18-Methylaminocoronaridine

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18-Methylaminocoronaridine
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Identifiers
PubChem CID: 44325016
ChemSpider 24721797 YesY
Chemical data
Formula C22H29N3O2
Molecular mass 367.483 g/mol
  • c4cccc1c4nc3c1CCN2CC(C5)CC3(C(=O)OC)C2C5CCNC
  • InChI=1S/C22H29N3O2/c1-23-9-7-15-11-14-12-22(21(26)27-2)19-17(8-10-25(13-14)20(15)22)16-5-3-4-6-18(16)24-19/h3-6,14-15,20,23-24H,7-13H2,1-2H3/t14-,15+,20+,22-/m1/s1 YesY
  • Key:YKMOJVPLIUXEIP-SVBQBFEESA-N YesY
  (verify)

(–)-18-Methylaminocoronaridine (18-MAC) is a second generation synthetic derivative of ibogaine developed by the research team led by the pharmacologist Stanley D. Glick from the Albany Medical College and the chemist Martin E. Kuehne from the University of Vermont.[1] In animal studies it has shown around twice the efficacy of the related compound 18-methoxycoronaridine (18-MC) at reducing self-administration of morphine when administered in an equivalent dose, although it is less effective than 18-MC at reducing methamphetamine administration. Similarly to 18-MC itself, 18-MAC acts primarily as a selective α3β4 nicotinic acetylcholine antagonist, and is even more selective than 18-MC with very little activity as an NMDA antagonist and only slight affinity for the delta opioid receptor.[2][3]

See also

References

  1. Stanley D. Glick, Martin E. Kuehne. Ibogamine congeners. US Patent 6211360
  2. Kuehne ME, He L, Jokiel PA, Pace CJ, Fleck MW, Maisonneuve IM, Glick SD, Bidlack JM. Synthesis and biological evaluation of 18-methoxycoronaridine congeners. Potential antiaddiction agents. Journal of Medicinal Chemistry. 2003 June 19;46(13):2716-30. PMID 12801235
  3. Pace CJ, Glick SD, Maisonneuve IM, He LW, Jokiel PA, Kuehne ME, Fleck MW. Novel iboga alkaloid congeners block nicotinic receptors and reduce drug self-administration. European Journal of Pharmacology. 2004 May 25;492(2-3):159-67. PMID 15178360