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
	Other names Methyl 12-methoxyibogamine-18-carboxylate
Identifiers
CAS Number	510-22-5
ChEBI	CHEBI:407575
ChEMBL	ChEMBL182120
ChemSpider	8537141
Jmol 3D model	Interactive image
MeSH	Voacangine
PubChem	73255
	InChI 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 Key: MMAYTCMMKJYIAM-PHKAQXKASA-N ;
	SMILES O=C(OC)[C@@]43c2nc1ccc(OC)cc1c2CCN5[C@H]3[C@H](C[C@H](C4)C5)CC ;
Properties
Chemical formula	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).
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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]

References