308123-60-6
Chemical Structure
18-Methoxycoronaridine
Synonym(s): (-)-18-Methoxycoronaridine
- CAS No.: 308123-60-6
- Formula:C22H28N2O3
- Molecular Weight:368.48
IUPAC Name: 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
InChIKey: DTJQBBHYRQYDEG-SVBQBFEESA-N
SMILES: C(OC)(=O)[C@]12[C@]3([N@](C[C@@](C1)(C[C@@H]3CCOC)[H])CCC4=C2NC=5C4=CC=CC5)[H]
Biological Activity: 18-Methoxycoronaridine ((-)-18-Methoxycoronaridine) is an orally active and selective α3β4 nicotinic acetylcholine receptor (nAChR) antagonist. 18-Methoxycoronaridine is an inhibitor of serotonin transporter (SERT) and norepinephrine transporter (NET), with IC50 values of 51.6 μM and 121 μM for SERT and NET, respectively. 18-Methoxycoronaridine inhibits the function of SERT and NET, promotes 5-HT3A receptor desensitization, blocks α3β4 nAChR, and modulates receptor signaling pathways associated with reinforcement. 18-Methoxycoronaridine also exhibits potent antiparasitic activity. 18-Methoxycoronaridine can be used in research related to depression, obesity, alcoholism, smoking addiction, and cutaneous leishmaniasis[1][2][3][4][5][6].
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18-Methoxycoronaridine | 18-Methoxycoronaridine ((-)-18-Methoxycoronaridine) is an orally active and selective α3β4 nicotinic acetylcholine receptor (nAChR) antagonist. 18-Methoxycoronaridine is an inhibitor of serotonin transporter (SERT) and norepinephrine transporter (NET), with IC50 values of 51.6 μM and 121 μM for SERT and NET, respectively. 18-Methoxycoronaridine inhibits the function of SERT and NET, promotes 5-HT3A receptor desensitization, blocks α3β4 nAChR, and modulates receptor signaling pathways associated with reinforcement. 18-Methoxycoronaridine also exhibits potent antiparasitic activity. 18-Methoxycoronaridine can be used in research related to depression, obesity, alcoholism, smoking addiction, and cutaneous leishmaniasis. | |||||||||||||||||||||
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References
- [1]. Zhang W, et al. Metabolism of 18-methoxycoronaridine, an ibogaine analog, to 18-hydroxycoronaridine by genetically variable CYP2C19. Drug metabolism and disposition: the biological fate of chemicals. 2002 Jun;30(6):663-9.
- [2]. Arias HR, et al. (+)-Catharanthine and (-)-18-methoxycoronaridine induce antidepressant-like activity in mice by differently recruiting serotonergic and norepinephrinergic neurotransmission. European journal of pharmacology. 2023 Jan 15;939:175454. [Content Brief]
- [3]. Taraschenko OD, et al. 18-Methoxycoronaridine, a potential anti-obesity agent, does not produce a conditioned taste aversion in rats. Pharmacology, biochemistry, and behavior. 2010 Sep;96(3):247-50.
- [4]. Rezvani AH, et al. Acute oral 18-methoxycoronaridine (18-MC) decreases both alcohol intake and IV nicotine self-administration in rats. Pharmacology, biochemistry, and behavior. 2016;150-151:153-157.
- [5]. Delorenzi JC, et al. Oral 18-methoxycoronaridine activity in simian and murine Leishmania amazonensis infection. Front Pharmacol. 2026 Apr 10;17:1780255. [Content Brief]
- [6]. Miller CN, et al. The α3β4 nicotinic acetylcholine receptor antagonist 18-Methoxycoronaridine decreases binge-like ethanol consumption in adult C57BL/6J mice. Alcohol. 2019 Sep;79:1-6. [Content Brief]
