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N-니트로소-N-메탄올린

N-Methyl-N-nitrosoaniline

HCID 11957
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
614-00-6
표준 SMILES
CN(N=O)c1ccccc1
InChIKey
MAXCWSIJKVASQC-UHFFFAOYSA-N
분자식
C7H8N2O
평균 분자량
136.15 g/mol
단동위원소 질량
136.06366288

개요

structure

이름 및 식별자

우선 이름
N-Methyl-N-nitrosoaniline
IUPAC
N-methyl-N-phenylnitrous amide
현지명
N-니트로소-N-메탄올린
영어명
N-Nitroso-N-methylaniline
분자식
C7H8N2O
분자량
136.15

이름 및 동의어

N-Nitroso-N-methylaniline614-00-6N-Methyl-N-nitrosoanilineNitrosomethylanilinePhenylmethylnitrosamineMethylphenylnitrosamineN-Methyl-N-phenylnitrosamineN-NitrosomethylphenylamineN-METHYL-N-NITROSOBENZENAMINEAniline, N-methyl-N-nitroso-MethylnitrosoanilineBenzenamine, N-methyl-N-nitroso-
이름 더 보기
N-니트로소-N-메탄올린N-Methyl-N-phenylnitrous aMideN-nitroso-methylphenylamine or N-nitroso-N-methylaniline (NMPA)NSC 137methylphenylisoamineNitroso-N-methylaniline
N-Methyl-N-nitrosanilineMethylnitroso phenylamineN-Methyl-N-phenylnitrosoamineDTXSID90210539SM68I29WQN-nitrosomethylanilineNSC-137DTXCID801053

데이터베이스 식별자

CAS
614-00-6
PubChem CID
11957
DTXSID
DTXSID9021053
ChEMBL
CHEMBL266169
UNII
9SM68I29WQ
EC Number
210-366-5
Nikkaji
J2.998J

물성

구조 계산 물성

XLogP
1.7
극성 표면적
32.7 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
3
회전 가능 결합 수
1
무거운 원자 수
10
형식 전하
0
복잡도
110

실험 및 물리화학적 성질

Chemical ClassesNitrogen Compounds -> Nitrosamines
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
Density1.1240 g/cu cm @ 20 °C
Color/FormYELLOW CRYSTALS
SolubilityInsoluble in water; soluble in ethanol and ethyl ether
Boiling Point225 °C, decomp
DecompositionWhen heated to decomposition it emits toxic fumes of ... /nitrogen oxides/.
Melting Point14.7 °C
Vapor Pressure0.15 [mmHg]
Refractive IndexIndex of refractive = 1.5769 @ 20 °C
Physical DescriptionYellow solid; mp = 14.7 deg C; [HSDB] Liquid; [MSDSonline]
Collision Cross Section125.1 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID9021053]

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 4건

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P203, P262, P264, P264+P265, P270, P280, P301+P316, P302+P352, P305+P351+P338, P316, P318, P321, P330, P337+P317, P361+P364, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 5 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Regulatory InformationRegulation (EC) No 257/2010
Hazards Summary · 1건

Danger of cutaneous absorption; MAC-2 (considered to be carcinogenic for man because sufficient data from long-term animal studies or limited evidence from animal studies substantiated by evidence from epidemiological studies indicate that it can make a significant contribution to cancer risk); [MAK] May cause irritation; Causes liver and kidney injury in high-dose animal studies; [MSDSonline]

Clean Water Act Requirements · 2건

Toxic pollutant designated pursuant to section 307(a)(1) of the Clean Water Act and is subject to effluent limitations. /Nitrosamines/

The levels for nitrosamines through ingestion of contaminated water and contaminated aquatic organisms ... which may result in incremental increase of cancer risk over the lifetime are estimated at 1X10-5, 1X10-6, and 1X10-7. The corresponding criteria are 8.0 ng/l, 0.8 ng/l, and 0.08 ng/l, respectively. For consumption of aquatic organisms only, excluding consumption of water, the levels are 12,400 ng/l, 1,240 ng/l, and 124 ng/l, respectively. /Nitrosamines/

