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Dinitolmide

HCID 3092
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
148-01-6
Standard SMILES
Cc1c(C(N)=O)cc([N+](=O)[O-])cc1[N+](=O)[O-]
InChIKey
ZEFNOZRLAWVAQF-UHFFFAOYSA-N
Molecular formula
C8H7N3O5
Average molar mass
225.16 g/mol
Monoisotopic mass
225.03857033

Overview

Yellowish, crystalline solid. Mp: 177 °C. Very slightly soluble in water. Soluble in acetone, acetonitrile, and dimethylformamide. Used as an anti-parasite drug for poultry. Store in a cool, ventilated place, away from acute fire hazards and easily oxidized materials.

Names & identifiers

Preferred name
Dinitolmide
IUPAC
2-methyl-3,5-dinitrobenzamide
English name
Dinitolmide
Molecular formula
C8H7N3O5
Molecular weight
225.16

Names & synonyms

dinitolmide2-Methyl-3,5-dinitrobenzamide148-01-6ZoaleneZoamix3,5-Dinitro-o-toluamideCoccidine ACoccidotDinitolmidaBenzamide, 2-methyl-3,5-dinitro-DinitolmidumDinitrotoluamide
Show more names
d.o.t.ZoalereNITROMIDCoccidinSalcostat
MethyldinitrobenzamideZoaleleo-Toluamide, 3,5-dinitro-DTXSID6042521AOX68RY4TVNSC-7582133,5-Dinitro-2-methylbenzamideDTXCID4022521

Database identifiers

CAS
148-01-6
PubChem CID
3092
DTXSID
DTXSID6042521
ChEMBL
CHEMBL472565
ChEBI
CHEBI:174162
UNII
AOX68RY4TV
EC Number
205-706-4
Nikkaji
J2.959I

Properties

Computed structural properties

XLogP
0.7
Topological polar surface area
135 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
5
Rotatable bonds
1
Heavy atoms
16
Formal charge
0
Complexity
321

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Other Aromatics (Nitrogen)
Color/Form · 3 items

Crystals from dilute alcohol

Yellowish, crystalline solid

Yellowish solid or needles from aqueous ethanol

Solubility · 6 items

Slight (NIOSH, 2024)

Very slightly soluble in water; soluble in acetone, acetonitrile, and dimethyl formamide

Soluble in dioxane

1 mg/mL

Solubility in water: poor

Slight

Animal DrugsFDA approved animal drugs -> Active ingredient
Melting Point · 5 items

351 °F (NIOSH, 2024)

181 °C

181 °C

181 °C

351 °F

Vapor Pressure · 2 items

0.00000007 [mmHg]

6.78X10-8 mm Hg at 25 °C /Estimated/

Henry's Law ConstantHenry's Law constant = 3.8X10-14 atm-cu m/mole @ 25 °C /Estimated/
Physical Description

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 2.3% (1 of 44) of reports.

Warning

H302 (97.7%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 44 reports by companies from 2 notifications to the ECHA C&L Inventory.

Warning

Hazard information

Regulatory InformationDinitro-o-toluamide: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - Benzamide, 2-methyl-3,5-dinitro-: Environment tier I assessment
Fire HazardsNot combustible.
Health HazardsExcerpt from NIOSH Pocket Guide for Dinitolmide:
Hazards SummaryIn animals: methemoglobinemia, liver changes; [NIOSH] May cause skin irritation and possibly liver effects; [ACGIH]
FDA Requirements · 1 item

Tolerances are established for residues of zoalene (3,5-dinitro-o- toluamide) and its metabolite 3-amino-5-nitro-o-toluamide in food as follows: (a) In edible tissues of chickens: (1) 6 parts per million in uncooked liver and kidney; (2) 3 parts per million in uncooked muscle tissue; (3) 2 parts per million in uncooked fat. (b) In edible tissues of turkeys: 3 parts per million in uncooked muscle tissue and liver.

Reactive GroupAmides and Imides

Chemistry & industry

Pharmacology

ATC CodeQP - Antiparasitic products, insecticides and repellents
MeSH Pharmacological ClassificationAgents useful in the treatment or prevention of COCCIDIOSIS in man or animals.
Cellular LocationsCytoplasm

Uses & manufacturing

Uses · 3 items

Used as a veterinary coccidiostat and food additive; [ACGIH] Coccidiostats are any of a group of chemical agents, e.g., nitrofurazone, nitrophenide, nicarbazin, mixed in feed or drinking water to control coccidiosis in animals. [Dorland's Illustrated Medical Dictionary]

For 3,5-dinitro-o-toluamide (USEPA/OPP Pesticide Code: 037510) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Medication: (Vet): Coccidiostat

Formulations/PreparationsZoalene
General Manufacturing InformationHarris et al, US 2937204 (1960 to Dow)
Applications · 5 items

DescriptionDinitolmide is a yellowish crystalline substance. Molecular weight= 225.18; Freezing/Meltingpoint = 177.2℃. Very slightly soluble in water.

