Ibogamine

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

Clinical data
ATC code	none
Identifiers
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
CAS Number	481-87-8 N
PubChem CID	100217
ChemSpider	90568 Y
ChEBI	CHEBI:5853 Y
CompTox Dashboard (EPA)	DTXSID30963997
Chemical and physical data
Formula	C19H24N2
Molar mass	280.415 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC[C@H]1C[C@@H]2C[C@@H]3[C@H]1N(C2)CCC4=C3NC5=CC=CC=C45
InChI 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 Y Key:LRLCVRYKAFDXKU-YGOSVGOTSA-N Y
NY (what is this?)  (verify)

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]

Pharmacology

Like ibogaine, it has seems to have similar pharmacology. It has effects on KOR,^[6] NMDAR, nAChR^[7] and serotonin sites.^[8] It also inhibits acetylcholinesterase and butyrylcholinesterase.^[9]

Chemistry

Synthesis

Ibogamine can be prepared from one-step demethoxycarbonylation process through coronaridine.^[10]

See also

• Coronaridine
• Ibogaine
• Ibogaline
• Tabernanthine
• Voacangine
• Ibogaminalog
• Harmaline