catharanthine

Also known as (+)-catharanthine, methyl (2α,5β,6α,18β)-3,4-didehydro-ibogamine-18-carboxylate

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.

Chemical data

Formula: C21H24N2O2
Molecular weight: 336.4 g/mol
IUPAC name: methyl (1R,15R,18R)-17-ethyl-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4,6,8,16-pentaene-1-carboxylate
SMILES: CCC1=C[C@H]2C[C@]3([C@@H]1N(C2)CCC4=C3NC5=CC=CC=C45)C(=O)OC
InChIKey: CMKFQVZJOWHHDV-NQZBTDCJSA-N
XLogP: 2.8
Polar surface area: 45.3 Å²
H-bond donors: 1
H-bond acceptors: 3
Formal charge: 0

via PubChem

Wikidata facts

Mass: 336.183778008

Show 5 more facts

canonical SMILES: O=C(OC)C12C=3NC=4C=CC=CC4C3CCN5CC(C=C(CC)C51)C2
isomeric SMILES: CCC1=C[C@@H]2CN3CCc4c([nH]c5ccccc45)[C@@](C(=O)OC)(C2)[C@@H]13
chemical formula: C₂₁H₂₄N₂O₂
found in taxon: Tabernaemontana divaricata
Commons category: Catharanthine

Sources (2)

via Wikidata · CC0

~1 min read

Encyclopedic overview

4 sections

Contents

Pharmacology
See also
References
External links

== Pharmacology == (+)-Catharanthine competitively inhibits α9α10 nAChRs with potencies higher than that at α3β4 and α4β2 nAChRs and directly blocks CaV2.2. 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. In in vitro study, it increased the levels of cAMP by inhibiting cAMP phosphodiesterase in brain. It is a potent inhibitor of TRPM8, similar to BCTC. Structural analysis of catharanthine shows activity on TRPM8, TRPA1, and butyrylcholinesterase.

Excerpted from Wikipedia’s “catharanthine” article, available under the CC BY-SA 4.0 licence.