Isostrychnine

Isostrychnine
Names
	IUPAC name (1R,13S,14E,19S,21S)-14-(2-Hydroxyethylidene)-8,16-diazahexacyclo[11.5.2.11,8.02,7.016,19.012,21]henicosa-2,4,6,11-tetraen-9-one
Identifiers
CAS Number	467-16-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:132659 ;
ChEMBL	ChEMBL2164628;
ChemSpider	9199295 ;
KEGG	C22928 ;
PubChem CID	11024113;
	InChI InChI=1S/C21H22N2O2/c24-10-7-13-12-22-9-8-21-16-3-1-2-4-17(16)23-19(25)6-5-14(20(21)23)15(13)11-18(21)22/h1-5,7,15,18,20,24H,6,8-12H2/b13-7-/t15-,18-,20-,21+/m0/s1 Key: PNYOGGAOQVIZDM-JQNVFVSUSA-N ;
	SMILES С1CN2C/C(=C/CO)/[C@@H]3C[C@H]2[C@@]14[C@@H]5C3=CCC(=O)N5C6=CC=CC=C46;
Properties
Chemical formula	C21H22N2O2
Molar mass	334.419 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

Isostrychnine is a monoterpenoid indole alkaloid and a structural isomer of strychnine. It is a secondary plant metabolite and may have antitumor activity.

Occurrence

Isostrychnine has been isolated from plant extracts of Strychnos species (e.g the seeds of Strychnos nux-vomica (strychnine tree) or the roots of Strychnos icaja).^[1]^[2] It is also present in Strychnos ignatii.^[2]

Pharmacology

One study observed inhibitory effects against Hep G2 cell proliferation.^[3] Another study found isostrychnine arrested the growth of the human hepatocarcinoma cell line SMMC 7721.^[4]

References

^ Frédérich, Michel; Pauw, Marie-Claire De; Llabrès, Gabriel; Tits, Monique; Hayette, Marie-Pierre; Brandt, Viviane; Penelle, Jacques; Mol, Patrick De; Angenot, Luc (2000). "New Antimalarial and Cytotoxic Sungucine Derivatives from Strychnos icaja Roots". Planta Medica. 66 (03): 262–269. doi:10.1055/s-2000-8559. ISSN 0032-0943.
^ ^a ^b PubChem. "Isostrychnine". pubchem.ncbi.nlm.nih.gov. Retrieved 2025-12-13.
^ Deng, Xu-Kun; Yin, Wu; Li, Wei-Dong; Yin, Fang-Zhou; Lu, Xiao-Yu; Zhang, Xiao-Chun; Hua, Zi-Chun; Cai, Bao-Chang (2006-06-30). "The anti-tumor effects of alkaloids from the seeds of Strychnos nux-vomica on HepG2 cells and its possible mechanism". Journal of Ethnopharmacology. 106 (2): 179–186. doi:10.1016/j.jep.2005.12.021. ISSN 0378-8741.
^ Yin, Wu; Deng, Xu-Kun; Yin, Fang-Zhou; Zhang, Xiao-Chun; Cai, Bao-Chang (2007-09-01). "The cytotoxicity induced by brucine from the seed of Strychnos nux-vomica proceeds via apoptosis and is mediated by cyclooxygenase 2 and caspase 3 in SMMC 7221 cells". Food and Chemical Toxicology. 45 (9): 1700–1708. doi:10.1016/j.fct.2007.03.004. ISSN 0278-6915.

[1] Frédérich, Michel; Pauw, Marie-Claire De; Llabrès, Gabriel; Tits, Monique; Hayette, Marie-Pierre; Brandt, Viviane; Penelle, Jacques; Mol, Patrick De; Angenot, Luc (2000). "New Antimalarial and Cytotoxic Sungucine Derivatives from Strychnos icaja Roots". Planta Medica. 66 (03): 262–269. doi:10.1055/s-2000-8559. ISSN 0032-0943.

[:1-2] PubChem. "Isostrychnine". pubchem.ncbi.nlm.nih.gov. Retrieved 2025-12-13.

[3] Deng, Xu-Kun; Yin, Wu; Li, Wei-Dong; Yin, Fang-Zhou; Lu, Xiao-Yu; Zhang, Xiao-Chun; Hua, Zi-Chun; Cai, Bao-Chang (2006-06-30). "The anti-tumor effects of alkaloids from the seeds of Strychnos nux-vomica on HepG2 cells and its possible mechanism". Journal of Ethnopharmacology. 106 (2): 179–186. doi:10.1016/j.jep.2005.12.021. ISSN 0378-8741.

[4] Yin, Wu; Deng, Xu-Kun; Yin, Fang-Zhou; Zhang, Xiao-Chun; Cai, Bao-Chang (2007-09-01). "The cytotoxicity induced by brucine from the seed of Strychnos nux-vomica proceeds via apoptosis and is mediated by cyclooxygenase 2 and caspase 3 in SMMC 7221 cells". Food and Chemical Toxicology. 45 (9): 1700–1708. doi:10.1016/j.fct.2007.03.004. ISSN 0278-6915.

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