| Stereochemistry | ACHIRAL |
| Molecular Formula | C6H6N2O3 |
| Molecular Weight | 154.1234 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=C(O)C=C(C=C1)[N+]([O-])=O
InChI
InChIKey=DOPJTDJKZNWLRB-UHFFFAOYSA-N
InChI=1S/C6H6N2O3/c7-5-2-1-4(8(10)11)3-6(5)9/h1-3,9H,7H2
2-Amino-5-nitrophenol is produced from 2-aminophenol by reaction with acetic
anhydride to form 2-methylbenzoxazole, which is nitrated and hydrolysed to form 2-amino5-nitrophenol. It was first sythesized by Kaltwasser and Oehrn In 1920. 2-Amino-5-nitrophenol is used as an intermediate in the manufacture of several azo
dyes, including CI Solvent Red 8, which is used for colouring synthetic resins, lacquers, inks
and wood stains. 2-Amino-5-nitrophenol is also used in many countries as a dye in semi-permanent hair
colouring products to produce red and gold-blond shades. These products are generally
shampooed into the hair, lathered and then allowed to remain in contact with the hair and
scalp for 30-45 min. For this application, 2-amino-5-nitrophenol is mixed (at levels up to
0.5 %) with a blend of several other dyes in a shampoo base to produce the final colour or tint
desired. It has been used
(and still is to a limited extent) in permanent hair colouring products. The use of 2-amino-5-nitrophenol in cosme tic products is prohibited in the European
Economic Community.
Originator
Approval Year
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
PubMed
Patents
Sample Use Guides
Mice: Groups of 50 male and 50 female B6C3F1 mice, seven to eight weeks of age, were
administered 0, 400 or 800 mg/kg bw 2-amino-5-nitrophenol (98% pure) by gavage in corn
oil (10 ml/kg) on five days a week for up to 103 weeks and were kiled at 112 weeks of age. The mean body weights of high-dose males were 8- 11 % lower than those of vehicle controls
from week 29 to week 74, whereas those of low-dose males were greater than those of vehicle
controls throughout most of the study. The mean body weights of low-dose and high-dose
female mice were 5-9 and 8-13 % lower than those of vehicle controls from week 69 to the
end of the study, respectively. Survival of high-dose males after week 20 and of females after
week 22 was reduced compared with that of controls.
Route of Administration:
Oral
SUBSTANCE RECORD
