ Patel, M. B.; Miet, C.; Poisson, J. (1967). "Alkaloids of some African Tabernaemontana". Annales Pharmaceutiques Francaises 25 (5): 379–384.  
  3. ^ Fatima, T.; Ijaz, S.; Crank, G.; Wasti, S. (1987). "Indole Alkaloids from Trachelospermum jasminoides". Planta Medica 53 (1): 57–59.  
  4. ^ Liu, G.; Liu, X.; Feng, X. Z. (1988). "Ervayunine: A New Indole Alkaloid from Ervatamia yunnanensis". Planta Medica 54 (6): 519–521.  
  5. ^ Jenks, C. W. (2002). "Extraction Studies of Tabernanthe iboga and Voacanga africana". Natural Product Letters 16 (1): 71–76.  
  6. ^ US patent 2813873, "Derivatives of the Ibogaine Alkaloids", issued 1957-11-19 
  7. ^ and their Bioactivity"Ervatamia yunnanensisTsing Hua "Antiaddictive Indole Alkaloids in . Academic Journal of Second Military Medical University. January 28, 2006. 
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