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Tabernanthine

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
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
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
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 analkaloid found inTabernanthe 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

[edit]

It iskappa opioidagonist (Ki = 0.15 μM) andNMDA receptor (Ki = 10.5 μM)antagonist.[4][5] Compared to ibogaine, it binds weakly toσ1 andσ2 receptors.[5]

See also

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References

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  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. ^abWiart 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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