{{Chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477243563 | ImageFile = Agaritine.svg | ImageFile_Ref = {{Chemboximage|correct|??}} | ImageSize = 244 | ImageName = Stereo structural formula of agaritine ((2S)-2-amino) | ImageFile1 = Agaritine_3d_structure.png | ImageFile1_Ref = {{Chemboximage|correct|??}} | ImageSize1 = 244 | ImageName1 = Ball and stick model of agaritine ((2S)-2-amino) | IUPACName = 2-[4-(Hydroxymethyl)phenyl]-glutamohydrazide | SystematicName = 2-Amino-4-<nowiki/>{''N''<nowiki>'</nowiki>-[4-(hydroxymethyl)phenyl]hydrazinecarbonyl}butanoic acid | OtherNames = β-''N''-[γ-glutamyl]-4-hydroxymethylphenylhydrazine<br /> ''N''2-(γ-glutamyl)-4-hydroxymethylphenylhydrazine |Section1={{Chembox Identifiers | Abbreviations = AGT | CASNo = 2757-90-6 | CASNo_Ref = {{cascite|correct|CAS}} | UNII_Ref = {{fdacite|correct|FDA}} | UNII = UX8Y7QVP8M | PubChem = 17688 | PubChem1 = 439517 | PubChem1_Comment = (2''S'')-2-amino | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C01550 | MeSHName = Agaritine | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 15336 | RTECS = MA1284000 | Beilstein = 757731 | PubChem2 = 439516 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 388610 | SMILES = [O-]C(=O)[C@@H]([NH3+])CCC(=O)NNc1ccc(cc1)CO | InChI = 1/C12H17N3O4/c13-10(12(18)19)5-6-11(17)15-14-9-3-1-8(7-16)2-4-9/h1-4,10,14,16H,5-7,13H2,(H,15,17)(H,18,19)/t10-/m0/s1 | InChIKey = SRSPQXBFDCGXIZ-JTQLQIEIBZ | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C12H17N3O4/c13-10(12(18)19)5-6-11(17)15-14-9-3-1-8(7-16)2-4-9/h1-4,10,14,16H,5-7,13H2,(H,15,17)(H,18,19)/t10-/m0/s1 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = SRSPQXBFDCGXIZ-JTQLQIEISA-N }} |Section2={{Chembox Properties | C=12 | H=17 | N=3 | O=4 | MeltingPtC = 203 | pKa = 3.4 }} |Section7={{Chembox Hazards | MainHazards = Toxic }} }} '''Agaritine''' is an aromatic hydrazine-derivative mycotoxin in mushroom species of the genus ''Agaricus''.<ref name=pubchem>{{cite web|title=Agaritine|publisher=PubChem, US National Library of Medicine|url=https://pubchem.ncbi.nlm.nih.gov/compound/439517|date=24 July 2021|accessdate=27 July 2021}}</ref> It is an α-aminoacid and a derivative of phenylhydrazine.
==Occurrence== Agaritine is present as a natural mycotoxin in fresh samples of at least 24 species of the genera ''Agaricus'', ''Leucoagaricus'', and ''Macrolepiota''.<ref name=AgaratineContent>{{cite journal |doi=10.1080/02652030802039903 |title=Agaritine content of 53 ''Agaricus'' species collected from nature |year=2009 |last1=Schulzová |first1=V. |last2=Hajslova |first2=J. |last3=Peroutka |first3=R. |last4=Hlavasek |first4=J. |last5=Gry |first5=J. |last6=Andersson |first6=H.C. |journal=Food Additives & Contaminants: Part A |volume=26 |issue=1 |pages=82–93 |pmid=19680875|s2cid=427230 |url=https://hal.archives-ouvertes.fr/hal-00577390/file/PEER_stage2_10.1080%252F02652030802039903.pdf }}</ref> Mushrooms of these species are found around the world.<ref name=CompleteBookOfMushrooms>{{cite book |last1=Rinaldi |first1=Augusto |last2=Tyndalo |first2=Vassili |last3=Maggiora |first3=Laura Rosano |title=The complete book of mushrooms : over 1,000 species and varieties of American, European, and Asiatic mushrooms |publisher=Crown Publishers |year=1974 |isbn=978-0-517-51493-1}}{{page needed|date=December 2013}}</ref> These mushrooms grow in a wide range of habitats. ''Agaricus bisporus'' is cultivated in over 70 countries and on every continent except Antarctica. ''A. bisporus'', also known as the portobello or common button mushroom, is of particular socio-economic importance in developed countries.<ref name=BioCultivationMushrooms>{{cite book |last1=Hayes |first1=W. A. |last2=Chang |first2=S. T. |title=The Biology and cultivation of edible mushrooms |publisher=Academic Press |year=1978 |isbn=978-0-12-168050-3 |url=http://www.sciencedirect.com/science/book/9780121680503}}{{page needed|date=December 2013}}</ref>
