Coronaridine

Chemical compound From Wikipedia, the free encyclopedia

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]

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  • none
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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
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ChEBI
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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
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Like ibogaine, (R)-coronaridine and (S)-coronaridine can decrease intake of cocaine and morphine in animals[2] and it may have muscle relaxant and hypotensive activity.[3]

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,[4] modulate and inhibit subunits of nAChr selectively such as α9α10,[4] α3β4[5][6] and potentiate GABAA activity.[7]

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),[8] and nAChRs (as an antagonist).[9] It has also been found to inhibit the enzyme acetylcholinesterase, act as a voltage-gated sodium channel blocker,[10] and displays estrogenic activity in rodents.[8][9] In contrast to ibogaine and other iboga alkaloids, coronaridine does not bind to either the σ1 or σ2 receptor.[10]

Sources

More information Family, Plants ...
Plant sources
FamilyPlants
ApocynaceaeT. catharinensis, T. ternifolia, T. pandacaqui, T. heyneana, T. litoralis, T. divaricata, T. penduliflora.[11]
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See also

References

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