Agrocybin

Agrocybin
Names
	IUPAC name 8-hydroxyocta-2,4,6-triynamide
	Other names 8-Hydroxy-2,4,6-octatriynamide; 2,4,6-Octatriynamide, 8-hydroxy-
Identifiers
CAS Number	544-44-5;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1967731;
ChemSpider	10538;
PubChem CID	11004;
UNII	A0AFV4JUIT;
CompTox Dashboard (EPA)	DTXSID20202786 ;
	InChI InChI=1S/C8H5NO2/c9-8(11)6-4-2-1-3-5-7-10/h10H,7H2,(H2,9,11) Key: OXONWCQUZYDTNF-UHFFFAOYSA-N;
	SMILES C(C#CC#CC#CC(=O)N)O;
Properties
Chemical formula	C8H5NO2
Molar mass	147.133 g·mol−1
Appearance	Solid
Melting point	130–140 °C (266–284 °F; 403–413 K)
Hazards
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	6 mg/kg (IV, mice); 60 mg/kg (oral, mice)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Agrocybin is a toxic polyyne amide found in certain mushrooms, notably in the genus Agrocybe (especially Agrocybe dura) and in Marasmius oreades. It exhibits cytotoxic, immunosuppressive, trypanocidal, antibacterial, as well as potent antifungal and antiluminescent activities.

References

1 2 Yashina, O G; Vereshchagin, Leontii I (1978-03-31). "Natural and Synthetic Acetylenic Antimycotics". Russian Chemical Reviews. 47 (3): 307–317. Bibcode:1978RuCRv..47..307Y. doi:10.1070/RC1978v047n03ABEH002220. ISSN 0036-021X. Retrieved 2026-01-05.
↑ Kavanagh, Frederick; Hervey, Annette; Robbins, William J. (1950). "Antibiotic Substances from Basidiomycetes: VI. Agrocybe Dura". Proceedings of the National Academy of Sciences. 36 (2): 102–106. Bibcode:1950PNAS...36..102K. doi:10.1073/pnas.36.2.102. ISSN 0027-8424. PMC 1063141. PMID 16588952.
↑ Hearn, Milton T. W.; Jones, Ewart R. H.; Pellatt, Martin G.; Thaller, Viktor; Turner, John L. (1973). "Natural acetylenes. Part XLII. Novel C7, C8, C9, and C10 polyacetylenes from fungal cultures". Journal of the Chemical Society, Perkin Transactions 1: 2785. doi:10.1039/p19730002785. ISSN 0300-922X. Retrieved 2026-01-05.
↑ Ayer, William A.; Craw, Peter (1989-09-01). "Metabolites of the fairy ring fungus, Marasmius oreades . Part 2. Norsesquiterpenes, further sesquiterpenes, and agrocybin". Canadian Journal of Chemistry. 67 (9): 1371–1380. Bibcode:1989CaJCh..67.1371A. doi:10.1139/v89-210. ISSN 0008-4042. Retrieved 2026-01-06.
↑ Rosa, Luiz H.; Souza-Fagundes, Elaine M.; Machado, Kátia M.G.; Alves, Tânia M. A.; Martins-Filho, Olindo A.; Romanha, Alvaro J.; Oliveira, Rodrigo C.; Rosa, Carlos A.; Zani, Carlos L. (2006-05-15). "Cytotoxic, immunosuppressive and trypanocidal activities of agrocybin, a polyacetylene produced by Agrocybe perfecta (Basidiomycota)". World Journal of Microbiology and Biotechnology. 22 (6): 539–545. doi:10.1007/s11274-005-9002-7. ISSN 0959-3993. Retrieved 2026-01-05.
↑ Zheng, Yongbiao; Xu, Xiaoping; Wu, Yabin (2016). "Inhibitory activities against rice pathogens of 8-hydroxy-2,4,6-octatriynamide from Agrocybe sp". World Journal of Microbiology and Biotechnology. 32 (3) 35. doi:10.1007/s11274-015-2004-1. ISSN 0959-3993. PMID 26861586. Retrieved 2026-01-05.

[g652-1] 1 2 Yashina, O G; Vereshchagin, Leontii I (1978-03-31). "Natural and Synthetic Acetylenic Antimycotics". Russian Chemical Reviews. 47 (3): 307–317. Bibcode:1978RuCRv..47..307Y. doi:10.1070/RC1978v047n03ABEH002220. ISSN 0036-021X. Retrieved 2026-01-05.

[a062-2] Kavanagh, Frederick; Hervey, Annette; Robbins, William J. (1950). "Antibiotic Substances from Basidiomycetes: VI. Agrocybe Dura". Proceedings of the National Academy of Sciences. 36 (2): 102–106. Bibcode:1950PNAS...36..102K. doi:10.1073/pnas.36.2.102. ISSN 0027-8424. PMC 1063141. PMID 16588952.

[g715-3] Hearn, Milton T. W.; Jones, Ewart R. H.; Pellatt, Martin G.; Thaller, Viktor; Turner, John L. (1973). "Natural acetylenes. Part XLII. Novel C7, C8, C9, and C10 polyacetylenes from fungal cultures". Journal of the Chemical Society, Perkin Transactions 1: 2785. doi:10.1039/p19730002785. ISSN 0300-922X. Retrieved 2026-01-05.

[v304-4] Ayer, William A.; Craw, Peter (1989-09-01). "Metabolites of the fairy ring fungus, Marasmius oreades . Part 2. Norsesquiterpenes, further sesquiterpenes, and agrocybin". Canadian Journal of Chemistry. 67 (9): 1371–1380. Bibcode:1989CaJCh..67.1371A. doi:10.1139/v89-210. ISSN 0008-4042. Retrieved 2026-01-06.

[b087-5] Rosa, Luiz H.; Souza-Fagundes, Elaine M.; Machado, Kátia M.G.; Alves, Tânia M. A.; Martins-Filho, Olindo A.; Romanha, Alvaro J.; Oliveira, Rodrigo C.; Rosa, Carlos A.; Zani, Carlos L. (2006-05-15). "Cytotoxic, immunosuppressive and trypanocidal activities of agrocybin, a polyacetylene produced by Agrocybe perfecta (Basidiomycota)". World Journal of Microbiology and Biotechnology. 22 (6): 539–545. doi:10.1007/s11274-005-9002-7. ISSN 0959-3993. Retrieved 2026-01-05.

[n929-6] Zheng, Yongbiao; Xu, Xiaoping; Wu, Yabin (2016). "Inhibitory activities against rice pathogens of 8-hydroxy-2,4,6-octatriynamide from Agrocybe sp". World Journal of Microbiology and Biotechnology. 32 (3) 35. doi:10.1007/s11274-015-2004-1. ISSN 0959-3993. PMID 26861586. Retrieved 2026-01-05.