2-Methoxyethyl-18-methoxycoronaridinate

From Wikipedia, the free encyclopedia
2-Methoxyethyl-18-methoxycoronaridinate
ME-18-MC structure.png
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
  

(–)-2-Methoxyethyl-18-methoxycoronaridinate (ME-18-MC) is a second generation synthetic derivative of ibogaine developed by the research team led by the pharmacologist from the Albany Medical College and the chemist 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.
Retrieved from ""