Catharanthine

Catharanthine
Names
	IUPAC name Methyl 3,4-didehydroibogamine-18-carboxylate
	Systematic IUPAC name Methyl (6R,6aR,9S)-7-ethyl-9,10,12,13-tetrahydro-5H-6,9-methanopyrido[1′,2′:1,2]azepino[4,5-b]indole-6(6aH)-carboxylate
Identifiers
CAS Number	2468-21-5;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:3469;
ChemSpider	4572197;
ECHA InfoCard	100.017.806
PubChemCID	5458190;
UNII	WT0YJV846J;
CompTox Dashboard(EPA)	DTXSID80947621;
	InChI InChI=1S/C21H24N2O2/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/h4-7,10,13,19,22H,3,8-9,11-12H2,1-2H3/t13-,19+,21-/m0/s1 Key: CMKFQVZJOWHHDV-NQZBTDCJSA-N; InChI=1/C21H24N2O2/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/h4-7,10,13,19,22H,3,8-9,11-12H2,1-2H3/t13-,19+,21-/m0/s1 Key: CMKFQVZJOWHHDV-NQZBTDCJBW;
	SMILES CCC1=C[C@H]2C[C@]3([C@@H]1N(C2)CCc4c3[nH]c5c4cccc5)C(=O)OC;
Properties
Chemical formula	C21H24N2O2
Molar mass	336.435g·mol−1
	Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa). Infobox references

Catharanthineis a terpene indole alkaloid produced by the medicinal plantCatharanthus roseusandTabernaemontana divaricata.Catharanthine is derived fromstrictosidine,but the exact mechanism by which this happens is currently unknown. Catharanthine is one of the two precursors that formvinblastine,the other beingvindoline.

Pharmacology

(+)-Catharanthine competitively inhibits α9α10nAChRswith potencies higher than that atα3β4andα4β2nAChRs and directly blocksCa_V2.2.^[1]Catharanthine alkaloids are non competitive antagonist of muscle typenAChRsand this is thought to be the case due to presence of catharanthine moiety in those compounds.^[2]Inin vitrostudy, it increased the levels ofcAMPby inhibiting cAMP phosphodiesterase in brain.^[3]It is a potent inhibitor of TRPM8, similar to BCTC.^[4]Structural analysis of catharanthine shows activity onTRPM8,TRPA1,andbutyrylcholinesterase.^[5]

References

^Arias HR, Tae HS, Micheli L, Yousuf A, Ghelardini C, Adams DJ, Di Cesare Mannelli L (September 2020). "Coronaridine congeners decrease neuropathic pain in mice and inhibit α9α10 nicotinic acetylcholine receptors and CaV2.2 channels".Neuropharmacology.175:108194.doi:10.1016/j.neuropharm.2020.108194.hdl:2158/1213504.PMID 32540451.S2CID 219705597.
^Arias HR, Feuerbach D, Targowska-Duda KM, Jozwiak K (September 2010). "Catharanthine alkaloids are noncompetitive antagonists of muscle-type nicotinic acetylcholine receptors".Neurochemistry International.57(2): 153–61.doi:10.1016/j.neuint.2010.05.007.PMID 20493225.S2CID 24594292.
^"Ethnobotany and ethnopharmacology of Tabernaemontana divaricata".
^Terada Y, Kitajima M, Taguchi F, Takayama H, Horie S, Watanabe T (August 2014). "Identification of Indole Alkaloid Structural Units Important for Stimulus-Selective TRPM8 Inhibition: SAR Study of Naturally Occurring Iboga Derivatives".Journal of Natural Products.77(8): 1831–8.doi:10.1021/np500235b.PMID 25052206.
^"Catharanthine".SwissTargetPrediction.

External links

Jadhav, A.; Liang, W.; Papageorgiou, P. C.; Shoker, A.; Kanthan, S. C.; Balsevich, J.; Levy, A. S.; Heximer, S.; Backx, P. H.; Gopalakrishnan, V. (2013). "Catharanthine dilates small mesenteric arteries and decreases heart rate and cardiac contractility by inhibition of voltage-operated calcium channels on vascular smooth muscle cells and cardiomyocytes".The Journal of Pharmacology and Experimental Therapeutics.345(3): 383–392.doi:10.1124/jpet.112.199661.PMID 23532933.S2CID 206501362.

[pmid32540451-1] Arias HR, Tae HS, Micheli L, Yousuf A, Ghelardini C, Adams DJ, Di Cesare Mannelli L (September 2020). "Coronaridine congeners decrease neuropathic pain in mice and inhibit α9α10 nicotinic acetylcholine receptors and CaV2.2 channels".Neuropharmacology.175:108194.doi:10.1016/j.neuropharm.2020.108194.hdl:2158/1213504.PMID 32540451.S2CID 219705597.

[pmid20493225-2] Arias HR, Feuerbach D, Targowska-Duda KM, Jozwiak K (September 2010). "Catharanthine alkaloids are noncompetitive antagonists of muscle-type nicotinic acetylcholine receptors".Neurochemistry International.57(2): 153–61.doi:10.1016/j.neuint.2010.05.007.PMID 20493225.S2CID 24594292.

[3] "Ethnobotany and ethnopharmacology of Tabernaemontana divaricata".

[pmid25052206-4] Terada Y, Kitajima M, Taguchi F, Takayama H, Horie S, Watanabe T (August 2014). "Identification of Indole Alkaloid Structural Units Important for Stimulus-Selective TRPM8 Inhibition: SAR Study of Naturally Occurring Iboga Derivatives".Journal of Natural Products.77(8): 1831–8.doi:10.1021/np500235b.PMID 25052206.

[5] "Catharanthine".SwissTargetPrediction.

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Pharmacology

See also

References

External links