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'''Caleicine''' ('''Caleicin''') is a [[sesquiterpene]] found in [[Calea ternifolia|Calea Ternifolia]].<ref>{{Cite journal |last=Mata |first=Rachel |date=July 2021 |title=Calea ternifolia Kunth, the Mexican “dream herb”, a concise review |url=https://www.researchgate.net/publication/353506934_Calea_ternifolia_Kunth_the_Mexican_dream_herb_a_concise_review |journal=Canadian Science Publishing |pages=7 |via=ResearchGate}}</ref> that is thought to contribute to the [[Oneirogen|oneirogenic]] effects.
'''Caleicine''' ('''Caleicin''') is a [[sesquiterpene]] found in [[Calea ternifolia|Calea Ternifolia]]<ref>{{Cite journal |last=Mata |first=Rachel |date=July 2021 |title=Calea ternifolia Kunth, the Mexican “dream herb”, a concise review |url=https://www.researchgate.net/publication/353506934_Calea_ternifolia_Kunth_the_Mexican_dream_herb_a_concise_review |journal=Canadian Science Publishing |pages=7 |via=ResearchGate}}</ref> that is thought to contribute to the [[Oneirogen|oneirogenic]] effects.


Caleicine is the [[P-Coumaric acid|''p''-Coumaric]] ester of junenol and has no [[lactone]] moiety making it distinctly unique from the other [[Sesquiterpene lactone|sesquiterpene lactones]] in [[Calea ternifolia|Calea Ternifolia]].
Caleicine is the [[P-Coumaric acid|''p''-Coumaric]] ester of junenol and has no [[lactone]] moiety making it distinctly unique from the other [[Sesquiterpene lactone|sesquiterpene lactones]] in [[Calea ternifolia|Calea Ternifolia]].

Revision as of 10:52, 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.