Ibogamine

Ibogamine
Skeletal formula of ibogamine
Ball-and-stick model of the ibogamine molecule
Clinical data
ATC code
  • none
Identifiers
  • [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
CAS Number
PubChem CID
ChemSpider
ChEBI
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H24N2
Molar mass280.415 g·mol−1
3D model (JSmol)
  • CC[C@H]1C[C@@H]2C[C@@H]3[C@H]1N(C2)CCC4=C3NC5=CC=CC=C45
  • InChI=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 checkY
  • Key:LRLCVRYKAFDXKU-YGOSVGOTSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Ibogamine is an anti-convulsant, anti-addictive, CNS stimulant alkaloid found in Tabernanthe iboga and Crepe Jasmine (Tabernaemontana divaricata).[1][2][3] Basic research related to how addiction affects the brain has used this chemical.[4]

Ibogamine persistently reduced the self-administration of cocaine and morphine in rats.[5] 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".[5]

  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. doi:10.1021/ja01534a036.
  2. ^ Kuehne ME, Reider PJ (1985). "A synthesis of ibogamine". The Journal of Organic Chemistry. 50 (9): 1464–1467. doi:10.1021/jo00209a020.
  3. ^ Rastogi K, Kapil RS, Popli SP (January 1980). "New alkaloids from Tabernaemontana divaricata". Phytochemistry. 19 (6): 1209–1212. Bibcode:1980PChem..19.1209R. doi:10.1016/0031-9422(80)83085-8.
  4. ^ 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.
  5. ^ a b 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.