Tabernanthine

Tabernanthine
Clinical data
ATC code	none;
Identifiers
	IUPAC name (1R,15R,17S,18S)-17-ethyl-6-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4(9),5,7-tetraene;
CAS Number	83-94-3;
PubChem CID	6326116;
ChemSpider	4885254;
UNII	TV52I1S16D;
CompTox Dashboard (EPA)	DTXSID50878514 ;
Chemical and physical data
Formula	C20H26N2O
Molar mass	310.441 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCC1CC2CC3C1N(C2)CCC4=C3NC5=C4C=CC(=C5)OC;
	InChI InChI=1S/C20H26N2O/c1-3-13-8-12-9-17-19-16(6-7-22(11-12)20(13)17)15-5-4-14(23-2)10-18(15)21-19/h4-5,10,12-13,17,20-21H,3,6-9,11H2,1-2H3/t12-,13+,17+,20+/m1/s1; Key:UCIDWKVIQZIKEK-CFDPKNGZSA-N;

Tabernanthine is an alkaloid found in Tabernanthe iboga.^[1]

It has been used in laboratory experiments to study how addiction affects the brain.^[2]

Tabernanthine persistently reduced the self-administration of cocaine and morphine in rats.^[3]

^ Bartlett MF, Dickel DF, Taylor WI (1958). "The Alkaloids of Tabernanthe iboga. Part IV.1 The Structures of Ibogamine, Ibogaine, Tabernanthine and Voacangine". Journal of the American Chemical Society. 80 (1): 126–136. Bibcode:1958JAChS..80..126B. doi:10.1021/ja01534a036.
^ Levi MS, Borne RF (October 2002). "A review of chemical agents in the pharmacotherapy of addiction". Current Medicinal Chemistry. 9 (20): 1807–1818. doi:10.2174/0929867023368980. PMID 12369879.
^ Glick SD, Kuehne ME, Raucci J, Wilson TE, Larson D, Keller RW, Carlson JN (September 1994). "Effects of iboga alkaloids on morphine and cocaine self-administration in rats: relationship to tremorigenic effects and to effects on dopamine release in nucleus accumbens and striatum". Brain Research. 657 (1–2): 14–22. doi:10.1016/0006-8993(94)90948-2. PMID 7820611. S2CID 1940631.