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tabernanthine
Sign in to saveTabernanthine is an alkaloid found in Tabernanthe iboga. It has been used in laboratory experiments to study how addiction affects the brain. Tabernanthine persistently reduced the self-administration of cocaine and morphine in rats.
Chemical data
- Formula
- C20H26N2O
- Molecular weight
- 310.4 g/mol
- IUPAC name
- (1R,15S,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
- SMILES
- CC[C@H]1C[C@H]2C[C@@H]3[C@H]1N(C2)CCC4=C3NC5=C4C=CC(=C5)OC
- InChIKey
- UCIDWKVIQZIKEK-NXWOVTFFSA-N
- XLogP
- 3.9
- Polar surface area
- 28.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 310.204513
Show 5 more facts
- chemical formula
- C₂₀H₂₆N₂O
- canonical SMILES
- CCC1CC2CC3C1N(C2)CCC4=C3NC5=C4C=CC(=C5)OC
- isomeric SMILES
- CC[C@H]1C[C@H]2C[C@@H]3[C@H]1N(C2)CCC4=C3NC5=C4C=CC(=C5)OC
- found in taxon
- Tabernaemontana crassifolia
- Commons category
- Tabernanthine
Sources (1)
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Pharmacology
- See also
- References
Tabernanthine is an alkaloid found in Tabernanthe iboga. It has been used in laboratory experiments to study how addiction affects the brain. Tabernanthine persistently reduced the self-administration of cocaine and morphine in rats.
== Pharmacology == It is kappa opioid agonist (Ki = 0.15 μM) and NMDA receptor (Ki = 10.5 μM) antagonist. Compared to ibogaine, it binds weakly to σ1 and σ2 receptors.
Excerpted from Wikipedia’s “tabernanthine” article, available under the CC BY-SA 4.0 licence.