2-Methoxyethyl-18-methoxycoronaridinate
Identifiers
PubChem CID
ChemSpider
Chemical and physical data
FormulaC24H32N2O4
Molar mass412.530 g·mol−1
3D model (JSmol)
  • COCCOC(=O)C12CC(C4)CN(C2C4CCOC)CCc5c1[nH]c3ccccc35
  • InChI=1S/C24H32N2O4/c1-28-10-8-17-13-16-14-24(23(27)30-12-11-29-2)21-19(7-9-26(15-16)22(17)24)18-5-3-4-6-20(18)25-21/h3-6,16-17,22,25H,7-15H2,1-2H3/t16-,17+,22+,24-/m1/s1 checkY
  • Key:OLFXZBDPKBSIPG-JIQZGXBJSA-N checkY
  (verify)

(−)-2-Methoxyethyl-18-methoxycoronaridinate (ME-18-MC) 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 similar efficacy to the related compound 18-methoxycoronaridine (18-MC) at reducing self-administration of morphine and methamphetamine but with higher potency by weight, showing anti-addictive effects at the equivalent of half the minimum effective dose of 18-MC. Similarly to 18-MC itself, ME-18-MC acts primarily as a selective α3β4 nicotinic acetylcholine antagonist, although it has a slightly stronger effect than 18-MC as an NMDA antagonist, and its effects on opioid receptors are weaker than those of 18-MC at all except the kappa opioid receptor, at which it has slightly higher affinity than 18-MC.[2][3]

See also

References

  1. ^ US 6211360, Glick SD, Kuehne ME, "Ibogamine congeners", issued 3 April 2001, assigned to University of Vermont 
  2. ^ Kuehne ME, He L, Jokiel PA, Pace CJ, Fleck MW, Maisonneuve IM, et al. (June 2003). "Synthesis and biological evaluation of 18-methoxycoronaridine congeners. Potential antiaddiction agents". Journal of Medicinal Chemistry. 46 (13): 2716–30. doi:10.1021/jm020562o. PMID 12801235.
  3. ^ Pace CJ, Glick SD, Maisonneuve IM, He LW, Jokiel PA, Kuehne ME, Fleck MW (May 2004). "Novel iboga alkaloid congeners block nicotinic receptors and reduce drug self-administration". European Journal of Pharmacology. 492 (2–3): 159–67. doi:10.1016/j.ejphar.2004.03.062. PMID 15178360.
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