Tabernanthine

{{Short description|Chemical compound}} {{Drugbox | IUPAC_name = (1''R'',15''R'',17''S'',18''S'')-17-Ethyl-6-methoxy-3,13-diazapentacyclo[13.3.1.0^2,10.0^4,9.0^13,18]nonadeca-2(10),4(9),5,7-tetraene | image = Tabernanthine.svg | image_class = skin-invert-image | alt = Skeletal formula of tabernanthine | width = 240 | image2 = Tabernanthine molecule ball.png | image_class2 = bg-transparent | alt2 = Ball-and-stick model of the tabernanthine molecule

<!--Clinical data--> | tradename = | pregnancy_category = | legal_status = | routes_of_administration =

<!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =

<!--Identifiers--> | CAS_number = 83-94-3 | ATC_prefix = none | ATC_suffix = | PubChem = 6326116 | ChemSpiderID = 4885254 | UNII = TV52I1S16D

<!--Chemical data--> | C=20 | H=26 | N=2 | O=1 | smiles = CCC1CC2CC3C1N(C2)CCC4=C3NC5=C4C=CC(=C5)OC | StdInChI = 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 | StdInChIKey = UCIDWKVIQZIKEK-CFDPKNGZSA-N }}

'''Tabernanthine''' is an alkaloid found in ''Tabernanthe iboga''.<ref name="urlThe Alkaloids of Tabernanthe iboga. Part IV.1 The Structures of Ibogamine, Ibogaine, Tabernanthine and Voacangine - Journal of the American Chemical Society (ACS Publications)">{{cite journal | title = The Alkaloids of Tabernanthe iboga. Part IV.1 The Structures of Ibogamine, Ibogaine, Tabernanthine and Voacangine | journal = Journal of the American Chemical Society| volume = 80| pages = 126–136| doi = 10.1021/ja01534a036 |year = 1958| vauthors = Bartlett MF, Dickel DF, Taylor WI | issue = 1| bibcode = 1958JAChS..80..126B}}</ref> It has been used in laboratory experiments to study how addiction affects the brain.<ref>{{cite journal | vauthors = Levi MS, Borne RF | title = A review of chemical agents in the pharmacotherapy of addiction | journal = Current Medicinal Chemistry | volume = 9 | issue = 20 | pages = 1807–1818 | date = October 2002 | pmid = 12369879 | doi = 10.2174/0929867023368980 }}</ref> Tabernanthine persistently reduced the self-administration of cocaine and morphine in rats.<ref>{{cite journal | vauthors = Glick SD, Kuehne ME, Raucci J, Wilson TE, Larson D, Keller RW, Carlson JN | title = 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 | journal = Brain Research | volume = 657 | issue = 1–2 | pages = 14–22 | date = September 1994 | pmid = 7820611 | doi = 10.1016/0006-8993(94)90948-2 | s2cid = 1940631 }}</ref>

== Pharmacology == It is kappa opioid agonist (K_i = 0.15&nbsp;μM) and NMDA receptor (K_i = 10.5&nbsp;μM) antagonist.<ref name="pmid1377086">{{cite journal | vauthors = Deecher DC, Teitler M, Soderlund DM, Bornmann WG, Kuehne ME, Glick SD | title = Mechanisms of action of ibogaine and harmaline congeners based on radioligand binding studies | journal = Brain Research | volume = 571 | issue = 2 | pages = 242–247 | date = February 1992 | pmid = 1377086 | doi = 10.1016/0006-8993(92)90661-r | s2cid = 17159661 }}</ref><ref name="Wiart2013">{{cite book| vauthors = Wiart C |title=Lead Compounds from Medicinal Plants for the Treatment of Neurodegenerative Diseases|url=https://books.google.com/books?id=o3opAgAAQBAJ&pg=PA67|date=16 December 2013|publisher=Academic Press|isbn=978-0-12-398383-1|pages=67–69, 73}}</ref> Compared to ibogaine, it binds weakly to σ₁ and σ₂ receptors.<ref name="Wiart2013" />

== See also == * Coronaridine * Ibogamine * Voacangine * Tabernaemontanine * Tabernanthalog

== References == {{Reflist}}

{{Dependence treatment}} {{Ionotropic glutamate receptor modulators}} {{Opioid receptor modulators}} {{Tryptamines}}

Category:Alkaloids found in Iboga Category:Azepines Category:Azepinoindoles Category:NMDA receptor antagonists Category:Psychoplastogens Category:Quinuclidine alkaloids Category:Tryptamine alkaloids

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