Voacangine

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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:141966 ;
ChEMBL	ChEMBL182120 ;
ChemSpider	8537141 ;
ECHA InfoCard	100.214.137
MeSH	Voacangine
PubChem CID	73255;
UNII	9SY76D3YUK ;
CompTox Dashboard (EPA)	DTXSID50965276 ;
	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@@]43c2[nH]c1ccc(OC)cc1c2CCN5[C@H]3[C@H](C[C@H](C4)C5)CC;
Properties
Chemical formula	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). verify (what is ?) Infobox references

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.

^ "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. Bibcode:1987PlMed..53...57F. doi:10.1055/s-2006-962620. PMID 17268963. S2CID 910492.
^ Liu, G.; Liu, X.; Feng, X. Z. (1988). "Ervayunine: A New Indole Alkaloid from Ervatamia yunnanensis". Planta Medica. 54 (6): 519–521. Bibcode:1988PlMed..54..519G. doi:10.1055/s-2006-962535. PMID 3212080. S2CID 84629414.
^ 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. Archived from the original on February 13, 2012. Retrieved August 9, 2008.
^ "Unknown" (PDF).

[1] "Compound Report Card CHEMBL182120 - Voacangine". ChEMBL.

[2] Patel, M. B.; Miet, C.; Poisson, J. (1967). "Alkaloids of some African Tabernaemontana". Annales Pharmaceutiques Françaises. 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. Bibcode:1987PlMed..53...57F. doi:10.1055/s-2006-962620. PMID 17268963. S2CID 910492.

[4] Liu, G.; Liu, X.; Feng, X. Z. (1988). "Ervayunine: A New Indole Alkaloid from Ervatamia yunnanensis". Planta Medica. 54 (6): 519–521. Bibcode:1988PlMed..54..519G. doi:10.1055/s-2006-962535. PMID 3212080. S2CID 84629414.

[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. S2CID 23390825.

[6] US patent 2813873, "Derivatives of the Ibogaine Alkaloids", issued 1957-11-19

[7] Tsing Hua (January 28, 2006). "Antiaddictive Indole Alkaloids in Ervatamia yunnanensis and their Bioactivity". Academic Journal of Second Military Medical University. Archived from the original on February 13, 2012. Retrieved August 9, 2008.

[8] "Unknown" (PDF).

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