Tabernanthine

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Tabernanthine
Skeletal formula of tabernanthine
Ball-and-stick model of the tabernanthine molecule
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
E number{{#property:P628}}
CompTox Dashboard (EPA)
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Chemical and physical data
FormulaC20H26N2O
Molar mass310.441 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]

Pharmacology

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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

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References

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