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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H28N2O3.ClH
Molecular Weight 404.93
Optical Activity ( - )
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Zolunicant hydrochloride, (-)-

SMILES

Cl.[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=CVBFKKVQGICEBT-BWXWGAIDSA-N
InChI=1S/C22H28N2O3.ClH/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;1H/t14-,15+,20+,22-;/m1./s1

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C22H28N2O3
Molecular Weight 368.4693
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
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
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
Subtypes of neuronal nicotinic acetylcholine receptors involved in nicotine-induced phosphorylation of extracellular signal-regulated protein kinase in PC12h cells.
2006 Jan 9
Morphine-induced changes in acetylcholine release in the interpeduncular nucleus and relationship to changes in motor behavior in rats.
2007 Jul
18-Methoxycoronaridine blocks acquisition but enhances reinstatement of a cocaine place preference.
2009 Jul 17
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 Dec 16 10:07:18 GMT 2023
Edited
by admin
on Sat Dec 16 10:07:18 GMT 2023
Record UNII
85Z0P8329N
Record Status Validated (UNII)
Record Version
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Name Type Language
Zolunicant hydrochloride, (-)-
Common Name English
IBOGAMINE-18-CARBOXYLIC ACID, 21-METHOXY-, METHYL ESTER, HYDROCHLORIDE (1:1)
Systematic Name English
(-)-18-METHOXYCORONARIDINE HYDROCHLORIDE
Common Name English
IBOGAMINE-18-CARBOXYLIC ACID, 21-METHOXY-, METHYL ESTER, MONOHYDROCHLORIDE
Common Name English
18-METHOXYCORONARIDINE HYDROCHLORIDE
Common Name English
Code System Code Type Description
FDA UNII
85Z0P8329N
Created by admin on Sat Dec 16 10:07:18 GMT 2023 , Edited by admin on Sat Dec 16 10:07:18 GMT 2023
PRIMARY
CAS
266686-77-5
Created by admin on Sat Dec 16 10:07:18 GMT 2023 , Edited by admin on Sat Dec 16 10:07:18 GMT 2023
PRIMARY
PUBCHEM
76960565
Created by admin on Sat Dec 16 10:07:18 GMT 2023 , Edited by admin on Sat Dec 16 10:07:18 GMT 2023
PRIMARY
Related Record Type Details
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PARENT -> SALT/SOLVATE