18-Methoxycoronaridine

drugbox
IUPAC_name = (-)-18-methoxycoronaridine

---

width = 180
CAS_number = 308123-60-6
ATC_prefix =
ATC_suffix =
PubChem = 10248465
C=22 | H=28 | N=2 | O=3
molecular_weight = 368.47 g/mol
smiles =
melting_point =
melting_high =
bioavailability =
protein_bound =
metabolism =
elimination_half-life =
excretion =
pregnancy_AU =
pregnancy_US =
pregnancy_category =
legal_AU =
legal_CA =
legal_UK =
legal_US =
legal_status =
routes_of_administration =

(-)-18-Methoxycoronaridine (18-MC) is a derivative of ibogaine invented in 1996 by the research team around the pharmacologist Stanley D. Glick from the Albany Medical College and the chemist Martin E. Kuehne from the University of Vermont. In animal studies it has proved to be effective at reducing self-administration of morphine, cocaine, methamphetamine and nicotine. [cite journal | author=S.D. Glick | title=18-Methoxycoronaridine, a non-toxic iboga alkaloid congener:effects on morphine and cocaine self-administration and on mesolimbic dopamine release in rats | journal=Brain Res. | year=1996 | pages=29–35 | volume=719 | issue=1-2 | pmid=8782860 | doi=10.1016/0006-8993(96)00056-X] 18MC is a selective α₃β₄ nicotinic antagonist and, opposed to ibogaine, has no affinity at the α₄β₂ subtype nor at NMDA-channels nor at the serotonin transporter. [cite journal | author=I.M. Maisonneuve | title=Anti-addictive actions of an iboga alkaloid congener: a novel mechanism for a novel treatment | journal=Pharmacol. Biochem. Behav. | year=2003 | pages=607–18 | volume=75 | issue=3 | pmid=12895678 | doi=10.1016/S0091-3057(03)00119-9] 18-MC has not yet been tested in humans. In 2002 the research team started trying to raise funds for human trials, but were unable to secure the estimated $5 million needed. [Addiction Treatment Strives for Legitimacy. "Journal of the American Medical Association". 2002; 288: 3096-3101.] Efforts to raise funds for future trials are still ongoing. [http://www.uvm.edu/~chem/?Page=news.html]

Its CAS number is [308123-60-6] for the free base and [266686-77-5] for the monohydrochloride.

A number of derivatives of 18-MC have also been developed, with several of them being superior to 18-MC itself, the methoxyethyl congener ME-18-MC being more potent than 18-MC but with similar efficacy, and the methylamino analogue 18-MAC being more effective than 18-MC but with around the same potency. These compounds were also found to act as selective α₃β₄ nicotinic acetylcholine antagonists, with little or no effect on NMDA receptors. [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 Jun 19;46(13):2716-30. PMID 12801235] [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]

ee also

*Coronaridine
*Ibogaine
*Noribogaine
*Voacangine

References

Further reading

#