agaritine
{{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-
| OtherNames = β-N-[γ-glutamyl]-4-hydroxymethylphenylhydrazine
N2-(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 = (2S)-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.{{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}} 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.{{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 }} Mushrooms of these species are found around the world.{{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}} 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 common button mushroom, is of particular socio-economic importance in developed countries.{{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}}
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. 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).{{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}}{{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}}{{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}}
Production
Agaritine occurs naturally in mushrooms and can be extracted from cultivated Agaricus bisporus mushrooms with water or methanol.
Total industrial syntheses of agaritine have been completed, with an 83% yield, and the overall yield of 33%.{{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}}
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.