Serpentine (alkaloid)
{{Chembox
| Name = Serpentine
| ImageFile = serpentine structure.svg
| ImageSize = 200px
| ImageAlt =
| IUPACName = (19α)-16-(Methoxycarbonyl)-19-methyl-3,4,5,6,16,17-hexadehydro-18-oxayohimban-4-ium-1-ide
| OtherNames = Methyl ester of serpentinic acid
| Section1 = {{Chembox Identifiers
| CASNo = 18786-24-8
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII = B503RKE34F
| UNII_Ref = {{fdacite|correct|FDA}}
| PubChem = 73391
| PubChem1 = 5351483
| PubChem1_Comment = (chloride)
| ChemSpiderID = 65865
| ChemSpiderID1= 66108
| ChemSpiderID1_Comment = (chloride)
| ChEBI = 9119
| SMILES = C[C@H]1[C@H]2C[n+]3ccc4c5ccccc5[n-]c4c3C[C@@H]2C(=CO1)C(=O)OC
| StdInChI=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
| StdInChIKey=WYTGDNHDOZPMIW-VBNZEHGJSA-N
}}
| Section2 = {{Chembox Properties
| C=21|H=21|N=2|O=3
| Appearance =
| Density =
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| Section3 = {{Chembox Hazards
| MainHazards =
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Serpentine is a terpene indole alkaloid produced by several members of the family Apocynaceae (thus an "apocynaceae alkaloid"), including Catharanthus roseus{{cite journal | doi = 10.1002/pca.2800030305| title = 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| journal = Phytochemical Analysis| volume = 3| issue = 3| pages = 117| year = 1992| last1 = Monforte-González| first1 = M| last2 = Ayora-Talavera| first2 = T| last3 = Maldonado-Mendoza| first3 = I. E| last4 = Loyola-Vargas| first4 = V. M| bibcode = 1992PChAn...3..117M}} and Rauvolfia serpentina.{{Cite journal | doi = 10.1016/0040-4020(61)80084-7| title = Biogenesis of the Rauwolfia alkaloids alkaloids—II| journal = Tetrahedron| volume = 14| pages = 35–41| year = 1961| last1 = Leete| first1 = Edward| issue = 1–2}}