Coronaridine

Coronaridine, also known as 18-carbomethoxyibogamine, is an

alkaloid found in Tabernanthe iboga and related species, including
Coronaridine
Tabernaemontana divaricata for which (under the now obsolete
synonym Ervatamia coronaria) it was named.[1]

Like ibogaine, (R)-coronaridine and (S)-coronaridine can decrease

intake of cocaine and morphine intake in animals[2] and it may
have muscle relaxant and hypotensive activity.[3]

Contents
Chemistry
Congeners
Pharmacology
Sources
See also Clinical data

References ATC code none

Identifiers

Chemistry IUPAC name

Methyl (1S,15R,17S,18S)-17-ethyl-
3,13-diazapentacyclo[13.3.1.0 2,1
Congeners 0.0 4,9.0 13,18]nonadeca-2(10),4,6,

8-tetraene-1-carboxylate
Coronaridine congers are important in drug discovery and
CAS 467-77-6 (https://co
development due to multiple actions on different targets. They Number
have ability to inhibit Cav 2.2 channel,[4] modulate and inhibit mmonchemistry.cas.
subunits of nAChr selectively such as α9α10,[4] α3β4[5][6] and org/detail?cas_rn=46
potentiate GABAA activity.[7] 7-77-6)
PubChem 6426909 (https://pub
CID
Pharmacology chem.ncbi.nlm.nih.go
v/compound/642690
Coronaridine has been reported to bind to an assortment of 9)
molecular sites, including: μ-opioid (Ki = 2.0 μM), δ-opioid (Ki = ChemSpider 4932328 (https://ww
8.1 μM), and κ-opioid receptors (Ki = 4.3 μM), NMDA receptor w.chemspider.com/C
(Ki = 6.24 μM) (as an antagonist),[8] and nAChRs (as an hemical-Structure.49
antagonist).[9] It has also been found to inhibit the enzyme 32328.html)
acetylcholinesterase, act as a voltage-gated sodium channel
ChEBI CHEBI:3887 (https://
blocker,[10] and displays estrogenic activity in rodents.[8][9] In
contrast to ibogaine and other iboga alkaloids, coronaridine does www.ebi.ac.uk/chebi/
not bind to either the σ1 or σ2 receptor.[10]
 searchId.do?chebiId
Sources
=CHEBI:3887)
Plant sources CompTox DTXSID60963642 (h
Dashboard
Family Plants ttps://comptox.epa.g
(EPA)
T. catharinensis, T. ternifolia, T. pandacaqui, T.
ov/dashboard/chemi
Apocynaceae heyneana, T. litoralis, T. divaricata, T. cal/details/DTXSID60
penduliflora.[11] 963642)
ECHA 100.006.727 (https://
See also InfoCard echa.europa.eu/subs
tance-information/-/s
Dregamine ubstanceinfo/100.00
Ibogaine 6.727)
Ibogamine
Chemical and physical data
Tabernanthine
Formula C21H26N2O2
Voacangine
Molar mass 338.451 g·mol−1

