Securinine

Securinine
Identifiers
	IUPAC name (1S,2R,8S)-14-Oxa-7-azatetracyclo[6.6.1.01,11.02,7]pentadeca-9,11-dien-13-one;
CAS Number	5610-40-2;
PubChem CID	442872;
ChemSpider	391181;
UNII	G4VS580P5E;
KEGG	C10614;
ChEBI	CHEBI:9079;
ChEMBL	ChEMBL303062;
CompTox Dashboard (EPA)	DTXSID7045944 ;
ECHA InfoCard	100.222.962
Chemical and physical data
Formula	C13H15NO2
Molar mass	217.268 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CCN2[C@H](C1)[C@]34C[C@H]2C=CC3=CC(=O)O4;
	InChI InChI=1S/C13H15NO2/c15-12-7-9-4-5-10-8-13(9,16-12)11-3-1-2-6-14(10)11/h4-5,7,10-11H,1-3,6,8H2/t10-,11-,13+/m1/s1; Key:SWZMSZQQJRKFBP-WZRBSPASSA-N;

Securinine is an alkaloid found in Securinega suffruticosa^[1] and Phyllanthus niruri.^[2]

Pharmacology

Securinine has pro-convulsant effects^[3]^[4] and it has a strong spastic effect, similar to the actions of strychnine.^[5]

Securinine is a GABA-_A antagonist.^[6]^[7]

References

^ Du GH, Wang DS, Fang LH, Du GH (2018). "Securinine". Natural Small Molecule Drugs from Plants. Springer Singapore. pp. 325–330. doi:10.1007/978-981-10-8022-7_54. ISBN 978-981-10-8021-0.
^ Patel JR, Tripathi P, Sharma V, Chauhan NS, Dixit VK (November 2011). "Phyllanthus amarus: ethnomedicinal uses, phytochemistry and pharmacology: a review". Journal of Ethnopharmacology. 138 (2): 286–313. doi:10.1016/j.jep.2011.09.040. PMID 21982793.
^ Tao SC, Peng JZ, Lu MW (January 1986). "[Central convulsive action of l-securinine]". Zhongguo Yao Li Xue Bao = Acta Pharmacologica Sinica. 7 (1): 9–12. PMID 2876581.
^ Zhang SC, Li SZ, Gao XC, Qian LH, Yang MZ, Yuan HN, Tan DJ (July 1993). "[The adverse effects of the preparations of the active principles of Chinese herbal drugs]". Zhongguo Zhong Yao Za Zhi = Zhongguo Zhongyao Zazhi = China Journal of Chinese Materia Medica. 18 (7): 387–391. PMID 8267848.
^ Klochkov S, Neganova M (May 2021). "Unique indolizidine alkaloid securinine is a promising scaffold for the development of neuroprotective and antitumor drugs". RSC Advances. 11 (31): 19185–19195. Bibcode:2021RSCAd..1119185K. doi:10.1039/D1RA02558A. PMC 9033663. PMID 35478659.
^ "Securinine". PubChem, US National Library of Medicine. 2020-07-04.
^ Beutler JA, Karbon EW, Brubaker AN, Malik R, Curtis DR, Enna SJ (March 1985). "Securinine alkaloids: a new class of GABA receptor antagonist". Brain Research. 330 (1): 135–140. doi:10.1016/0006-8993(85)90014-9. PMID 2985189. S2CID 21138482.

[Wang-1] Du GH, Wang DS, Fang LH, Du GH (2018). "Securinine". Natural Small Molecule Drugs from Plants. Springer Singapore. pp. 325–330. doi:10.1007/978-981-10-8022-7_54. ISBN 978-981-10-8021-0.

[patel-2] Patel JR, Tripathi P, Sharma V, Chauhan NS, Dixit VK (November 2011). "Phyllanthus amarus: ethnomedicinal uses, phytochemistry and pharmacology: a review". Journal of Ethnopharmacology. 138 (2): 286–313. doi:10.1016/j.jep.2011.09.040. PMID 21982793.

[3] Tao SC, Peng JZ, Lu MW (January 1986). "[Central convulsive action of l-securinine]". Zhongguo Yao Li Xue Bao = Acta Pharmacologica Sinica. 7 (1): 9–12. PMID 2876581.

[4] Zhang SC, Li SZ, Gao XC, Qian LH, Yang MZ, Yuan HN, Tan DJ (July 1993). "[The adverse effects of the preparations of the active principles of Chinese herbal drugs]". Zhongguo Zhong Yao Za Zhi = Zhongguo Zhongyao Zazhi = China Journal of Chinese Materia Medica. 18 (7): 387–391. PMID 8267848.

[5] Klochkov S, Neganova M (May 2021). "Unique indolizidine alkaloid securinine is a promising scaffold for the development of neuroprotective and antitumor drugs". RSC Advances. 11 (31): 19185–19195. Bibcode:2021RSCAd..1119185K. doi:10.1039/D1RA02558A. PMC 9033663. PMID 35478659.

[pubchem-6] "Securinine". PubChem, US National Library of Medicine. 2020-07-04.

[7] Beutler JA, Karbon EW, Brubaker AN, Malik R, Curtis DR, Enna SJ (March 1985). "Securinine alkaloids: a new class of GABA receptor antagonist". Brain Research. 330 (1): 135–140. doi:10.1016/0006-8993(85)90014-9. PMID 2985189. S2CID 21138482.

[1]

Identifiers

IUPAC name (1S,2R,8S)-14-Oxa-7-azatetracyclo[6.6.1.0^1,11.0^2,7]pentadeca-9,11-dien-13-one
CAS Number	5610-40-2
PubChem CID	442872
ChemSpider	391181
UNII	G4VS580P5E
KEGG	C10614
ChEBI	CHEBI:9079
ChEMBL	ChEMBL303062
CompTox Dashboard (EPA)	DTXSID7045944
ECHA InfoCard	100.222.962
Chemical and physical data
Formula	C₁₃H₁₅NO₂
Molar mass	217.268 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C1CCN2[C@H](C1)[C@]34C[C@H]2C=CC3=CC(=O)O4
InChI InChI=1S/C13H15NO2/c15-12-7-9-4-5-10-8-13(9,16-12)11-3-1-2-6-14(10)11/h4-5,7,10-11H,1-3,6,8H2/t10-,11-,13+/m1/s1 Key:SWZMSZQQJRKFBP-WZRBSPASSA-N

Securinine

Pharmacology

See also

References