:Ibogamine

{{Short description|Anti-convulsant, anti-addictive CNS stimulant alkaloid}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 458622403

| IUPAC_name = [6R-(6α,6aβ,7β,9α)]-7-ethyl-6,6a,7,8,9,10,12,13-octahydro-6,9-methano-5H-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

| alt2 = Ball-and-stick model of the ibogamine molecule

| width2 = 230

| tradename =

| pregnancy_category =

| legal_status =

| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| 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

| 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).{{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 }}{{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 }}{{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 }} Basic research related to how addiction affects the brain has used this chemical.{{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 }}

Ibogamine persistently reduced the self-administration of cocaine and morphine in rats.{{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 }} 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".