4,6-Dinitro-o-cresol
SmallMolecule
T3DB_ID
T3D0102
描述
4,6-Dinitro-o-cresol is the most commercially important of the 18 different dinitrocresols, a class of manufactured chemicals. 4,6-Dinitro-o-cresol (DNOC) is used primarily for insect control and crop protection. It may be sold under different trade names, including Antinonnin, Detal, and Dinitrol. DNOC was used in diet pills in the 1930s, but has since been banned for this use. (L198)
类别
"Pesticide", "Pollutant", "Airborne Pollutant", "Synthetic Toxin"
同义词
"2, 4-Dinitro-o-cresol", "2,4-bis(hydroxy(oxido)amino)-6-methylphenol", "2,4-Dinitro-6-methylphenol", "2,4-Dinitro-o-cresol", "2-Methyl-4,6-dinitrophenol", "3, 5-Dinitro-2-hydroxytoluene", "3,5-Dinitro-2-hydroxytoluene", "4,6-Dinitro-2-methylphenol", "4,6-Dinitro-O-cresol", "4,6-DNOC", "6-Methyl-2,4-dinitrophenol", "Antinonin", "Antinonnin", "Arborol", "Capsine", "Degrassan", "Dekryll", "Dekrysil", "Detal", "Detol", "Dillex", "Dinitro", "Dinitro-o-cresol", "Dinitrocresol", "Dinitrodendtroxal", "Dinitrol", "Dinitromethyl cyclohexyltrienol", "Dinitrosol", "Dinoc", "Dinok", "Dinurania", "Ditrosol", "DNOC", "Effusan", "Elgetol", "Elgetol 30", "Elgetox", "Elipol", "Extrar", "Flavin-samdoz", "Hedolit", "Hedolite", "Krenite", "Kreozan", "Kresamone", "Kresonite-e", "Krezotol 50", "Lipan", "Neudorff DN 50", "Nitrador", "Nitrofan", "Prokarbol", "Rafex", "Rafex 35", "Raphatox", "Sandolin", "Selinon", "Sinox", "Trifocide", "Trifrina", "Winterwash"
CAS登记号
534-52-1
化学式
C7H6N2O5
平均分子量
198.1329
单同位素质量
198.027671312
IUPAC 名称
2-methyl-4,6-dinitrophenol
传统名称
dinitro
简化分子线性输入规范
CC1=CC(=CC(=C1O)[N+]([O-])=O)[N+]([O-])=O
InChI 标识符
InChI=1S/C7H6N2O5/c1-4-2-5(8(11)12)3-6(7(4)10)9(13)14/h2-3,10H,1H3
InChIKey=ZXVONLUNISGICL-UHFFFAOYSA-N
化合物类型
Organic compounds
大分类
Benzenoids
类型
Phenols
子类
Nitrophenols
直接大类
Dinitrophenols
另外分类
"Dinitrotoluenes", "Hydrocarbon derivatives", "Nitroaromatic compounds", "Nitrobenzenes", "Organic oxides", "Organic oxoazanium compounds", "Organonitrogen compounds", "Organooxygen compounds", "Organopnictogen compounds", "Ortho cresols", "Propargyl-type 1,3-dipolar organic compounds"
取代基
"Allyl-type 1,3-dipolar organic compound", "Aromatic homomonocyclic compound", "C-nitro compound", "Dinitrophenol", "Dinitrotoluene", "Hydrocarbon derivative", "Monocyclic benzene moiety", "Nitroaromatic compound", "Nitrobenzene", "Nitrotoluene", "O-cresol", "Organic 1,3-dipolar compound", "Organic nitro compound", "Organic nitrogen compound", "Organic oxide", "Organic oxoazanium", "Organic oxygen compound", "Organonitrogen compound", "Organooxygen compound", "Organopnictogen compound", "Propargyl-type 1,3-dipolar organic compound", "Toluene"
分子框架
Aromatic homomonocyclic compounds
外部描述符
"Nitrophenol herbicides", "dinitrophenol acaricide", "hydroxytoluene", "nitrotoluene"
地位
Detected and Not Quantified
起源
Exogenous
蜂窝位置
"Membrane"
生物流体位置
组织位置
途径
状态
Solid
外貌
Yellow solid.
熔点/沸点/溶解度
86.6°C//0.198 mg/mL at 20 °C [SCHWARZENBACH,RP et al.(1988)]
日志P
暴露途径
Oral (L198) ; inhalation (L198) ; dermal (L198)
毒性机制
4,6-Dinitro-o-cresol is an uncoupler of oxidative phosphorylation. It is believed to cause an acceleration of metabolic processes that are part of the tricarboxylic acid (TCA) cycle. DNOC produces its accelerative effect by increasing the permeability of the inner mitochondrial membrane to Ca+, altering the proton electrochemical gradient and thus interrupting the phosphate transfer to adenosine diphosphate (ADP) to form ATP. Uncoupling allows electron transport to proceed unchecked even when ATP synthesis is inhibited. As a consequence, more ADP and inorganic phosphate are available to drive the TCA cycle, and most of the energy produced from catabolism of glucose is not stored in high energy phosphate bonds as ATP but is given off as heat. This results in the elevated body temperature and related effects characteristic of DNOC toxicity. (L198)
代谢
4,6-Dinitro-o-cresol is absorbed via oral, inhalation, and dermal routes, then binds to albumin and is distributed to most tissues, including the lungs, heart, liver, kidney, brain, spleen, and muscle. Although small quantities of DNOC may be conjugated, most of it appears to be reduced to less toxic mono amino derivatives, such as 6-amino-4-nitro-o-cresol and 6-acetamido-4-nitro-o-cresol, and then subsequently conjugated. DNOC and its metabolites are eliminated primarily via the urine. (L198)
毒性值
LD50: 200 mg/kg (Dermal, Rat) (T22) LD50: 21 mg/kg (Oral, Mouse) (T22) LD50: 19 mg/kg (Intraperitoneal, Mouse) (T22) LD50: 25 600 ug/kg (Subcutaneous, Rat) (T14)
致死剂量
29 mg/kg (oral) or 1 mg/m3 (inhaled) for an adult human. (T26)
致癌性
No indication of carcinogenicity to humans (not listed by IARC).
用途/来源
4,6-Dinitro-o-cresol is used primarily for insect control and crop protection. (L198)
最低风险等级
健康影响
Exposure to DNOC may cause mild damage to the stomach, kidneys, and liver. Ingesting DNOC for long periods may cause cataracts and skin rashes. (L198)
症状
Exposure to high levels of DNOC for short periods may cause convulsions, unconsciousness, and death. Exposure to low levels of DNOC may result in an increased basal metabolic rate, increased sweating, weight loss, and increased heart rate, breathing rate, and body temperature. Other effects from DNOC exposure may include difficulty in breathing, headache, drowsiness, dizziness, and a yellowing of skin and the whites of the eyes. (L198)
治疗
药库 ID
HMDB_ID
PubChem 化合物 ID
10800
维基百科链接
创建于
2009-03-06 18:58:05 UTC
更新于
2014-12-24 20:21:06 UTC
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