Isovoacangine

Isovoacangine is a naturally occurring substance related to voacangine. It showed negative chronotropic and negative inotropic activity.[1]

Isovoacangine

Identifiers
IUPAC name methyl 17-ethyl-6-methoxy-3,13-diazapentacyclo[13.3.1.0^2,10.0^4,9.0^13,18]nonadeca-2(10),4(9),5,7-tetraene-1-carboxylate
PubChem CID	494627
ChemSpider	432954
ChEMBL	ChEMBL360427
Chemical and physical data
Formula	C22H28N2O3
Molar mass	368.477 g·mol^−1
3D model (JSmol)	Interactive image
SMILES CCC1CC2CC3(C1N(C2)CCc4c3[nH]c5c4ccc(c5)OC)C(=O)OC
InChI InChI=1S/C22H28N2O3/c1-4-14-9-13-11-22(21(25)27-3)19-17(7-8-24(12-13)20(14)22)16-6-5-15(26-2)10-18(16)23-19/h5-6,10,13-14,20,23H,4,7-9,11-12H2,1-3H3 Key:FPUHKQMDWMVBRI-UHFFFAOYSA-N

Chemistry

Derivatives

3-Hydroxyisovoacangine and 3-(2'-oxopropyl)isovoacangine are derivates of isovoacangine.[2]

Natural occurrence

It occurs naturally in many Tabernaemontana (milkwood) species such as Tabernaemontana pachysiphon and Tabernaemontana_divaricata.[3][4]

See also

• voacangine
• Tabernanthine
• Ibogaine

References

1. Pratchayasakul W, Pongchaidecha A, Chattipakorn N, Chattipakorn S (April 2008). "Ethnobotany & ethnopharmacology of Tabernaemontana divaricata" (PDF). The Indian Journal of Medical Research. 127 (4): 317–35. PMID 18577786. S2CID 1119874.
2. Danieli B, Palmisano G (January 1987). "Alkaloids from Tabernaemontana.". In Brossi A (ed.). The alkaloids: Chemistry and Pharmacology. 27. Academic Press. pp. 1–130 (82). ISBN 978-0-08-086551-5.
3. "Tabernaemontana undulata - Useful Tropical Plants". tropical.theferns.info.
4. Kam TS, Loh KY, Wei C (November 1993). "Conophylline and conophyllidine: new dimeric alkaloids from Tabernaemontana divaricata". Journal of Natural Products. 56 (11): 1865–71. doi:10.1021/np50101a001.