Hazard Classes and CategoriesAcute Tox. 3 (100%)

안전 및 보호

화학 및 산업

약리 정보

Mechanism of Action · 1건

N-Nitroso-N-methylaniline (NMA) is an esophageal carcinogen in F344 rats. Attempts to detect binding of N-nitroso-N-methylaniline to DNA or RNA have not been successful. N-nitroso-N-methylaniline is not mutagenic in the standard Ames bacterial assay, and it did not induce sister chromatid exchanges in mammalian cells. N-nitroso-N-methylaniline forms the benzenediazonium ion (BDI) during metabolism. This ion has been known to react with aromatic amines, such as adenine, to form triazene coupling products. The purpose of this research was to demonstrate that a triazene adduct, which would be expected to be hydrolytically unstable, was formed by coupling with the adenine residues in DNA. Liver DNA from a rat treated with N-nitroso-N-methylaniline or from in vitro reactions of benzenediazonium ion with DNA was treated with sodium borohydride. This reaction was shown to result in the reduction of 6-(1-phenyltriazeno)purine to 6-hydrazinopurine (N6-aminoadenine). The hydrolysate of the DNA, presumably containing the hydrazine, was treated with 4-(dimethylamino)naphthaldehyde, and the resulting hydrazone was isolated by reverse-phase HPLC using fluorescence detection. The identity of the adduct was demonstrated by high-resolution mass spectrometry. ... N-nitroso-N-methylaniline forms an unstable triazene adduct with adenine in DNA both in vitro and in vivo.

Biological Half-Life · 1건

(4.7 MG/KG, IP TO RATS) DISTRIBUTED THROUGHOUT EXTRACELLULAR WATER & CLEARED FROM WHOLE BLOOD BY METAB WITH HALF-LIFE OF 66 MIN. LESS THAN 1% OF DOSE WAS EXCRETED & EXPIRED AS PARENT CMPD. 24 HR AFTER INJECTION 46% OF 1-METHYL-(14)C WAS EXPIRED WITH HALF-LIFE OF 2.1 HR.

Metabolism/Metabolites · 6건

SODIUM PHENOBARBITAL 80 MG/KG IP INCR ACTIVITIES OF N-DEMETHYLASE OF NMA IN FEMALE & MALE RATS. FEMALES HAD HIGHER INCR THAN MALES. INCR BY METHYLCHOLANTHRENE WAS OBSERVED ONLY IN FEMALES.

HIPPURIC ACID ACCOUNTED FOR 80% OF RADIOACTIVITY FROM LABELED NMA RECOVERED IN RAT URINE.

RESULTS OF STEADY STATE KINETICS & ISOTOPE EFFECTS EXAM FOR DEMETHYLATION OF DIMETHYLNITROSAMINE & ITS DEUTERATED ANALOG USING RAT LIVER PREPARATIONS INDICATED THAT BREAKAGE OF C-H BOND IS RATE DETERMINING STEP OF THE ENZYMATIC OXIDATION.

... Reduction of nitrate to nitrite /in the gastrointestinal tract/ permits the formation of highly carcinogenic nitrosamines by reaction with secondary amines from the diet. /Nitrosamines/

관련 반응

0건
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화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트

물리화학적 성질

녹는점
13 °C · 13°C
끓는 점
128 °C · 128 °C / 19mmHg
밀도
1 · 1,13 g/cm3
굴절률
1.575 to · 1.5750 to 1.5790
인화점
13 °C · 13 °C
저장 조건
-20 °C · -20°C Freezer
수용성
물에 불용성
용해도
Chloroform: soluble; DMSO: soluble; Ethanol: soluble; Methanol: soluble
물리적 상태
투명한 액체
산도 계수 (pKa)
-1.54 · -1.54±0.50(Predicted)
색상
Light yellow to Amber to Dark green
Henry's Law Constant
2 · 2.0×100 mol/(m3Pa) at 25℃, HSDB (2015)
InChI
InChI=1S/C7H8N2O/c1-9(8-10)7-5-3-2-4-6-7/h2-6H,1H3
InChIKey
MAXCWSIJKVASQC-UHFFFAOYSA-N
SMILES
C1(N(C)N=O)=CC=CC=C1
EPA
N-Methyl-N-nitrosoaniline (614-00-6)

