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.^[2]^[3]^[4] It exhibits cytotoxic, immunosuppressive, trypanocidal, antibacterial, as well as potent antifungal and antiluminescent activities.^[1]^[5]^[6]

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.

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References