References 3D model
(JSmol)
Interactive image (htt
ps://chemapps.stolaf.
1. Delorenzi JC, Freire-de-Lima L, Gattass CR, et al. (July edu/jmol/jmol.php?m
2002). "In vitro activities of iboga alkaloid congeners
odel=CCC1CC2CC
coronaridine and 18-methoxycoronaridine against
3%28C1N%28C2%2
Leishmania amazonensis" (https://www.ncbi.nlm.nih.go
v/pmc/articles/PMC127312). Antimicrobial Agents and 9CCC4%3DC3NC5%
Chemotherapy. 46 (7): 2111–5. 3DCC%3DCC%3DC
doi:10.1128/aac.46.7.2111-2115.2002 (https://doi.org/1 45%29C%28%3DO%
0.1128%2Faac.46.7.2111-2115.2002). PMC 127312 (htt 29OC)
ps://www.ncbi.nlm.nih.gov/pmc/articles/PMC127312).
SMILES
PMID 12069962 (https://pubmed.ncbi.nlm.nih.gov/1206
9962). CCC1CC2CC3(C1N(C2)CCC4=C3
NC5=CC=CC=C45)C(=O)OC
2. Spinella, Marcello (2001). The Psychopharmacology of
Herbal Medicine: Plant Drugs that Alter Mind, Brain, and InChI
Behavior (https://books.google.com/books?id=jZeaRiIF InChI=1S/C21H26N2O2/c1-3-14-10
bhsC&q=desethylcoronaridine&pg=PA370). The MIT -13-11-21(20(24)25-2)18-16(8-9
-23(12-13)19(14)21)15-6-4-5-7-
Press; Illustrated edition. ISBN 978-0262692656.
17(15)22-18/h4-7,13-14,19,22H,
3. Perera, Premila; Kanjanapothy, Duangta; Sandberg, 3,8-12H2,1-2H3/t13-,14+,19+,21
Finn; Verpoorte, Robert (1985). "Muscle relaxant activity -/m1/s1
and hypotensive activity of some tabernaemontana Key:NVVDQMVGALBDGE-PZXGUR
alkaloids". Journal of Ethnopharmacology. 13 (2): 165– OGSA-N
173. doi:10.1016/0378-8741(85)90004-2 (https://doi.org/
10.1016%2F0378-8741%2885%2990004-2).
PMID 4021514 (https://pubmed.ncbi.nlm.nih.gov/40215
14).
4. Arias HR, Tae HS, Micheli L, Yousuf A, Ghelardini C,
Adams DJ, Di Cesare Mannelli L (September 2020).
"Coronaridine congeners decrease neuropathic pain in
mice and inhibit α9α10 nicotinic acetylcholine receptors
and CaV2.2 channels". Neuropharmacology. 175:
108194. doi:10.1016/j.neuropharm.2020.108194 (https://
doi.org/10.1016%2Fj.neuropharm.2020.108194).
hdl:2158/1213504 (https://hdl.handle.net/2158%2F1213
504). PMID 32540451 (https://pubmed.ncbi.nlm.nih.gov/
32540451). S2CID 219705597 (https://api.semanticscho
lar.org/CorpusID:219705597).
5. Arias HR, Targowska-Duda KM, Feuerbach D, Jozwiak
K (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. 65:
81–90. doi:10.1016/j.biocel.2015.05.015 (https://doi.org/
10.1016%2Fj.biocel.2015.05.015). PMID 26022277 (htt
ps://pubmed.ncbi.nlm.nih.gov/26022277).
6. Arias HR, Lykhmus O, Uspenska K, Skok M (March
2018). "Coronaridine congeners modulate mitochondrial
α3β4* nicotinic acetylcholine receptors with different
potency and through distinct intra-mitochondrial
pathways". Neurochemistry International. 114: 26–32.
doi:10.1016/j.neuint.2017.12.008 (https://doi.org/10.101
6%2Fj.neuint.2017.12.008). PMID 29277577 (https://pu
bmed.ncbi.nlm.nih.gov/29277577). S2CID 3675707 (htt
ps://api.semanticscholar.org/CorpusID:3675707).
7. Arias HR, Do Rego JL, Do Rego JC, Chen Z, Anouar Y,
Scholze P, Gonzales EB, Huang R, Chagraoui A (July
2020). "Coronaridine congeners potentiate GABAA
receptors and induce sedative activity in mice in a
benzodiazepine-insensitive manner" (https://hal.archive
s-ouvertes.fr/hal-03489760/file/S027858461931019X.p
df) (PDF). Progress in Neuro-psychopharmacology &
Biological Psychiatry. 101: 109930.
doi:10.1016/j.pnpbp.2020.109930 (https://doi.org/10.101
6%2Fj.pnpbp.2020.109930). PMID 32194202 (https://pu
bmed.ncbi.nlm.nih.gov/32194202). S2CID 212734631
(https://api.semanticscholar.org/CorpusID:212734631).
8. Christophe Wiart (16 December 2013). Lead
Compounds from Medicinal Plants for the Treatment of
Neurodegenerative Diseases (https://books.google.com/
books?id=o3opAgAAQBAJ&pg=PA67). Academic
Press. pp. 67–69, 73. ISBN 978-0-12-398383-1.
9. Gideon Polya (15 May 2003). Biochemical Targets of
Plant Bioactive Compounds: A Pharmacological
Reference Guide to Sites of Action and Biological
Effects (https://books.google.com/books?id=Q20_AJ3w
QOoC&pg=PA203). CRC Press. pp. 203–. ISBN 978-0-
203-01371-7.
10. Chemistry and Biology (https://books.google.com/book
s?id=bE503LRsawYC&pg=PA222). Academic Press.
21 September 1998. pp. 222–. ISBN 978-0-08-086576-
8.
11. European Bioinformatics Institute (https://www.ebi.ac.uk/
chebi/searchId.do?chebiId=CHEBI:3887)

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