UsesDinitolmide may be used as an analytical reference standard for the quantification of the analyte in animal tissues poultry, livestock, and aquatic tissues using chromatography techniques.

UsesA fodder additive for poultry used to prevent coccidiosis infections. Antiprotozoan drug.

antiprotozoal

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
· 5 items

Yellowish, crystalline solid. Mp: 177 °C. Very slightly soluble in water. Soluble in acetone, acetonitrile, and dimethylformamide. Used as an anti-parasite drug for poultry. Store in a cool, ventilated place, away from acute fire hazards and easily oxidized materials.

Yellowish, crystalline solid; [NIOSH]

Solid

YELLOW CRYSTALLINE POWDER.

Yellowish, crystalline solid.

Collision Cross Section143.7 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Other Experimental PropertiesHydroxyl radical reaction rate constant = 2.1X10-12 cu cm/molecule-sec @ 25 °C /Estimated/

Physicochemical properties

Melting point
170 · 170-180 °C (lit.)
Boiling point
366.66 °C · 366.66°C (rough estimate)
Density
1.5406 · 1.5406 (rough estimate)
refractive index
1.74 · 1.7400 (estimate)
Flash point
2 °C · 2 °C
storage temp.
2 · 2-8°C
solubility
Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
form
Solid
pka
13.74 · 13.74±0.50(Predicted)
color
Pale Beige to Light Beige
Merck
13 · 13,3297
InChI
InChI=1S/C8H7N3O5/c1-4-6(8(9)12)2-5(10(13)14)3-7(4)11(15)16/h2-3H,1H3,(H2,9,12)
InChIKey
ZEFNOZRLAWVAQF-UHFFFAOYSA-N
SMILES
C(N)(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1C
FDA 21 CFR
556.77 · 556.770; 558.4; 558.680
CAS DataBase Reference
148 · 148-01-6(CAS DataBase Reference)
NCI Dictionary of Cancer Terms
DOT
FDA UNII
68 RY4TV · AOX68RY4TV
EPA Substance Registry System
Zoalene (148-01-6)
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302
Precautionary statements
264 · P264-P270-P301+P312-P501
PPE
95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes
Xn
Risk Statements
22 · 22
Safety Statements
36 · 36
OEB
B
OEL
5 mg/m3 · TWA: 5 mg/m3
WGK Germany
2 · 2
RTECS
4200000 · XS4200000
HS Code
29242990 · 29242990
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
4 Oral · Acute Tox. 4 Oral
Hazardous Substances Data
148 · 148-01-6(Hazardous Substances Data)
Reactivity Profile
DINITOLMIDE reacts as an oxidizing agent. Has been known on at least one occasion to explode destructively. Incompatible with easily oxidized materials. Emits toxic NOx fumes if heated to decomposition.
Flammable LimitsNoncombustible Solid
Air and Water ReactionsNo rapid reaction with air. No rapid reaction with water.
NIOSH RecommendationsRecommended Exposure Limit: 10 Hr Time-Weighted Avg: 5 mg/cu m
Hazard Classes and Categories · 2 items

Acute Tox. 4 (97.7%)

Acute toxicity (Oral) - Category 4

Safety & protection

Fire FightingIn case of fire in the surroundings, use appropriate extinguishing media.
First Aid Measures · 4 items

Fresh air, rest.

Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth.

First Aid · 2 items

Excerpt from NIOSH Pocket Guide for Dinitolmide:

(General first aid procedures)

Disposal Methods · 1 item

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Spillage DisposalPersonal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting.
Preventive Measures · 5 items

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

The worker should immediately wash the skin when it becomes contaminated.

Work clothing that becomes wet or significantly contaminated should be removed and replaced.

Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.

Eye PreventionWear safety goggles.
Inhalation RiskA nuisance-causing concentration of airborne particles can be reached quickly when dispersed.
Skin PreventionProtective gloves.
Ingestion PreventionDo not eat, drink, or smoke during work.
Inhalation PreventionUse local exhaust or breathing protection.
Respirator RecommendationsImportant additional information about respirator selection

Toxicology

Target OrgansSkin, liver, blood
Ecotoxicity Values · 2 items

EC50 Daphnia magna (Water flea; intoxication, immobilization) 155 mg/L/48 hr (95% confidence interval: 146-164 mg/L); static

LC50 Daphnia magna (Water flea) 165 mg/L/48 hr (95% confidence interval: 157-173 mg/L); static

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Exposure Routes · 2 items

The substance can be absorbed into the body by ingestion.

inhalation, ingestion, skin and/or eye contact

Signs and SymptomsContact eczema; In Animals: methemoglobinemia, liver changes
ICSC Environmental DataEnvironmental effects from the substance have not been investigated adequately.
Human Toxicity Excerpts/SIGNS AND SYMPTOMS/ Potential symptom of overexposure by direct contact is eczema.
Evidence for CarcinogenicityA4; Not classifiable as a human carcinogen.
Antidote and Emergency Treatment · 2 items

