U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
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 RACEMIC
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
Iboga interactions with psychomotor stimulants: panacea in the paradox?
2001 Jan
Modulation of nicotine self-administration in rats by combination therapy with agents blocking alpha 3 beta 4 nicotinic receptors.
2002 Jul 19
Antagonism of alpha 3 beta 4 nicotinic receptors as a strategy to reduce opioid and stimulant self-administration.
2002 Mar 1
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
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 09:47:45 GMT 2023
Edited
by admin
on Sat Dec 16 09:47:45 GMT 2023
Record UNII
LN5K0F4GJF
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Zolunicant hydrochloride
USAN  
Official Name English
ZOLUNICANT HYDROCHLORIDE [USAN]
Common Name English
(±)-18-MC HYDROCHLORIDE
Code English
(1RS,13RS,17SR)-1-(METHOXYCARBONYL)-17-(2-METHOXYETHYL)-3,13-DIAZAPENTACYCLO(13.3.1.0^2,10^.0^4,9^.0^13,18^)NONADECA-2(10),4,6,8-TETRAEN-13-IUM CHLORIDE
Systematic Name English
RAC-18-METHOXYCORONARIDINE HYDROCHLORIDE
Common Name English
18-METHOXYCORONARIDINE HYDROCHLORIDE, (±)-
Common Name English
6,9-METHANO-5H-PYRIDO(1',2':1,2)AZEPINO(4,5-B)INDOLE-6(6AH)-CARBOXYLIC ACID, 7,8,9,10,12,13-HEXAHYDRO-7-(2-METHOXYETHYL)-, METHYL ESTER, HYDROCHLORIDE (1:1), (6R,6AR,7S,9S,11R)-REL-
Systematic Name English
methyl (6s,7r,9r,11s)-7-(2-methoxyethyl)-7,8,9,10,12,13-hexahydro-5H-6,9- methanopyrido[1',2':1,2]azepino[4,5-b]indole-6(6aH)-carboxylate, chloride salt (1:1)
Systematic Name English
Code System Code Type Description
FDA UNII
LN5K0F4GJF
Created by admin on Sat Dec 16 09:47:45 GMT 2023 , Edited by admin on Sat Dec 16 09:47:45 GMT 2023
PRIMARY
PUBCHEM
76960565
Created by admin on Sat Dec 16 09:47:45 GMT 2023 , Edited by admin on Sat Dec 16 09:47:45 GMT 2023
PRIMARY
SMS_ID
300000044769
Created by admin on Sat Dec 16 09:47:45 GMT 2023 , Edited by admin on Sat Dec 16 09:47:45 GMT 2023
PRIMARY
NCI_THESAURUS
C188594
Created by admin on Sat Dec 16 09:47:45 GMT 2023 , Edited by admin on Sat Dec 16 09:47:45 GMT 2023
PRIMARY
CAS
1388145-90-1
Created by admin on Sat Dec 16 09:47:45 GMT 2023 , Edited by admin on Sat Dec 16 09:47:45 GMT 2023
PRIMARY
USAN
HI-215
Created by admin on Sat Dec 16 09:47:45 GMT 2023 , Edited by admin on Sat Dec 16 09:47:45 GMT 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY