Serpentine (alkaloid)

Serpentine is a terpene indole alkaloid produced by several members of the family Apocynaceae, including Catharanthus roseus[1] and Rauvolfia serpentina.[2]

Serpentine

Names
IUPAC name (19α)-16-(Methoxycarbonyl)-19-methyl-3,4,5,6,16,17-hexadehydro-18-oxayohimban-4-ium-1-ide
Other names Methyl ester of serpentinic acid
Identifiers
CAS Number	18786-24-8^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:9119
ChemSpider	65865 66108 (chloride)
ECHA InfoCard	100.038.684
PubChem CID	73391 5351483 (chloride)
UNII	B503RKE34F^Y
CompTox Dashboard (EPA)	DTXSID80927029 DTXSID40940259, DTXSID80927029
InChI InChI=1S/C21H20N2O3/c1-12-16-10-23-8-7-14-13-5-3-4-6-18(13)22-20(14)19(23)9-15(16)17(11-26-12)21(24)25-2/h3-8,11-12,15-16H,9-10H2,1-2H3/t12-,15-,16+/m0/s1 Key: WYTGDNHDOZPMIW-VBNZEHGJSA-N
SMILES C[C@H]1[C@H]2C[n+]3ccc4c5ccccc5[n-]c4c3C[C@@H]2C(=CO1)C(=O)OC
Properties
Chemical formula	C21H20N2O3
Molar mass	348.402 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

References

1. Monforte-González, M; Ayora-Talavera, T; Maldonado-Mendoza, I. E; Loyola-Vargas, V. M (1992). "Quantitative analysis of serpentine and ajmalicine in plant tissues of Catharanthus roseus and hyoscyamine and scopolamine in root tissues of Datura stramonium by thin layer chromatography-densitometry". Phytochemical Analysis. 3 (3): 117. doi:10.1002/pca.2800030305.
2. Leete, Edward (1961). "Biogenesis of the Rauwolfia alkaloids alkaloids—II". Tetrahedron. 14: 35. doi:10.1016/0040-4020(61)80084-7.