Coronaridine

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title: "Coronaridine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["acetylcholinesterase-inhibitors", "alkaloids", "alkaloids-found-in-iboga", "carboxylate-esters", "ethers", "nicotinic-antagonists", "nmda-receptor-antagonists", "opioids", "phytoestrogens", "sodium-channel-blockers"] description: "Chemical compound" topic_path: "general/acetylcholinesterase-inhibitors" source: "https://en.wikipedia.org/wiki/Coronaridine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| 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 | image = Coronaridine.svg | image_class = skin-invert-image | alt = Skeletal formula of coronaridine | image2 = Coronaridine molecule ball.png | image_class2 = bg-transparent | alt2 = Ball-and-stick model of the coronaridine molecule

| tradename = | pregnancy_category = | legal_status = | routes_of_administration =

| bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =

| CAS_number = 467-77-6 | ATC_prefix = none | ATC_suffix = | PubChem = 6426909 | ChemSpiderID = 4932328 | ChEBI = 3887 | ChEMBL =

| C=21 | H=26 | N=2 | O=2 | smiles = CCC1CC2CC3(C1N(C2)CCC4=C3NC5=CC=CC=C45)C(=O)OC | StdInChI = 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 | StdInChIKey = 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.

Like ibogaine, (R)-coronaridine and (S)-coronaridine can decrease intake of cocaine and morphine in animals and it may have muscle relaxant and hypotensive activity.

Chemistry

Congeners

Coronaridine congers are important in drug discovery and development due to multiple actions on different targets. They have ability to inhibit Cav2.2 channel, modulate and inhibit subunits of nAChr selectively such as α9α10, α3β4 and potentiate GABAA activity.

Pharmacology

Coronaridine has been reported to bind to an assortment of molecular sites, including: μ-opioid (Ki = 2.0 μM), δ-opioid (Ki = 8.1 μM), and κ-opioid receptors (Ki = 4.3 μM), NMDA receptor (Ki = 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.

Sources

::data[format=table title="Plant sources"]

Family	Plants
Apocynaceae	T. catharinensis, T. ternifolia, T. pandacaqui, T. heyneana, T. litoralis, T. divaricata, T. penduliflora.
::

References

References

1. (July 2002). "In vitro activities of iboga alkaloid congeners coronaridine and 18-methoxycoronaridine against Leishmania amazonensis". Antimicrobial Agents and Chemotherapy.
2. (2001). "The Psychopharmacology of Herbal Medicine: Plant Drugs that Alter Mind, Brain, and Behavior". The MIT Press; Illustrated edition.
3. (May 1985). "Muscle relaxant activity and hypotensive activity of some Tabernaemontana alkaloids". Journal of Ethnopharmacology.
4. (September 2020). "Coronaridine congeners decrease neuropathic pain in mice and inhibit α9α10 nicotinic acetylcholine receptors and CaV2.2 channels". [[Neuropharmacology]].
5. (August 2015). "Coronaridine congeners inhibit human α3β4 nicotinic acetylcholine receptors by interacting with luminal and non-luminal sites". [[The International Journal of Biochemistry & Cell Biology]].
6. (March 2018). "Coronaridine congeners modulate mitochondrial α3β4* nicotinic acetylcholine receptors with different potency and through distinct intra-mitochondrial pathways". [[Neurochemistry International]].
7. (July 2020). "Coronaridine congeners potentiate GABAA receptors and induce sedative activity in mice in a benzodiazepine-insensitive manner". [[Progress in Neuro-psychopharmacology & Biological Psychiatry]].
8. (16 December 2013). "Lead Compounds from Medicinal Plants for the Treatment of Neurodegenerative Diseases". Academic Press.
9. (15 May 2003). "Biochemical Targets of Plant Bioactive Compounds: A Pharmacological Reference Guide to Sites of Action and Biological Effects". CRC Press.
10. (1999). "The Alkaloids. Chemistry and Biology". Academic Press.
11. "(−)-Coronaridine". European Bioinformatics Institute.

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::