Voacangine

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Voacangine
Stereo structural formula of voacangine
Identifiers
CAS number 510-22-5 YesY
PubChem 73255
ChemSpider 8537141 N
MeSH Voacangine
ChEBI CHEBI:407575 N
ChEMBL CHEMBL182120 N
Jmol-3D images Image 1
Properties
Molecular formula C22H28N2O3
Molar mass 368.47 g mol−1
Melting point 136 to 137 °C (277 to 279 °F; 409 to 410 K)
log P 3.748
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
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]

See also[edit]

References[edit]

  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. PMID 5611538. 
  3. ^ 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. 
  4. ^ 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. 
  5. ^ 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. 
  6. ^ US patent 2813873, "Derivatives of the Ibogaine Alkaloids", issued 1957-11-19 
  7. ^ Tsing Hua "Antiaddictive Indole Alkaloids in Ervatamia yunnanensis and their Bioactivity". Academic Journal of Second Military Medical University. January 28, 2006.