Agaritine content varies between individual mushrooms and across species. Agaritine content (% fresh weight) in raw ''Agaricus bisporus'', for example, ranges from 0.033% to 0.173%, with an average of 0.088%. The highest amount of agaritine is found in the cap and gills of the fruiting body, and the lowest in the stem.<ref name=AgaratineContent /> Agaratine decomposes significantly between harvest and sale, and it has also been shown to decompose readily upon cooking (up to 90% reduction) as well as upon freezing (up to 75% reduction).<ref name=LiuJFS>{{cite journal |doi=10.1111/j.1365-2621.1982.tb04978.x |title=Agaritine Content of Fresh and Processed Mushrooms [''Agaricus bisporus'' (Lange) Imbach] |year=1982 |last1=Liu |first1=J.-W. |last2=Beelman |first2=R. B. |last3=Lineback |first3=D. R. |last4=Speroni |first4=J. J. |journal=Journal of Food Science |volume=47 |issue=5 |pages=1542–4}}</ref><ref name=RossFCT>{{cite journal |doi=10.1016/S0015-6264(82)80226-5 |title=Occurrence, stability and decomposition of ''β''-''n''[''γ''-l( + )-glutamyl]-4-hydroxymethylphenylhydrazine (agaritine) from the mushroom ''Agaricus bisporus'' |year=1982 |last1=Ross |first1=A.E. |last2=Nagel |first2=D.L. |last3=Toth |first3=B. |journal=Food and Chemical Toxicology |volume=20 |issue=6 |pages=903–7 |pmid=6131022}}</ref><ref name=SchulzovaFAC>{{cite journal |doi=10.1080/02652030210156340 |title=Influence of storage and household processing on the agaritine content of the cultivated Agaricus mushroom |year=2002 |last1=Schulzová |first1=V. |last2=Hajslová |first2=J. |last3=Peroutka |first3=R. |last4=Gry |first4=J. |last5=Andersson |first5=H. C. |journal=Food Additives and Contaminants |volume=19 |issue=9 |pages=853–62 |pmid=12396396|s2cid=23953741}}</ref>
== Production == Agaritine occurs naturally in mushrooms and can be extracted from cultivated ''Agaricus bisporus'' mushrooms with water or methanol.<ref name=pubchem/> <!-- Deleted image removed: File:agaritinebiosynth.gif
'''Figure 2'''. Proposed biosynthesis of agaritine.<ref name=twenty /> -->
Total industrial syntheses of agaritine have been completed, with an 83% yield, and the overall yield of 33%.<ref name=twentyfive>{{cite journal |doi=10.1002/hlca.19870700505 |title=Novel Synthesis of Agaritine, a 4-Hydrazinobenzyl-Alcohol Derivative Occurring in Agaricaceae |year=1987 |last1=Datta |first1=Subir |last2=Hoesch |first2=Lienhard |journal=Helvetica Chimica Acta |volume=70 |issue=5 |pages=1261–7}}</ref>
==Potential for toxicity== Although recognized as an experimental carcinogen when used in high laboratory doses, there is inadequate evidence to classify Agaritine as carcinogenic to humans in amounts ingested from consuming mushrooms.<ref name=pubchem/>
== See also == *Agaritine gamma-glutamyltransferase *Gyromitrin
== References == {{Reflist|2}}
{{Hydrazines}}
Category:Mycotoxins Category:Hydrazides Category:Hydroxymethyl compounds Category:Alpha-Amino acids Category:Amino acid derivatives