Conopharyngine

Last updated
Conopharyngine
Conopharyngine.svg
Names
IUPAC name
Methyl (1S,15S,17S,18S)-17-ethyl-6,7-dimethoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4,6,8-tetraene-1-carboxylate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
  • InChI=1S/C23H30N2O4/c1-5-14-8-13-11-23(22(26)29-4)20-15(6-7-25(12-13)21(14)23)16-9-18(27-2)19(28-3)10-17(16)24-20/h9-10,13-14,21,24H,5-8,11-12H2,1-4H3/t13-,14-,21-,23+/m0/s1
    Key: DUFLXLVGASPEMV-BPYGGHBPSA-N
  • CCC1CC2CC3(C1N(C2)CCC4=C3NC5=CC(=C(C=C45)OC)OC)C(=O)OC
Properties
C23H30N2O4
Molar mass 398.503 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Conopharyngine is the major alkaloid present in the leaves and stem-bark of Tabernaemontana pachysiphon and Conopharyngia durissima . [1] [2] [3] It is closely related voacangine and coronaridine. Conopharyngine pseudoindoxyl, a derivative of it, is also found in the same plant Tabernaemontana pachysiphon. [4]

Contents

Pharmacology

It possess central nervous system stimulant activity and produces bradycardia and hypotension in cats. It has weak acetylcholinesterase inhibitory activity and significantly increases hexobarbitone induced sleeping time. [5]

Toxicity

It has low intravenous toxicity in mice (LD50 = 143 mg/kg). [5]

See also

References

  1. ↑ "Tabernaemontana pachysiphon".
  2. ↑ van Beek TA, de Smidt C, Verpoorte R (1985). "Phytochemical investigation of Tabernaemontana crassa". Journal of Ethnopharmacology . 14 (2–3): 315–8. doi:10.1016/0378-8741(85)90096-0. PMID   4094474.
  3. ↑ Renner, U.; Prins, D. A.; Stoll, W. G. (1959). "Alkaloide ausConopharyngia durissima STAPF Isovoacangin, Conopharyngin, Conodurin und Conoduramin". Helvetica Chimica Acta. 42 (5): 1572–1581. doi:10.1002/hlca.19590420519. ISSN   0018-019X.
  4. ↑ Crooks PA, Robinson B (October 1973). "Conopharyngine pseudoindoxyl, a new alkaloid from Tabernamontana pachysiphon Stapf. var cumminsii (Stapf.) H. Huber". The Journal of Pharmacy and Pharmacology . 25 (10): 820–3. doi:10.1111/j.2042-7158.1973.tb09948.x. PMID   4149744. S2CID   9261649.
  5. 1 2 Carroll PR, Starmer GA (May 1967). "Studies on the pharmacology of conopharyngine, an indole alkaloid of the voacanga series". British Journal of Pharmacology and Chemotherapy . 30 (1): 173–85. doi:10.1111/j.1476-5381.1967.tb02123.x. PMC   1557242 . PMID   6039971.
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