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Coronaridine

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
PubChem CID
ChemSpider
ChEBI
CompTox Dashboard (EPA)
ECHA InfoCard100.006.727 Edit 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 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.[1]

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),[2] and nAChRs (as an antagonist).[3] It has also been found to inhibit the enzyme acetylcholinesterase, act as a voltage-gated sodium channel blocker,[4] and displays estrogenic activity in rodents.[2][3] In contrast to ibogaine and other iboga alkaloids, coronaridine does not bind to either the σ1 or σ2 receptor.[4]

Sources

Plant sources
Family Plants
Apocynaceae Tabernaemontana catharinensis, Tabernaemontana ternifolia, Tabernaemontana pandacaqui, Tabernaemontana heyneana, Tabernaemontana litoralis, Tabernaemontana divaricata, Tabernaemontana penduliflora.[5]

See also

References

  1. ^ Delorenzi JC, Freire-de-Lima L, Gattass CR, et al. (July 2002). "In vitro activities of iboga alkaloid congeners coronaridine and 18-methoxycoronaridine against Leishmania amazonensis". Antimicrobial Agents and Chemotherapy. 46 (7): 2111–5. doi:10.1128/aac.46.7.2111-2115.2002. PMC 127312. PMID 12069962.
  2. ^ a b Christophe Wiart (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.
  3. ^ a b Gideon Polya (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.
  4. ^ a b Chemistry and Biology. Academic Press. 21 September 1998. pp. 222–. ISBN 978-0-08-086576-8.
  5. ^ European Bioinformatics Institute


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