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Ibogamine - Wikipedia Jump to content

Ibogamine

From Wikipedia, the free encyclopedia
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]

Pharmacology

[edit]

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

[edit]

Synthesis

[edit]

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

See also

[edit]

References

[edit]
  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.
  6. ^ Deecher DC, Teitler M, Soderlund DM, Bornmann WG, Kuehne ME, Glick SD (February 1992). "Mechanisms of action of ibogaine and harmaline congeners based on radioligand binding studies". Brain Research. 571 (2): 242–247. doi:10.1016/0006-8993(92)90661-R. PMID 1377086. S2CID 17159661.
  7. ^ Arias HR, Targowska-Duda KM, Feuerbach D, Jozwiak K (August 2015). "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. doi:10.1016/j.biocel.2015.05.015. PMID 26022277.
  8. ^ "Ethnobotany & ethnopharmacology of Tabernaemontana divaricata". Free Online Library.
  9. ^ Vieira IJ, Medeiros WL, Monnerat CS, Souza JJ, Mathias L, Braz-Filho R, et al. (September 2008). "Two fast screening methods (GC-MS and TLC-ChEI assay) for rapid evaluation of potential anticholinesterasic indole alkaloids in complex mixtures" (PDF). Anais da Academia Brasileira de Ciências. 80 (3): 419–426. doi:10.1590/s0001-37652008000300003. PMID 18797794.
  10. ^ Krengel F, Mijangos MV, Reyes-Lezama M, Reyes-Chilpa R (July 2019). "Extraction and Conversion Studies of the Antiaddictive Alkaloids Coronaridine, Ibogamine, Voacangine, and Ibogaine from Two Mexican Tabernaemontana Species (Apocynaceae)". Chemistry & Biodiversity. 16 (7) e1900175. doi:10.1002/cbdv.201900175. PMID 31095891. S2CID 157058497.
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