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Coronaridine

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Coronaridine
Skeletal formula of coronaridine
Ball-and-stick model of the coronaridine molecule
Clinical data
ATC code
  • none
Identifiers
  • 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
PubChemCID
ChemSpider
ChEBI
CompTox Dashboard(EPA)
ECHA InfoCard100.006.727Edit this at Wikidata
Chemical and physical data
FormulaC21H26N2O2
Molar mass338.451 g·mol−1
3D model (JSmol)
  • CCC1CC2CC3(C1N(C2)CCC4=C3NC5=CC=CC=C45)C(=O)OC
  • 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 as18-carbomethoxyibogamine, is analkaloid found inTabernanthe iboga and related species, includingTabernaemontana divaricata for which (under the now obsolete synonymErvatamia coronaria) it was named.[1]

Likeibogaine, (R)-coronaridine and (S)-coronaridine can decrease intake of cocaine and morphine in animals[2] and it may havemuscle relaxant andhypotensive activity.[3]

Chemistry

[edit]

Congeners

[edit]

Coronaridine congers are important in drug discovery and development due to multiple actions on different targets. They have ability to inhibitCav2.2 channel,[4] modulate and inhibit subunits of nAChr selectively such as α9α10,[4]α3β4[5][6] and potentiateGABAA activity.[7]

Pharmacology

[edit]

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), andκ-opioid receptors (Ki = 4.3 μM),NMDA receptor (Ki = 6.24 μM) (as anantagonist),[8] andnAChRs (as an antagonist).[9] It has also been found to inhibit the enzymeacetylcholinesterase, act as avoltage-gated sodium channelblocker,[10] and displaysestrogenic activity in rodents.[8][9] In contrast toibogaine and otheriboga alkaloids, coronaridine does not bind to either theσ1 orσ2 receptor.[10]

Sources

[edit]
Plant sources
FamilyPlants
ApocynaceaeT. catharinensis,T. ternifolia,T. pandacaqui,T. heyneana,T. litoralis,T. divaricata,T. penduliflora.[11]

See also

[edit]

References

[edit]
  1. ^Delorenzi JC, Freire-de-Lima L, Gattass CR, de Andrade Costa D, He L, Kuehne ME, Saraiva EM (July 2002)."In vitro activities of iboga alkaloid congeners coronaridine and 18-methoxycoronaridine against Leishmania amazonensis".Antimicrobial Agents and Chemotherapy.46 (7):2111–2115.doi:10.1128/aac.46.7.2111-2115.2002.PMC 127312.PMID 12069962.
  2. ^Spinella M (2001).The Psychopharmacology of Herbal Medicine: Plant Drugs that Alter Mind, Brain, and Behavior. The MIT Press; Illustrated edition.ISBN 978-0262692656.
  3. ^Perera P, Kanjanapothy D, Sandberg F, Verpoorte R (May 1985). "Muscle relaxant activity and hypotensive activity of some Tabernaemontana alkaloids".Journal of Ethnopharmacology.13 (2):165–173.doi:10.1016/0378-8741(85)90004-2.PMID 4021514.
  4. ^abArias 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.hdl:2158/1213504.PMID 32540451.S2CID 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.PMID 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.PMID 29277577.S2CID 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"(PDF).Progress in Neuro-psychopharmacology & Biological Psychiatry.101 109930.doi:10.1016/j.pnpbp.2020.109930.PMID 32194202.S2CID 212734631.
  8. ^abWiart C (16 December 2013).Lead Compounds from Medicinal Plants for the Treatment of Neurodegenerative Diseases. Academic Press. pp. 67–69, 73.ISBN 978-0-12-398383-1.
  9. ^abPolya G (15 May 2003).Biochemical Targets of Plant Bioactive Compounds: A Pharmacological Reference Guide to Sites of Action and Biological Effects. CRC Press. pp. 203–.ISBN 978-0-203-01371-7.
  10. ^abPopik P, Skolnick P (1999)."Pharmacology of Ibogaine and Ibogaine-Related Alkaloids". In Cordell GA (ed.).The Alkaloids. Chemistry and Biology. Vol. 52. San Diego: Academic Press. pp. 197–232 (222).ISBN 978-0-08-086576-8.
  11. ^"(−)-Coronaridine".ChEBI. European Bioinformatics Institute. CHEBI:3887.
Drugs used in treatment ofdrug dependence (N07B)
Nicotine dependence
Alcohol dependence
Opioid dependence
Benzodiazepine dependence
Enzyme
(modulators)
ChATTooltip Choline acetyltransferase
AChETooltip Acetylcholinesterase
BChETooltip Butyrylcholinesterase
Transporter
(modulators)
CHTTooltip Choline transporter
VAChTTooltip Vesicular acetylcholine transporter
Release
(modulators)
Inhibitors
Enhancers
ERTooltip Estrogen receptor
Agonists
Mixed
(SERMsTooltip Selective estrogen receptor modulators)
Antagonists
GPERTooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown
Calcium
VDCCsTooltip Voltage-dependent calcium channels
Blockers
Activators
Potassium
VGKCsTooltip Voltage-gated potassium channels
Blockers
Activators
IRKsTooltip Inwardly rectifying potassium channel
Blockers
Activators
KCaTooltip Calcium-activated potassium channel
Blockers
Activators
K2PsTooltip Tandem pore domain potassium channel
Blockers
Activators
Sodium
VGSCsTooltip Voltage-gated sodium channels
Blockers
Activators
ENaCTooltip Epithelial sodium channel
Blockers
Activators
ASICsTooltip Acid-sensing ion channel
Blockers
Chloride
CaCCsTooltip Calcium-activated chloride channel
Blockers
Activators
CFTRTooltip Cystic fibrosis transmembrane conductance regulator
Blockers
Activators
Unsorted
Blockers
Others
TRPsTooltip Transient receptor potential channels
LGICsTooltip Ligand gated ion channels
AMPARTooltip α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor
KARTooltip Kainate receptor
NMDARTooltip N-Methyl-D-aspartate receptor
nAChRsTooltip Nicotinic acetylcholine receptors
Agonists
(andPAMsTooltip positive allosteric modulators)
Antagonists
(andNAMsTooltip negative allosteric modulators)
Precursors
(andprodrugs)
μ-opioid
(MOR)
Agonists
(abridged;
full list)
Antagonists
δ-opioid
(DOR)
Agonists
Antagonists
κ-opioid
(KOR)
Agonists
Antagonists
Nociceptin
(NOP)
Agonists
Antagonists
Others
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