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Coronaridine

Coronaridine
Skeletal formula of coronaridine
Ball-and-stick model of the coronaridine molecule
Clinical data
ATC code
  • none
Identifiers
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
ECHA InfoCard100.006.727 Edit this at Wikidata
Chemical and physical data
FormulaC21H26N2O2
Molar mass338.44 g/mol g·mol−1
3D model (JSmol)

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]

Coronaridine persistently reduces the self-administration of cocaine and morphine in rats.[2]

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),[3] and nAChRs (as an antagonist).[4] It has also been found to inhibit the enzyme acetylcholinesterase, act as a voltage-gated sodium channel blocker,[5] and displays estrogenic activity in rodents.[3][4] In contrast to ibogaine and other iboga alkaloids, coronaridine does not bind to either the σ1 or σ2 receptor.[5] Coronaridine also has estrogenic properties.[3]

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. ^ Glick SD, Kuehne ME, Raucci J, Wilson TE, Larson D, Keller RW Jr, Carlson JN (September 1994). "Effects of iboga alkaloids on morphine and cocaine self-administration in rats: relationship to tremorigenic effects and to effects on dopamine release in nucleus accumbens and striatum". Brain Res. 657 (1–2): 14–22. doi:10.1016/0006-8993(94)90948-2. PMID 7820611.
  3. ^ a b c 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.
  4. ^ 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.
  5. ^ a b Chemistry and Biology. Academic Press. 21 September 1998. pp. 222–. ISBN 978-0-08-086576-8.