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, structural isomer of the alkaloid strychnine. isolated from the seeds of Strychnos nux-vomica (strychnine tree). It is a secondary plant metabolite and has antitumor activity.

Isostrychnine can act as an antitumor agent because it suppresses or prevents the proliferation of tumors.^[1] Some data indicate the presence of isostrychnine in other plants of the genus Strychnos: Strychnos ignatii, Strychnos icaja and Strychnos nux-vomica.^[2]^[3]

Toxicity

Isostrychnine does not have lethal or acute toxicity.

Chemistry

It is a monoterpenoid indole alkaloid, an organic hetero hexacyclic compound, a delta-lactam, a tertiary amino compound, an olefinic compound (alkene) and a primary alcohol. It is a conjugate base of an isostrychnine(1+).^[2]^[1]

References

^ ^a ^b "isostrychnine (CHEBI:132659)". www.ebi.ac.uk. Retrieved 2025-12-13.
^ ^a ^b PubChem. "Isostrychnine". pubchem.ncbi.nlm.nih.gov. Retrieved 2025-12-13.
^ "(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". www.wikidata.org. Retrieved 2025-12-13.

[:0-1] "isostrychnine (CHEBI:132659)". www.ebi.ac.uk. Retrieved 2025-12-13.

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

[3] "(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". www.wikidata.org. Retrieved 2025-12-13.

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