18-Methoxycoronaridine

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18-Methoxycoronaridine
18-Methoxycoronaridine.svg
Systematic (IUPAC) name
(–)-18-methoxycoronaridine
Clinical data
Legal status
  • US IND filed 2/9/2014
Routes of
administration
oral
Identifiers
CAS Number 308123-60-6 N
PubChem CID: 10248465
ChemSpider 8423952 YesY
Chemical data
Formula C22H28N2O3
Molecular mass 368.47 g/mol
 NYesY (what is this?)  (verify)

(–)-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, nicotine and sucrose.[1] [2] 18-MC is a α3β4 nicotinic antagonist and, in contrast to ibogaine, has no affinity at the α4β2 subtype nor at NMDA-channels nor at the serotonin transporter,[3] and has significantly reduced affinity for sodium channels and for the σ receptor, but retains modest affinity for μ-opioid receptors where it acts as an antagonist,[4] and κ-opioid receptors.[5] The sites of action in the brain include the medial habenula, interpeduncular nucleus,[6][7][8] dorsolateral tegmentum and basolateral amygdala.[9] It has also been shown to produce anorectic effects in obese rats, most likely due to the same actions on the reward system which underlie its anti-addictive effects against drug addiction.[10]

18-MC is in the early stages of human testing by Savant HWP.[11] In 2002 the research team started trying to raise funds for human trials, but were unable to secure the estimated $5 million needed.[12] In January 2010, Obiter Research, a chemical manufacturer in Champaign, Illinois, signed a patent license with Albany Medical College and the University of Vermont allowing them the right to synthesize and market 18-MC and other congeners. National Institute on Drug Abuse gave a $6.5 million grant in 2012 to California based drug developer company Savant HWP for the human trials.[11]

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.[13][14]

Iboga alkaloids.png

See also

References

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  5. Glick SD, Maisonneuve IM, Hough LB, Kuehne ME, Bandarage UK. (±)-18-Methoxycoronaridine: A Novel Iboga Alkaloid Congener Having Potential Anti-Addictive Efficacy. CNS Drug Reviews 1999;5(1):27-42.
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  11. 11.0 11.1 Albany Med scientist closer to addiction drug success timesunion.com June 27, 2014.
  12. Addiction Treatment Strives for Legitimacy. Journal of the American Medical Association. 2002; 288: 3096-3101.
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Further reading

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