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
JSmol)
SMILES
  • 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

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 receptor.[5]

See also

References

  1. doi:10.1021/ja01534a036
    .
  2. PMID 12369879
    .
  3. S2CID 1940631
    .
  4. S2CID 17159661
    .
  5. ^
    ISBN 978-0-12-398383-1
    .
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