Tabernanthine

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

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
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H26N2O
Molar mass310.441 g·mol−1
3D model (JSmol)
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

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]

Pharmacology

It is NMDA receptor (Ki = 10.5 μM) antagonist.[4] Compared to ibogaine, it binds weakly to σ1 and σ2 receptor.[4]

See also

References
  1. Bartlett, M. F.; Dickel, D. F.; Taylor, W. I. (1958). "The Alkaloids of Tabernanthe iboga. Part IV.1 The Structures of Ibogamine, Ibogaine, Tabernanthine and Voacangine". Journal of the American Chemical Society. 80: 126–136. doi:10.1021/ja01534a036.
  2. Levi MS, Borne RF (October 2002). "A review of chemical agents in the pharmacotherapy of addiction". Curr. Med. Chem. 9 (20): 1807–18. doi:10.2174/0929867023368980. PMID 12369879.
  3. Glick SD, Kuehne ME, Raucci J, Wilson TE, Larson D, Keller RW Jr, 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 Res. 657 (1–2): 14–22. doi:10.1016/0006-8993(94)90948-2. PMID 7820611.
  4. Christophe Wiart (16 December 2013). Lead Compounds from Medicinal Plants for the Treatment of Neurodegenerative Diseases. Academic Press. pp. 67–69, 73. ISBN 978-0-12-398383-1.


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