화학적 성질

Yellow Oil

Disposal Methods · 1건

(1) Nitrosamines may be reduced to the corresponding amine by using nickel-aluminum (Ni-Al) alloy in dilute base. The nitrosamines were completely degraded (99.9%) and only the amines (RR'NH) were found in the final reaction mixtures. No traces (generally <0.1%) of the corresponding, possibly carcinogenic, hydrazines (RR'NNH2) were found in the final reaction mixtures. (2) Nitrosamines may be oxidized by potassium permanganate in 3 M sulfuric acid (KMnO4 in H2SO4). The nitrosamines were completely destroyed (>99.5%). The products of this reaction have not been determined. (3) Nitrosamines may be destroyed by using hydrogen bromide (HBr) in glacial acetic acid. The nitrosamines were completely destroyed (>99%) and the products were presumably the corresponding amines. All of these procedures were validated by an international collaborative study. /Nitrosamines/

Personal Protective Equipment (PPE)Wear nitrile rubber gloves, protective laboratory coat, self-contained breathing apparatus, eye protection and protective shoes. /Nitrosamines/

독성 정보

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 154(SRC), determined from an estimated log Kow of 1.49(2,SRC) and a recommended regression-derived equation(3), N-methyl-N-nitrosobenzenamine is expected to have moderately high mobility in soil(SRC). Volatilization of N-methyl-N-nitrosobenzenamine from moist soil surfaces may be important(SRC) given an estimated Henry's Law constant of 4.83X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(4). N-Methyl-N-nitrosobenzenamine is not expected to volatilize from dry soil surfaces based on an estimated vapor pressure of 0.154 mm Hg(SRC), determined from a fragment constant method(5). Limited data are present in the scientific literature regarding the biodegradation of N-methyl-N-nitrosobenzenamine(SRC).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 154(SRC), determined from an estimated log Kow of 1.49(2,SRC) and a recommended regression-derived equation(3), indicates that N-methyl-N-nitrosobenzenamine is not expected to adsorb to any significant extent to suspended solids and sediment in water(SRC). N-Methyl-N-nitrosobenzenamine may volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 4.83X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Estimated volatilization half-lives for a model river and model lake are 9 and 69, respectively(3,SRC). According to a classification scheme(5), an estimated BCF of 8(3,SRC), from an estimated log Kow(2,SRC), suggests that bioconcentration in aquatic organisms is low(SRC). Limited data are present in the scientific literature regarding the biodegradation of N-methyl-N-nitrosobenzenamine(SRC). N-Methyl-N-nitrosobenzenamine may undergo hydrolysis in the environment due to the presence of hydrolyzable functional groups(3,SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), N-methyl-N-nitrosobenzenamine, which has an estimated vapor pressure of 0.154 mm Hg at 25 °C(2,SRC), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase N-methyl-N-nitrosobenzenamine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be about 1.2 days(3,SRC). Any particulate-phase N-methyl-N-nitrosobenzenamine may be physically removed from the air by wet and dry deposition(SRC). The maximum adsorption of N-methyl-N-nitrosobenzenamine, dissolved in methanol, in the UV spectrum was determined to be 270 nm, with adsorption reported up to 350 nm(4), suggesting that N-methyl-N-nitrosobenzenamine may directly photolyze since it has some adsorption above 290 nm (sunlight)(SRC).

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.
Effluent Concentrations · 1건

An N-methyl-N-nitrosobenzenamine concentration of 9 ng/ul in organic chemicals was identified in an industrial wastewater survey in which samples collected between November 1, 1979 to November 1, 1981 were analyzed for organic pollutants other than Priority Pollutants(1).

