Ibogamine

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 ;
PubChem CID	100217;
ChemSpider	90568 ;
ChEBI	CHEBI:5853 ;
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 ; Key:LRLCVRYKAFDXKU-YGOSVGOTSA-N ;
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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]

^ 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.
^ Kuehne ME, Reider PJ (1985). "A synthesis of ibogamine". The Journal of Organic Chemistry. 50 (9): 1464–1467. doi:10.1021/jo00209a020.
^ 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.
^ 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.
^ ^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.

[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.

[ref4-5] 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.

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