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
COCC[C@H]1C[C@H]2C[N@@]3CCC4=C(NC5=C4C=CC=C5)[C@](C2)([C@H]13)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
| Molecular Formula | C22H28N2O3 |
| Molecular Weight | 368.4693 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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 |
|---|---|---|
| Anti-addiction drug ibogaine inhibits voltage-gated ionic currents: a study to assess the drug's cardiac ion channel profile. | 2013-12-01 |
|
| Noribogaine, but not 18-MC, exhibits similar actions as ibogaine on GDNF expression and ethanol self-administration. | 2010-10 |
|
| 18-Methoxycoronaridine, a potential anti-obesity agent, does not produce a conditioned taste aversion in rats. | 2010-09 |
|
| Interaction of 18-methoxycoronaridine with nicotinic acetylcholine receptors in different conformational states. | 2010-06 |
|
| 18-Methoxycoronaridine blocks acquisition but enhances reinstatement of a cocaine place preference. | 2009-07-17 |
|
| Brain regions mediating alpha3beta4 nicotinic antagonist effects of 18-MC on methamphetamine and sucrose self-administration. | 2008-12-03 |
|
| 18-methoxycoronaridine: a potential new treatment for obesity in rats? | 2008-12 |
|
| Morphine-induced changes in acetylcholine release in the interpeduncular nucleus and relationship to changes in motor behavior in rats. | 2007-07 |
|
| 18-MC acts in the medial habenula and interpeduncular nucleus to attenuate dopamine sensitization to morphine in the nucleus accumbens. | 2007-07 |
|
| 18-Methoxycoronaridine acts in the medial habenula and/or interpeduncular nucleus to decrease morphine self-administration in rats. | 2006-05-10 |
|
| Complementary medicines in psychiatry: review of effectiveness and safety. | 2006-02 |
|
| Subtypes of neuronal nicotinic acetylcholine receptors involved in nicotine-induced phosphorylation of extracellular signal-regulated protein kinase in PC12h cells. | 2006-01-09 |
|
| Attenuation of morphine withdrawal signs by intracerebral administration of 18-methoxycoronaridine. | 2005-11-21 |
|
| Addiction research. Ibogaine therapy: a 'vast, uncontrolled experiment'. | 2005-04-15 |
|
| Anti-HIV-1 activity of the Iboga alkaloid congener 18-methoxycoronaridine. | 2004-09 |
|
| Novel iboga alkaloid congeners block nicotinic receptors and reduce drug self-administration. | 2004-05-25 |
|
| Synthesis and biological evaluation of 18-methoxycoronaridine congeners. Potential antiaddiction agents. | 2003-06-19 |
|
| Anti-addictive actions of an iboga alkaloid congener: a novel mechanism for a novel treatment. | 2003-06 |
|
| Addiction treatment strives for legitimacy. | 2002-12-25 |
|
| Modulation of nicotine self-administration in rats by combination therapy with agents blocking alpha 3 beta 4 nicotinic receptors. | 2002-07-19 |
|
| Metabolism of 18-methoxycoronaridine, an ibogaine analog, to 18-hydroxycoronaridine by genetically variable CYP2C19. | 2002-06 |
|
| Antagonism of alpha 3 beta 4 nicotinic receptors as a strategy to reduce opioid and stimulant self-administration. | 2002-03-01 |
|
| Iboga compounds reverse the behavioural disinhibiting and corticosterone effects of acute methamphetamine: Implications for their antiaddictive properties. | 2001-08-18 |
|
| Iboga interactions with psychomotor stimulants: panacea in the paradox? | 2001-01 |
|
| Drug discrimination studies with ibogaine. | 2001 |
|
| Mechanisms of action of ibogaine: relevance to putative therapeutic effects and development of a safer iboga alkaloid congener. | 2001 |
|
| Interactions between 18-methoxycoronaridine (18-MC) and cocaine: dissociation of behavioural and neurochemical sensitization. | 2000-07-21 |
|
| 18-Methoxycoronaridine differentially alters the sensitized behavioral and dopaminergic responses to repeated cocaine and morphine administration. Implications for sensitization in the mediation of drug addiction. | 2000 |
|
| Time-dependent interactions between iboga agents and cocaine. | 1997-10-08 |
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.
| Substance Class |
Chemical
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| Record UNII |
KX8NQX91Z8
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| Record Status |
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18-Methoxycoronaridine
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