Coronaridine

Coronaridine

Clinical data
ATC code	none
Identifiers
IUPAC name methyl (1S,15R,17S,18S)-17-ethyl-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate
CAS Number	467-77-6
PubChem CID	6426909
ChemSpider	4932328
ECHA InfoCard	100.006.727
Chemical and physical data
Formula	C21H26N2O2
Molar mass	338.44 g/mol
3D model (Jmol)	Interactive image
SMILES CCC1CC2CC3(C1N(C2)CCC4=C3NC5=CC=CC=C45)C(=O)OC
InChI InChI=1S/C21H26N2O2/c1-3-14-10-13-11-21(20(24)25-2)18-16(8-9-23(12-13)19(14)21)15-6-4-5-7-17(15)22-18/h4-7,13-14,19,22H,3,8-12H2,1-2H3/t13-,14+,19+,21-/m1/s1 Key:NVVDQMVGALBDGE-PZXGUROGSA-N

Coronaridine, also known as 18-carbomethoxyibogamine, is an alkaloid found in Tabernanthe iboga and related species,including Tabernaemontana divaricata for which (under the now obsolete synonym Ervatamia coronaria) it was named.

Coronaridine persistently reduces the self-administration of cocaine and morphine in rats.

Coronaridine has been reported to bind to an assortment of molecular sites, including: μ-opioid (K_i = 2.0 μM), δ-opioid (K_i = 8.1 μM), and κ-opioid receptors (K_i = 4.3 μM), NMDA receptor (K_i = 6.24 μM) (as an antagonist), and nAChRs (as an antagonist). It has also been found to inhibit the enzyme acetylcholinesterase, act as a voltage-gated sodium channel blocker, and displays estrogenic activity in rodents. In contrast to ibogaine and other iboga alkaloids, coronaridine does not bind to either the σ₁ or σ₂ receptor. Coronaridine also has estrogenic properties.