Voacangine

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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
510-22-5 YesY
ChEBI CHEBI:407575 N
ChEMBL ChEMBL182120 N
ChemSpider 8537141 N
Jmol 3D model Interactive image
MeSH Voacangine
PubChem 73255
  • InChI=1S/C22H28N2O3/c1-4-14-9-13-11-22(21(25)27-3)19-16(7-8-24(12-13)20(14)22)17-10-15(26-2)5-6-18(17)23-19/h5-6,10,13-14,20,23H,4,7-9,11-12H2,1-3H3/t13-,14+,20+,22-/m1/s1 N
    Key: MMAYTCMMKJYIAM-PHKAQXKASA-N N
  • O=C(OC)[C@@]43c2nc1ccc(OC)cc1c2CCN5[C@H]3[C@H](C[C@H](C4)C5)CC
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 verify (what is YesYN ?)
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

References

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  6. ↑ US patent 2813873, "Derivatives of the Ibogaine Alkaloids", issued 1957-11-19 
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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