Coronaridine

Coronaridine

Systematic (IUPAC) name
Ibogamine-18-carboxylic acid methyl ester
Identifiers
CAS Number	467-77-6
ATC code	none
PubChem	CID: 73489
ChemSpider	4932328
ChEMBL	CHEMBL364613
Chemical data
Formula	C21H26N2O2
Molecular mass	338.44 g/mol
SMILES CC[C@H]1C[C@@H]2C[C@@]3([C@H]1N(C2)CCc4c3[nH]c5c4cccc5)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.

Pharmacology

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.

See also

• Ibogaine
• Ibogamine
• Tabernanthine
• Voacangine