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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H28N2O3
Molecular Weight 368.4702
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 18-METHOXYCORONARIDINE

SMILES

COCC[C@@]1([H])C[C@]2([H])C[C@]3(c4c(CCN(C2)[C@@]13[H])c5ccccc5[nH]4)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

HIDE SMILES / InChI

Molecular Formula C22H28N2O3
Molecular Weight 368.4702
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 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

PubMed

TitleDatePubMed
Time-dependent interactions between iboga agents and cocaine.
1997 Oct 8
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
Interactions between 18-methoxycoronaridine (18-MC) and cocaine: dissociation of behavioural and neurochemical sensitization.
2000 Jul 21
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
Iboga interactions with psychomotor stimulants: panacea in the paradox?
2001 Jan
Iboga compounds reverse the behavioural disinhibiting and corticosterone effects of acute methamphetamine: Implications for their antiaddictive properties.
2001 Jul-Aug
Addiction treatment strives for legitimacy.
2002 Dec 25
Modulation of nicotine self-administration in rats by combination therapy with agents blocking alpha 3 beta 4 nicotinic receptors.
2002 Jul 19
Metabolism of 18-methoxycoronaridine, an ibogaine analog, to 18-hydroxycoronaridine by genetically variable CYP2C19.
2002 Jun
Antagonism of alpha 3 beta 4 nicotinic receptors as a strategy to reduce opioid and stimulant self-administration.
2002 Mar 1
Anti-addictive actions of an iboga alkaloid congener: a novel mechanism for a novel treatment.
2003 Jun
Novel iboga alkaloid congeners block nicotinic receptors and reduce drug self-administration.
2004 May 25
Anti-HIV-1 activity of the Iboga alkaloid congener 18-methoxycoronaridine.
2004 Sep
Addiction research. Ibogaine therapy: a 'vast, uncontrolled experiment'.
2005 Apr 15
Attenuation of morphine withdrawal signs by intracerebral administration of 18-methoxycoronaridine.
2005 Nov 21
Complementary medicines in psychiatry: review of effectiveness and safety.
2006 Feb
Subtypes of neuronal nicotinic acetylcholine receptors involved in nicotine-induced phosphorylation of extracellular signal-regulated protein kinase in PC12h cells.
2006 Jan 9
18-Methoxycoronaridine acts in the medial habenula and/or interpeduncular nucleus to decrease morphine self-administration in rats.
2006 May 10
Morphine-induced changes in acetylcholine release in the interpeduncular nucleus and relationship to changes in motor behavior in rats.
2007 Jul
18-MC acts in the medial habenula and interpeduncular nucleus to attenuate dopamine sensitization to morphine in the nucleus accumbens.
2007 Jul
18-methoxycoronaridine: a potential new treatment for obesity in rats?
2008 Dec
Brain regions mediating alpha3beta4 nicotinic antagonist effects of 18-MC on methamphetamine and sucrose self-administration.
2008 Dec 3
18-Methoxycoronaridine blocks acquisition but enhances reinstatement of a cocaine place preference.
2009 Jul 17
Interaction of 18-methoxycoronaridine with nicotinic acetylcholine receptors in different conformational states.
2010 Jun
Noribogaine, but not 18-MC, exhibits similar actions as ibogaine on GDNF expression and ethanol self-administration.
2010 Oct
18-Methoxycoronaridine, a potential anti-obesity agent, does not produce a conditioned taste aversion in rats.
2010 Sep
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

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 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
Created
by admin
on Sat Jun 26 13:57:54 UTC 2021
Edited
by admin
on Sat Jun 26 13:57:54 UTC 2021
Record UNII
KX8NQX91Z8
Record Status Validated (UNII)
Record Version
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Name Type Language
18-METHOXYCORONARIDINE
Common Name English
IBOGAMINE-18-CARBOXYLIC ACID, 21-METHOXY-, METHYL ESTER
Common Name English
(-)-18-METHOXYCORONARIDINE
Common Name English
Code System Code Type Description
PUBCHEM
15479177
Created by admin on Sat Jun 26 13:57:54 UTC 2021 , Edited by admin on Sat Jun 26 13:57:54 UTC 2021
PRIMARY
CAS
308123-60-6
Created by admin on Sat Jun 26 13:57:54 UTC 2021 , Edited by admin on Sat Jun 26 13:57:54 UTC 2021
PRIMARY
EPA CompTox
308123-60-6
Created by admin on Sat Jun 26 13:57:54 UTC 2021 , Edited by admin on Sat Jun 26 13:57:54 UTC 2021
PRIMARY
DRUG BANK
DB15096
Created by admin on Sat Jun 26 13:57:54 UTC 2021 , Edited by admin on Sat Jun 26 13:57:54 UTC 2021
PRIMARY
FDA UNII
KX8NQX91Z8
Created by admin on Sat Jun 26 13:57:54 UTC 2021 , Edited by admin on Sat Jun 26 13:57:54 UTC 2021
PRIMARY
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