Soil Adsorption/Mobility · 1건

The Koc of N-methyl-N-nitrosobenzenamine is estimated as approximately 154(SRC), using an estimated log Kow of 1.49(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that N-methyl-N-nitrosobenzenamine is expected to have moderately high mobility in soil(SRC).

Human Toxicity Excerpts · 2건

... FETAL TISSUES ARE ESP SUSCEPTIBLE TO TRANSPLACENTAL CARCINOGENESIS, & TO SOME CMPD ... SUCH AS METHYLNITROSOANILINE ... WHICH PRODUCE PROFOUND TERATOGENIC EFFECTS AT CRITICAL PERIODS IN EMBRYOGENESIS, BUT WHICH CAUSE CARCINOGENESIS WHEN ADMIN LATER IN GESTATION.

... Health hazards ... related to the consumption of water containing large concentrations of nitrate (or nitrite) ... /include/ potential formation of carcinogenic nitrosamines. /Nitrosamines/

Artificial Pollution SourcesN-Methyl-N-nitrosobenzenamine may form at places where N-methylaniline is produced or used. (SRC)
Environmental Bioconcentration · 1건

An estimated BCF of 8 was calculated for N-methyl-N-nitrosobenzenamine(SRC), using an estimated log Kow of 1.49(1,SRC) and a recommended regression-derived equation(2). According to a classification scheme(3), this BCF suggests that bioconcentration in aquatic organisms is low.

Volatilization from Water/Soil · 1건

The Henry's Law constant for n-methyl-N-nitrosobenzeneamine is estimated as 4.83X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that N-methyl-N-nitrosobenzenamine is expected to volatilize from water surfaces(2,SRC). Based on this Henry's Law constant, the estimated volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec) is estimated as approximately 9 days(2,SRC). The estimated volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is estimated as approximately 69 days(2,SRC). N-Methyl-N-nitrosobenzenamine's Henry's Law constant(1,SRC) indicates that volatilization from moist soil surfaces may occur(SRC). N-Methyl-N-nitrosobenzenamine is not expected to volatilize from dry soil surfaces based on an estimated vapor pressure of 0.154 mm Hg(SRC), determined from a fragment constant method(3).

Non-Human Toxicity Excerpts · 5건

PRINCIPAL ORGANS AFFECTED BY CARCINOGENIC ACTIVITY OF N-NITROSO-N-METHYLANILINE IN RAT ARE ESOPHAGUS, PHARYNX & FORESTOMACH; & IN MOUSE, THE LUNGS. /FROM TABLE/

N-METHYL-N-NITROSOANILINE INCR PRECANCEROUS PROCESSES & APPEARANCE OF CANCEROUS FLAT CELLS IN ESOPHAGUS OF RATS EXPOSED TO IRRITANTS, SUCH AS TEA EXTRACTS, TOBACCO SMOKE OR ALCOHOL.

N-METHYL-N-NITROSANILINE INDUCED TUMORS IN RATS' ESOPHAGUS EPITHELIUM. AT LOW DOSES, ACANTHOSIS, HYPERKERATOSIS, PARAKERATOSIS, LEUKOPLAKIA, LEUKOKERATOSIS, PAPILLOMA, INTRAEPITHELIAL CANCER, & INVASIVE SPINAL CELLULAR CANCER WERE OBSERVED.

ACUTE & CHRONIC TOXICITIES OF N-NITROSO-N-METHYLANILINE & N-NITROSO-N-METHYLCYCLOHEXYLAMINE IN RATS OF BOTH SEXES SHOWED THAT NMA WAS A POWERFUL CONVULSANT IN RODENTS. CHRONIC ADMIN SHOWED BOTH TO BE CARCINOGENS ACTING MAINLY IN UPPER ALIMENTARY TRACT.

For more Non-Human Toxicity Excerpts (Complete) data for N-METHYL-N-NITROSOBENZENAMINE (12 total), please visit the HSDB record page.

