Ibogamine Explained

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".

Chemistry

Synthesis

Ibogamine can be prepared from one-step demethoxycarbonylation process through coronaridine.^[6]

Pharmacology

Like ibogaine, it has seems to have similar pharmacology. It has effects on KOR,^[7] NMDAR, nAChR^[8] and serotonin sites.^[9] It also inhibits acetylcholinesterase and butyrylcholinesterase.^[10]

See also

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

Notes and References

1. 10.1021/ja01534a036 . Bartlett MF, Dickel DF, Taylor WI . 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 . 1958 .
2. 10.1021/jo00209a020 . Kuehne ME, Reider PJ . A synthesis of ibogamine . The Journal of Organic Chemistry . 50 . 9 . 1464–1467 . 1985 .
3. Rastogi K, Kapil RS, Popli SP . New alkaloids from Tabernaemontana divaricata. . Phytochemistry . January 1980 . 19 . 6 . 1209–1212 . 10.1016/0031-9422(80)83085-8. 1980PChem..19.1209R .
4. Levi MS, Borne RF . A review of chemical agents in the pharmacotherapy of addiction . Current Medicinal Chemistry . 9 . 20 . 1807–1818 . October 2002 . 12369879 . 10.2174/0929867023368980 .
5. Glick SD, Kuehne ME, Raucci J, Wilson TE, Larson D, Keller RW, Carlson JN . 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 . September 1994 . 7820611 . 10.1016/0006-8993(94)90948-2 . 1940631 .
6. Krengel F, Mijangos MV, Reyes-Lezama M, Reyes-Chilpa R . Extraction and Conversion Studies of the Antiaddictive Alkaloids Coronaridine, Ibogamine, Voacangine, and Ibogaine from Two Mexican Tabernaemontana Species (Apocynaceae) . Chemistry & Biodiversity . 16 . 7 . e1900175 . July 2019 . 31095891 . 10.1002/cbdv.201900175 . 157058497 .
7. Deecher DC, Teitler M, Soderlund DM, Bornmann WG, Kuehne ME, Glick SD . Mechanisms of action of ibogaine and harmaline congeners based on radioligand binding studies . Brain Research . 571 . 2 . 242–247 . February 1992 . 1377086 . 10.1016/0006-8993(92)90661-R . 17159661 .
8. Arias HR, Targowska-Duda KM, Feuerbach D, Jozwiak K . Coronaridine congeners inhibit human α3β4 nicotinic acetylcholine receptors by interacting with luminal and non-luminal sites . The International Journal of Biochemistry & Cell Biology . 65 . 81–90 . August 2015 . 26022277 . 10.1016/j.biocel.2015.05.015 . free .
9. Web site: Ethnobotany & ethnopharmacology of Tabernaemontana divaricata. . Free Online Library .
10. Vieira IJ, Medeiros WL, Monnerat CS, Souza JJ, Mathias L, Braz-Filho R, Pinto AC, Sousa PM, Rezende CM, Epifanio R . 6 . Two fast screening methods (GC-MS and TLC-ChEI assay) for rapid evaluation of potential anticholinesterasic indole alkaloids in complex mixtures . Anais da Academia Brasileira de Ciências . 80 . 3 . 419–426 . September 2008 . 18797794 . 10.1590/s0001-37652008000300003 .