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/

Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/

Non-Human Toxicity Values · 2 items

LD50 Rat oral 600 mg/kg

LD50 Dog iv 75 mg/kg

Regulatory information

FDA Requirements · 1 item

Tolerances are established for residues of zoalene (3,5-dinitro-o- toluamide) and its metabolite 3-amino-5-nitro-o-toluamide in food as follows: (a) In edible tissues of chickens: (1) 6 parts per million in uncooked liver and kidney; (2) 3 parts per million in uncooked muscle tissue; (3) 2 parts per million in uncooked fat. (b) In edible tissues of turkeys: 3 parts per million in uncooked muscle tissue and liver.

Safety data

OEB
B
OEL
TWA: 5 mg/m3
PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
2
rtecs
XS4200000
hs_code
29242990
risk_code
22
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xn
safety_code
36
Storage Class
11 - Combustible Solids
Hazard statements
H302
Hazard Classifications
Acute Tox. 4 Oral
Precautionary statements
P264-P270-P301+P312-P501
Hazardous Substances Data
148-01-6(Hazardous Substances Data)
Uses

General DescriptionYellowish, crystalline solid. Mp: 177°C. Very slightly soluble in water. Soluble in acetone, acetonitrile, and dimethylformamide. Used as an anti-parasite drug for poultry. Store in a cool, ventilated place, away from acute fire hazards and easily oxidized materials.

Upstream & downstream products

Upstream raw materials

Ammonium hydroxide3,5-Dinitro-2-methylbenzoic acidNitric acidThionyl chlorideSulfuric acid2-methyl-3,5-dinitrobenzoyl chloride

Suppliers100 total

Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
武汉欣扬瑞和化学科技有限公司13720274133 · [email protected]
湖北金梭生物科技有限公司00123456789 · [email protected]
河北创海生物科技有限公司+86-86-13131129325 · [email protected]
陕西帕尼尔生物科技有限公司029-84385017-8007 17602929471 · [email protected]
Baoji Guokang Healthchem co.,ltd+8615604608665 15604608665 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
Hebei Yanxi Chemical Co., Ltd.+86-17531190177 · [email protected]
上海弘顺生物科技有限公司15901914505 · [email protected]
北京安司莫森技术有限公司010-82954736 13391601435 · [email protected]
Syntechem Co.,Ltd[email protected]
上海晶抗生物工程有限公司021-54721350 13524668266 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
Cangzhou Wanyou New Material Technology Co.,Ltd18631714998 · [email protected]
怀化市冰峰化工有限公司0745-2866851 17711757908 · [email protected]
上海泰坦科技股份有限公司4006009262 13023226327 · [email protected]
上海隆盛化工有限公司58099637 13585536065 · [email protected]
合肥天健化工有限公司551-65418679 15856988503;15837135945 · [email protected]
云南西力生物技术股份有限公司0871-65217109 · [email protected]
天津希恩思生化科技有限公司400 638 7771 · [email protected]
Xiamen AmoyChem Co., Ltd+86-86-5926051114 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
潍坊沃腾进出口有限公司0536-2456718
武汉普洛夫生物科技有限公司17612776928 · [email protected]
南京生利德生物科技有限公司025-57798810 18652991625 · [email protected]
HBCChem, Inc.+1-510-219-6317 · [email protected]
江苏艾康生物医药研发有限公司025-66028182 17714375163 · [email protected]
武汉弘德悦欣医药科技有限公司027-83855396 15271852016 · [email protected]
上海孚一生物科技有限公司+86 (21) 61124340
凯试(上海)科技有限公司021-50135380 · [email protected]
湖北巨胜科技有限公司027-59599241 18871490274 · [email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
AN PharmaTech Co Ltd86(21)68097365 · [email protected]
桦特昇生物科技(武汉)有限公司027-59207879 1972026995 18140587686 · [email protected]
天津阿尔塔科技有限公司022-6537-8550 15522853686 · [email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
湖北威德利化学试剂有限公司18327179646 · [email protected]
厦门志信化学有限公司+86-5922680277 +86-13806087780 · [email protected]
泰安嘉岳生物化工有限公司15318151873 · [email protected]
上海珞珐生化科技有限公司021-51111890 15317326293 · [email protected]
BOC Sciences16314854226 · [email protected]
上海炎泽化工有限公司15345144255 19901447308 · [email protected]
广州市齐云生物技术有限公司020-61288194 61288195 · [email protected]
上海前衍生物科技有限公司02781293128 · [email protected]
上海西格生物科技有限公司021-57810052 18930344717 · [email protected]
南京罗迈美生物科技有限公司[email protected]

Additional notes

DefinitionChEBI: Dinitolmide is a dinitrotoluene.