Conopharyngine

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]

Not to be confused with Conopharyngia elegans.
Conopharyngine
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
  • 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
C23H34N2O4
Molar mass 402.535 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

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. 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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