Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C22H28N2O3 |
Molecular Weight | 368.4693 |
Optical Activity | ( - ) |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12[C@@H](CCOC)C[C@H]3C[N@@]1CCC4=C(NC5=CC=CC=C45)[C@@]2(C3)C(=O)OC
InChI
InChIKey=DTJQBBHYRQYDEG-SVBQBFEESA-N
InChI=1S/C22H28N2O3/c1-26-10-8-15-11-14-12-22(21(25)27-2)19-17(7-9-24(13-14)20(15)22)16-5-3-4-6-18(16)23-19/h3-6,14-15,20,23H,7-13H2,1-2H3/t14-,15+,20+,22-/m1/s1
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. 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, 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, and κ-opioid receptors. The sites of action in the brain include the medial habenula, interpeduncular nucleus, dorsolateral tegmentum and basolateral amygdala. Unlike ibogaine and its principal metabolite noribogaine, 18-MC does not increase expression of glial cell line-derived neurotrophic factor (GDNF) in a dopaminergic–like cell line. 18-Methoxycoronaridine is a potent leishmanicide effect against Leishmania amazonensis, a causative agent of cutaneous and diffuse cutaneous leishmaniasis in the New World.
Approval Year
PubMed
Title | Date | PubMed |
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Time-dependent interactions between iboga agents and cocaine. | 1997 Oct 8 |
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Iboga interactions with psychomotor stimulants: panacea in the paradox? | 2001 Jan |
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Addiction treatment strives for legitimacy. | 2002 Dec 25 |
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Anti-HIV-1 activity of the Iboga alkaloid congener 18-methoxycoronaridine. | 2004 Sep |
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Subtypes of neuronal nicotinic acetylcholine receptors involved in nicotine-induced phosphorylation of extracellular signal-regulated protein kinase in PC12h cells. | 2006 Jan 9 |
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Morphine-induced changes in acetylcholine release in the interpeduncular nucleus and relationship to changes in motor behavior in rats. | 2007 Jul |
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Brain regions mediating alpha3beta4 nicotinic antagonist effects of 18-MC on methamphetamine and sucrose self-administration. | 2008 Dec 3 |
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18-Methoxycoronaridine blocks acquisition but enhances reinstatement of a cocaine place preference. | 2009 Jul 17 |
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Interaction of 18-methoxycoronaridine with nicotinic acetylcholine receptors in different conformational states. | 2010 Jun |
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Noribogaine, but not 18-MC, exhibits similar actions as ibogaine on GDNF expression and ethanol self-administration. | 2010 Oct |
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18-Methoxycoronaridine, a potential anti-obesity agent, does not produce a conditioned taste aversion in rats. | 2010 Sep |
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Anti-addiction drug ibogaine inhibits voltage-gated ionic currents: a study to assess the drug's cardiac ion channel profile. | 2013 Dec 1 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21210086
Rats: Pretreatment with 18-MC (20 mg/kg, i.p.), given prior to the administration of ghrelin (1 ug, lateral ventricle), blocked ghrelin-induced increases in sucrose (5%) intake in a two-bottle open access paradigm. Using in vivo microdialysis, 18-MC (both 20 and 40 mg/kg) prevented ghrelin (2 ug, intraventral tegmental area)-induced increases in extracellular dopamine in the nucleus accumbens.
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16289028
In vitro studies have demonstrated that 18-MC is a potent antagonist of alpha3beta4 nicotinic receptors (IC50=0.75 uM), which are predominantly located in the medial habenula and interpeduncular nuclei.
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15479177
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308123-60-6
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18-Methoxycoronaridine
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DTXSID40437331
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DB15096
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KX8NQX91Z8
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SUBSTANCE RECORD