Environmental Abiotic Degradation · 1건

The rate constant for the vapor-phase reaction of N-methyl-N-nitrosobenzenamine with photochemically-produced hydroxyl radicals has been estimated as 1.36X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 1.2 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). The maximum adsorption of N-methyl-N-nitrosobenzenamine, dissolved in methanol, in the UV spectrum was determined to be 270 nm, with adsorption reported up to 350 nm(2), suggesting that N-methyl-N-nitrosobenzenamine may directly photolyze since it has some adsorption above 290 nm (sunlight)(SRC). N-Methyl-N-nitrosobenzenamine may be expected to undergo hydrolysis in the environment due to hydrolyzable functional groups(3).

Probable Routes of Human ExposureOccupational exposure to N-methyl-N-nitrosobenzenamine may occur through inhalation of dust particles and dermal contact with this compound at workplaces where N-methylaniline is produced or used. (SRC)
Environmental Fate/Exposure Summary · 1건

N-Methyl-N-nitrosobenzenamine's presence in organic chemical effluent has been reported. If released into the atmosphere, N-methyl-N-nitrosobenzenamine will exist predominantly in the vapor phase in the ambient atmosphere, based on an estimated vapor pressure of 0.154 mm Hg at 25 °C. Vapor phase N-methyl-N-nitrosobenzenamine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals with a half-life of about 1.2 days. An estimated Koc value of 154 suggests that N-methyl-N-nitrosobenzenamine will have moderately high mobility in soil. Volatilization from moist soil may occur based upon an estimated Henry's Law constant of 4.83X10-6 atm-cu m/mole. Volatilization from dry soil surfaces should not be important given the vapor pressure of this compound. Limited data are present in the scientific literature regarding the biodegradation of N-methyl-N-nitrosobenzenamine. In water, N-methyl-N-nitrosobenzenamine should not adsorb to sediment or particulate matter based on its Koc value. This compound may volatilize from water surfaces given its estimated Henry's Law constant. Bioconcentration in aquatic organisms should be low based upon an estimated BCF value of 8. Occupational exposure may occur through inhalation of dust particles and dermal contact with this compound at workplaces where N-methylaniline is produced or used. (SRC)

규제 정보

Clean Water Act Requirements · 2건

Toxic pollutant designated pursuant to section 307(a)(1) of the Clean Water Act and is subject to effluent limitations. /Nitrosamines/

The levels for nitrosamines through ingestion of contaminated water and contaminated aquatic organisms ... which may result in incremental increase of cancer risk over the lifetime are estimated at 1X10-5, 1X10-6, and 1X10-7. The corresponding criteria are 8.0 ng/l, 0.8 ng/l, and 0.08 ng/l, respectively. For consumption of aquatic organisms only, excluding consumption of water, the levels are 12,400 ng/l, 1,240 ng/l, and 124 ng/l, respectively. /Nitrosamines/

안전 데이터

tsca
TSCA listed
rtecs
BY5775000
ridadr
2810
HS 번호
2921.44.1000
risk_code
25-36-40-22-45
hazard_code
T
safety_code
23-26-46-53-45
포장분류
III
위험 등급
6.1(b)
유해 물질 데이터
614-00-6(Hazardous Substances Data)

For more Metabolism/Metabolites (Complete) data for N-METHYL-N-NITROSOBENZENAMINE (10 total), please visit the HSDB record page.

N-nitroso-n-methylaniline (NMPhA) has known human metabolites that include N-(hydroxymethyl)-N-phenylnitrous amide.

용도 및 제조

U.S. Production · 2건

(1977) NOT PRODUCED COMMERCIALLY IN USA

(1979) NOT PRODUCED COMMERCIALLY IN USA

General Manufacturing Information · 2건

Benzenamine, N-methyl-N-nitroso-: INACTIVE

A HIGH YIELD SYNTHESIS OF (14)C-RING-LABELED & (14)C-METHYL-LABELED N-METHYL-N-NITROSOANILINE IS DESCRIBED.

상·하류 제품 정보

하류 제품

Benzenamine, N-ethyl-4-nitro-N-nitroso-

공급사94 곳

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