Tabernanthine

Last updated
Tabernanthine
Tabernanthine.svg
Tabernanthine molecule ball.png
Clinical data
ATC code
  • none
Identifiers
  • (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
Formula C20H26N2O
Molar mass 310.441 g·mol−1
3D model (JSmol)
  • CCC1CC2CC3C1N(C2)CCC4=C3NC5=C4C=CC(=C5)OC
  • 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]

Contents

Pharmacology

It is kappa opioid agonist (Ki = 0.15 μM) and NMDA receptor (Ki = 10.5 μM) antagonist. [4] [5] Compared to ibogaine, it binds weakly to σ1 and σ2 receptors. [5]

See also

References

  1. ↑ 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.
  2. ↑ 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.
  3. ↑ 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.
  4. ↑ Deecher DC, Teitler M, Soderlund DM, Bornmann WG, Kuehne ME, Glick SD (February 1992). "Mechanisms of action of ibogaine and harmaline congeners based on radioligand binding studies". Brain Research. 571 (2): 242–247. doi:10.1016/0006-8993(92)90661-r. PMID   1377086. S2CID   17159661.
  5. 1 2 Wiart C (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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