Ibogamine

Ibogamine
Skeletal formula of ibogamine
Ball-and-stick model of the ibogamine molecule
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
PubChem CID
ChemSpider
ChEBI
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H24N2
Molar mass280.415 g·mol−1
3D model (JSmol)
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 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]

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 acetycholinestearase and butrylcholinestearase[10]

See also

References

  1. ↑ Bartlett, M. F.; Dickel, D. F.; Taylor, W. I. (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, Martin E.; Reider, Paul J. (1985). "A synthesis of ibogamine". The Journal of Organic Chemistry. 50 (9): 1464–1467. doi:10.1021/jo00209a020.
  3. ↑ Ankita Kulshreshtha, Jyoti Saxena. "Alkaloids and Non Alkaloids of Tabernaemontana divaricata" (PDF). Archived from the original (PDF) on 25 June 2020. {{cite journal}}: Cite journal requires |journal= (help)CS1 maint: uses authors parameter (link)
  4. ↑ Levi MS, Borne RF (October 2002). "A review of chemical agents in the pharmacotherapy of addiction". Curr. Med. Chem. 9 (20): 1807–18. doi:10.2174/0929867023368980. PMID 12369879.
  5. 1 2 Glick SD, Kuehne ME, Raucci J, Wilson TE, Larson D, Keller RW Jr, 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 Res. 657 (1–2): 14–22. doi:10.1016/0006-8993(94)90948-2. PMID 7820611. S2CID 1940631.
  6. ↑ 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.
  7. ↑ Deecher, Darlene C.; Teitler, Milton; Soderlund, David M.; Bornmann, William G.; Kuehne, Martin E.; Glick, Stanley D. (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. ISSN 0006-8993. PMID 1377086. S2CID 17159661.
  8. ↑ 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.
  9. ↑ "Ethnobotany & ethnopharmacology of Tabernaemontana divaricata. - Free Online Library".
  10. ↑ "Annals of the Brazilian Academy of Sciences" (PDF).



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