{{Short description|Anti-convulsant, anti-addictive CNS stimulant alkaloid}} {{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 458622403 | IUPAC_name = [6''R''-(6α,6aβ,7β,9α)]-7-ethyl-6,6a,7,8,9,10,12,13-octahydro-6,9-methano-5''H''-pyrido[1',2':1,2]azepino[4,5-b]indole | image = Ibogamine.svg | image_class = skin-invert-image | alt = Skeletal formula of ibogamine | image2 = Ibogamine_molecule_ball.png | image_class2 = bg-transparent | alt2 = Ball-and-stick model of the ibogamine molecule | width2 = 230
<!--Clinical data--> | tradename = | pregnancy_category = | legal_status = | routes_of_administration =
<!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =
<!--Identifiers--> | CAS_number_Ref = {{cascite|changed|??}} | CAS_number = 481-87-8 | ATC_prefix = none | ATC_suffix = | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 5853 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C19H24N2/c1-2-13-9-12-10-16-18-15(7-8-21(11-12)19(13)16)14-5-3-4-6-17(14)20-18/h3-6,12-13,16,19-20H,2,7-11H2,1H3/t12-,13+,16+,19+/m1/s1 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = LRLCVRYKAFDXKU-YGOSVGOTSA-N | SMILES = CC[C@H]1C[C@@H]2C[C@@H]3[C@H]1N(C2)CCC4=C3NC5=CC=CC=C45 | PubChem = 100217 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 90568
<!--Chemical data--> | C=19 | H=24 | N=2 }}
'''Ibogamine''' is an anti-convulsant, anti-addictive, CNS stimulant alkaloid found in ''Tabernanthe iboga'' and Crepe Jasmine (''Tabernaemontana divaricata'').<ref>{{cite journal | doi = 10.1021/ja01534a036 | vauthors = Bartlett MF, Dickel DF, Taylor WI | 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 | issue = 1 | pages = 126–136 | year = 1958 }}</ref><ref>{{cite journal | doi = 10.1021/jo00209a020 | vauthors = Kuehne ME, Reider PJ | title = A synthesis of ibogamine | journal = The Journal of Organic Chemistry | volume = 50 | issue = 9 | pages = 1464–1467 | year = 1985 }}</ref><ref>{{cite journal | vauthors = Rastogi K, Kapil RS, Popli SP | title = New alkaloids from Tabernaemontana divaricata. | journal = Phytochemistry | date = January 1980 | volume = 19 | issue = 6 | pages = 1209–1212 | doi = 10.1016/0031-9422(80)83085-8| bibcode = 1980PChem..19.1209R }}</ref> Basic research related to how addiction affects the brain has used this chemical.<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>
== Pharmacology == Like ibogaine, it has seems to have similar pharmacology. It has effects on KOR,<ref name="DeecherTeitler1992">{{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> NMDAR, nAChR<ref name="pmid26022277">{{cite journal | vauthors = Arias HR, Targowska-Duda KM, Feuerbach D, Jozwiak K | title = Coronaridine congeners inhibit human α3β4 nicotinic acetylcholine receptors by interacting with luminal and non-luminal sites | journal = The International Journal of Biochemistry & Cell Biology | volume = 65 | issue = | pages = 81–90 | date = August 2015 | pmid = 26022277 | doi = 10.1016/j.biocel.2015.05.015 | doi-access = free }}</ref> and serotonin sites.<ref>{{Cite web|url=https://www.thefreelibrary.com/Ethnobotany+%26+ethnopharmacology+of+Tabernaemontana+divaricata.-a0181406119|title = Ethnobotany & ethnopharmacology of Tabernaemontana divaricata. | work = Free Online Library }}</ref> It also inhibits acetylcholinesterase and butyrylcholinesterase.<ref name="pmid18797794">{{cite journal | vauthors = Vieira IJ, Medeiros WL, Monnerat CS, Souza JJ, Mathias L, Braz-Filho R, Pinto AC, Sousa PM, Rezende CM, Epifanio R | display-authors = 6 | title = Two fast screening methods (GC-MS and TLC-ChEI assay) for rapid evaluation of potential anticholinesterasic indole alkaloids in complex mixtures | journal = Anais da Academia Brasileira de Ciências | volume = 80 | issue = 3 | pages = 419–426 | date = September 2008 | pmid = 18797794 | doi = 10.1590/s0001-37652008000300003 |url= https://www.scielo.br/pdf/aabc/v80n3/a03v80n3.pdf }}</ref>
Ibogamine persistently reduced the self-administration of cocaine and morphine in rats.<ref name="ref4">{{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> The same study found that ibogamine (40 mg/kg) and coronaridine (40 mg/kg) did not produce "any tremor effects in rats that differ significantly from saline control". While the related alkaloids ibogaine (20–40 mg/kg), harmaline (10–40 mg/kg) and desethylcoronaridine (10–40 mg/kg) were "obviously tremorgenic".<ref name="ref4"></ref>
== Chemistry == === Synthesis === Ibogamine can be prepared from one-step demethoxycarbonylation process through coronaridine.<ref name="pmid31095891">{{cite journal | vauthors = Krengel F, Mijangos MV, Reyes-Lezama M, Reyes-Chilpa R | title = Extraction and Conversion Studies of the Antiaddictive Alkaloids Coronaridine, Ibogamine, Voacangine, and Ibogaine from Two Mexican Tabernaemontana Species (Apocynaceae) | journal = Chemistry & Biodiversity | volume = 16 | issue = 7 | article-number = e1900175 | date = July 2019 | pmid = 31095891 | doi = 10.1002/cbdv.201900175 | s2cid = 157058497 }}</ref>
== See also == * Coronaridine * Ibogaine * Ibogaline * Tabernanthine * Voacangine * Ibogaminalog * Harmaline
== References == {{Reflist}}
{{Dependence treatment}} {{Ionotropic glutamate receptor modulators}} {{Opioid receptor modulators}} {{Tryptamines}} {{Chemical classes of psychoactive drugs}}
Category:Alkaloids found in Iboga Category:Azepinoindoles Category:NMDA receptor antagonists Category:Tryptamine alkaloids