Agaritine.

Molecular Structure of Agaritine (CAS NO. 2757-90-6):

IUPAC Name: (2S)-2-Amino-5-[2-[4-(hydroxymethyl)phenyl]hydrazinyl]-5-oxopentanoic acid 
Molecular Formula: C₁₂H₁₇N₃O₄
Molecular Weight: 267.281080 g/mol
XLogP3-AA: -2.8
H-Bond Donor: 5
H-Bond Acceptor: 6
Canonical SMILES: C1=CC(=CC=C1CO)NNC(=O)CCC(C(=O)O)N
Isomeric SMILES: C1=CC(=CC=C1CO)NNC(=O)CC[C@@H](C(=O)O)N
InChI: InChI=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
InChIKey: SRSPQXBFDCGXIZ-JTQLQIEISA-N
Index of Refraction: 1.638
Molar Refractivity: 69.52 cm³
Molar Volume: 193.3 cm³
Surface Tension: 70.4 dyne/cm
Density: 1.382 g/cm³
Flash Point: 248.5 °C
Enthalpy of Vaporization: 79.32 kJ/mol
Boiling Point: 487.2 °C at 760 mmHg
Vapour Pressure: 2.62E-10 mmHg at 25 °C
BRN of Agaritine (CAS NO. 2757-90-6): 0757731

  Agaritine is synthesized in three ways. The first was performed in 1962 by R.B. Kelly et al. These researchers used as their key step the coupling of the γ-azide of N-carbobenzoxy-L-glutamic acid with α- hydroxy-p-tolylhydrazine . The second way is  by reduction of p-carboxymethylphenylhydrazine with lithium aluminium hydride in situ formation, followed by a pH-neutral workup using a small quantity of saturated sodium chloride as a drying agent. This produced a mixture of compounds. Then, Agaritine was extracted by chromatography. The third way is devised in 1987 by S. Datta and L. Hoesch by joining of p-hydrazinobenzyl alcohol with the 5-carboxy group of L-glutamic acid as its keystone.

IARC Cancer Review: Group 3 IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 , 1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human No Adequate Data IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 31 , 1983,p. 63.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 31 , 1983,p. 63.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . NCI Carcinogenesis Studies (oral); No Evidence: mouse.

Mutation data reported. Questionable carcinogen. When heated to decomposition it emits toxic vapors of NO_x.

  Agaritine with cas registry number of 2757-90-6 is colorless glistening crystals, called for CCRIS 5459 ; Glutamic acid, 5-(2-(alpha-hydroxy-p-tolyl)hydrazide), L- ; HSDB 4202 ; L-Glutamic acid, 5-(2-(4-(hydroxymethyl)phenyl)hydrazide) ; L-Glutamic acid, 5-(2-(alpha-hydroxy-para-tolyl)hydrazide) ; L-Glutamic acid, 5-(2-(4-(hydroxymethyl)phenyl)hydrazide) (9CI) ; NCI-C08899 ; beta-N-(gamma-L(+)Glutamyl)4-hydroxymethylphenylhydrazine ; beta-N-(alpha-L-Glutamyl)-4-hydroxymethylphenylhydrazine . Agaritine is totally degraded after 48 hours in aqueous solution with exposure to air and oxidizes rapidly upon storage. Agaritine exists in several mushroom species such as the genera Agaricus, Leucoagaricus, and Macrolepiota. The highest amount of agaritine is found in the cap and gills of the fruiting body, and the lowest in the stem. Agaritine has been shown to induce adenomas and adenocarcinomas in the lungs of mice when administered through drinking water.