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Details

Stereochemistry RACEMIC
Molecular Formula C22H28N2O3
Molecular Weight 368.4693
Optical Activity ( + / - )
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Zolunicant

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

HIDE SMILES / InChI
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
Modulation of nicotine self-administration in rats by combination therapy with agents blocking alpha 3 beta 4 nicotinic receptors.
2002 Jul 19
18-methoxycoronaridine: a potential new treatment for obesity in rats?
2008 Dec
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.
Name Type Language
Zolunicant
USAN   INN  
Official Name English
(±)-18-MC
Code English
IBOGAMINE-18-CARBOXYLIC ACID, 21-METHOXY-, METHYL ESTER, (±)-
Systematic Name English
(±)-18-METHOXYCORONARIDINE
Common Name English
18-METHOXYCORONARIDINE, (±)-
Common Name English
18-MC, (±)-
Code English
ZOLUNICANT [USAN]
Common Name English
zolunicant [INN]
Common Name English
methyl (6S,6aS,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
Systematic Name English
Code System Code Type Description
CAS
188125-42-0
Created by admin on Sat Dec 16 09:47:42 GMT 2023 , Edited by admin on Sat Dec 16 09:47:42 GMT 2023
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FDA UNII
VG463BM9RL
Created by admin on Sat Dec 16 09:47:42 GMT 2023 , Edited by admin on Sat Dec 16 09:47:42 GMT 2023
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PUBCHEM
15479177
Created by admin on Sat Dec 16 09:47:42 GMT 2023 , Edited by admin on Sat Dec 16 09:47:42 GMT 2023
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NCI_THESAURUS
C188642
Created by admin on Sat Dec 16 09:47:42 GMT 2023 , Edited by admin on Sat Dec 16 09:47:42 GMT 2023
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WIKIPEDIA
18-Methoxycoronaridine
Created by admin on Sat Dec 16 09:47:42 GMT 2023 , Edited by admin on Sat Dec 16 09:47:42 GMT 2023
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USAN
HI-214
Created by admin on Sat Dec 16 09:47:42 GMT 2023 , Edited by admin on Sat Dec 16 09:47:42 GMT 2023
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INN
11905
Created by admin on Sat Dec 16 09:47:42 GMT 2023 , Edited by admin on Sat Dec 16 09:47:42 GMT 2023
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SMS_ID
300000044768
Created by admin on Sat Dec 16 09:47:42 GMT 2023 , Edited by admin on Sat Dec 16 09:47:42 GMT 2023
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