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  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:3469
ChemSpider	4572197
ECHA InfoCard	100.017.806
PubChem CID	5458190
UNII	WT0YJV846J  Y
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	336.435 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Catharanthine is a terpene indole alkaloid produced by the medicinal plant Catharanthus roseus and Tabernaemontana divaricata . Catharanthine is derived from strictosidine, but the exact mechanism by which this happens is currently unknown. Catharanthine is one of the two precursors that form vinblastine, the other being vindoline.

Pharmacology

(+)-Catharanthine competitively inhibits α9α10 nAChRs with potencies higher than that at α3β4 and α4β2 nAChRs and directly blocks Ca_V2.2. ^[1] Catharanthine alkaloids are non competitive antagonist of muscle type nAChRs and this is thought to be the case due to presence of catharanthine moiety in those compounds. ^[2] In in vitro study, it increased the levels of cAMP by inhibiting cAMP phosphodiesterase in brain. ^[3] It is a potent inhibitor of TRPM8, similar to BCTC. ^[4] Structural analysis of catharanthine shows activity on TRPM8, TRPA1, and butyrylcholinesterase. ^[5]

See also

• Akuammicine
• Conopharyngine
• Stemmadenine
• Tabersonine
• Dimerization of catharanthine and vindoline
• Catharanthalog

References

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.
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".
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.

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.