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Eugenol is one of many potential metabolites of Caleicine and the mechanisms of both Caleicine and Calea Ternifolia are largely misunderstood.
Eugenol is one of many potential metabolites of Caleicine and the mechanisms of both Caleicine and Calea Ternifolia are largely misunderstood.


== See also ==

* [[GABA receptor]]
* [[Germacranolide|Germacranolides]]
* [[Myristicin]]


== References ==
== References ==

Revision as of 09:32, 3 November 2024

Caleicine
Skeletal formula of Caleicine
3D model of Caleicine
Legal status
Legal status
  • In general: uncontrolled
Chemical and physical data
3D model (JSmol)
  • C1=C(O[H])C=CC(/C=C/C(OC2C(C(C)C)CC[C@](C)3CCCC(=C)[C@]23[H])=O)=C1
  • InChI=InChI=1S/C24H32O3/c1-16(2)20-13-15-24(4)14-5-6-17(3)22(24)23(20)27-21(26)12-9-18-7-10-19(25)11-8-18/h7-12,16,20,22-23,25H,3,5-6,13-15H2,1-2,4H3/b12-9+/t20?,22-,23?,24-/m1/s1
  • Key:IIZXOWSEQGPRRJ-ANPFOTSGSA-N

Caleicine (Caleicin) is a sesquiterpene found in Calea Ternifolia.[1] that is thought to contribute to the oneirogenic effects.

Caleicine is the p-Coumaric ester of junenol and has no lactone moiety making it distinctly unique from the other sesquiterpene lactones in Calea Ternifolia.

Chemistry

Caleicine is a sesquiterpene that has a phenylpropanoid moiety bonded to junenol[2]

In an investigation, lab mice were administered with an aqueous solution of Calea Ternifolia in doses of 200, 400 and 800mg and made to undergo a forced swim test. Under dosages of 400 and 800mg, the mice showed depressive like effects.[3]

Theorised Mechanism of action

The mechanisms of Calea Ternifolia induced Somnolence are not well understood, however, Caleicine could play a role due to its potential metabolism.

Caleicine contains p-Coumaric acid. In the body, p-Coumaric acid is biosynthesised into many lignols and phenylpropanoids including eugenol.

Eugenol biosynthesis. P-Coumaric Acid, labelled 4-Coumaric Acid, is listed at step 2

Eugenol acts as a positive allosteric modulator of the GABAA receptor which is common amongst oneirogens. In addition, eugenol inhibits both MAO-A and MAO-B, preventing the reuptake of Serotonin, Melatonin and Dopamine.[4]

Eugenol is one of many potential metabolites of Caleicine and the mechanisms of both Caleicine and Calea Ternifolia are largely misunderstood.


See also

References

  1. ^ Mata, Rachel (July 2021). "Calea ternifolia Kunth, the Mexican "dream herb", a concise review". Canadian Science Publishing: 7 – via ResearchGate.
  2. ^ PubChem. "Junenol". pubchem.ncbi.nlm.nih.gov. Retrieved 2024-11-03.
  3. ^ Sałaga, Maciej (2016). "Neuropharmacological characterization of the oneirogenic Mexican plant Calea zacatechichi aqueous extract in mice". Metabolic Brain Disease: 5 – via ResearchGate.
  4. ^ Tsuchiya, Hironori (2017). "Anesthetic Agents of Plant Origin: A Review of Phytochemicals with Anesthetic Activity". Molecules. 22 (8): 1369.