| Identification | Back Directory | [Name]
methyl ibogamine-18-carboxylate | [CAS]
467-77-6 | [Synonyms]
NSC 127490
Coronaridin
coronardine
methyl ibogamine-18-carboxylate
Ibogamine-18-carboxylic acid methyl ester
(-)-Ibogamine-18-carboxylic acid methyl ester | [EINECS(EC#)]
207-398-7 | [Molecular Formula]
C21H26N2O2 | [MDL Number]
MFCD11111278 | [MOL File]
467-77-6.mol | [Molecular Weight]
338.448 |
| Chemical Properties | Back Directory | [Melting point ]
92-93 °C | [Boiling point ]
488.1±45.0 °C(Predicted) | [density ]
1.24±0.1 g/cm3(Predicted) | [storage temp. ]
4°C, protect from light | [form ]
Solid | [pka]
16?+-.0.60(Predicted) | [color ]
White to off-white |
| Hazard Information | Back Directory | [Uses]
Ibogamine-18-carboxylic Acid Methyl Ester (CAS# 467-77-6) is a useful research chemical compound. It is used in the biosynthesis of anti-addiction agent from iboga plant. | [Definition]
ChEBI: (-)-coronaridine is a monoterpenoid indole alkaloid with formula C21H26N2O2. It is isolated from the flowering plant genus, Tabernaemontana. It has a role as an antileishmanial agent, an antineoplastic agent, an apoptosis inducer and a plant metabolite. It is a monoterpenoid indole alkaloid, a methyl ester, an organic heteropentacyclic compound and an alkaloid ester. It is a conjugate base of a (-)-coronaridine(1+). | [Biological Activity]
Coronaridine, an iboga type alkaloid, inhibits the wnt signaling pathway by decreasing β-catenin expression[1].
Coronaridine (0-40 μM; 24 hours) is against non-cancer cells with IC50 values >40 μM. It agaisnt wnt-dependent cells with IC50 values of 10.4, 11.6 and 24.4 μM for SW480, HCT116 and DLD1cells, respectively[1].Coronaridine (0-40 μM; 24 hours) inhibits β-catenin expression, but the protein levels of p-β--catenin at Ser33, Ser37, and Thr41 and p-β-catenin at Ser 45 [p-b-catenin (S45)] are unchanged[1].In whole-cell patch clamp recordings,Catharanthine (1-300 μM) are respectively co-applied with GABA at concentrations corresponding to the EC30 value for each receptor subtype. Both congeners potentiated different GABAARs in a concentration-dependent manner[2].At higher concentrations, however, Catharanthine starts to inhibit GABA-activated currents due to the reduced amplitude and rebound current, where the threshold concentration depended on the receptor subtype (e.g., > 30 μM for hα1β2; > 100 μM for hα1β2γ2 and hα2β2γ2). The PAM activity of Catharanthine's are depended on the receptor subtype: hα1β2 (4.6±0.8 μM), >hα2β2γ2 (12.6±3.8 μM), hα1β2γ2 (14.4 ± 4.6 μM)[2]. | [References]
[1]. Kensuke Ohishi, et al. Coronaridine, an iboga type alkaloid from Tabernaemontana divaricata, inhibits the Wnt signaling pathway by decreasing β-catenin mRNA expression. Bioorg Med Chem Lett. 2015 Sep 15;25(18):3937-40. [2]. Hugo R Arias, et al. Coronaridine congeners potentiate GABA A receptors and induce sedative activity in mice in a benzodiazepine-insensitive manner. Prog Neuropsychopharmacol Biol Psychiatry. 2020 Jul 13;101:109930 |
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