Ibogamine

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Ibogamine
Ibogamine.svg
Ibogamine molecule ball.png
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
Formula C19H24N2
Molar mass 280.415 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 Yes check.svgY
  • Key:LRLCVRYKAFDXKU-YGOSVGOTSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (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]

Contents

Pharmacology

Like ibogaine, it has seems to have similar pharmacology. It has effects on KOR, [5] NMDAR, nAChR [6] and serotonin sites. [7] It also inhibits acetylcholinesterase and butyrylcholinesterase. [8]

Ibogamine persistently reduced the self-administration of cocaine and morphine in rats. [9] 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". [9]

Chemistry

Synthesis

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

See also

References

  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. ↑ 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.
  6. ↑ 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.
  7. ↑ "Ethnobotany & ethnopharmacology of Tabernaemontana divaricata". Free Online Library.
  8. ↑ 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.
  9. 1 2 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.
  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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