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1-ニトロソピロリジン

N-Nitrosopyrrolidine

HCID 13591
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
35884-45-8
標準SMILES
O=NN1CCCC1
InChIKey
WNYADZVDBIBLJJ-UHFFFAOYSA-N
分子式
C4H8N2O
平均分子量
100.12 g/mol
単同位体質量
100.06366288

概要

N-Nitrosopyrrolidine can cause cancer according to an independent committee of scientific and health experts.

名称と識別子

優先名称
N-Nitrosopyrrolidine
IUPAC
1-nitrosopyrrolidine
現地名
1-ニトロソピロリジン
英語名
N-Nitrosopyrrolidine
分子式
C4H8N2O
分子量
100.12

名称と別名

1-NitrosopyrrolidineN-NITROSOPYRROLIDINE930-55-2Pyrrolidine, 1-nitroso-NPYRNo-pyrNitrosopyrrolidineN-Nitrosopyrrolidin1-Pyrrolidinamine, N-nitroso-N-PYRDTXSID8021062Pyrrole, tetrahydro-N-nitroso-
名称をさらに表示
1-ニトロソピロリジンN-ニトロソピロリジンNニトロソピロリジン[[[N-ニトロソピロリジンN‐ニトロソピロリジンN-ニトロソピロリジン STANDARDN-ニトロソピロリジン 100ΜG/ML IN METHANOLN-ニトロソピロリジン Standard, 5.0 mg/mL in MeOHN-ニトロソピロリジン, 100 µg/mL in DichloromethaneNPY1RNPYY1NPY1-RNSC 18797
SZ4J5WK201NSC-18797Tetrahydro-N-nitroso-PyrroleDTXCID701062NSC18797N-N-PYRN NitrosopyrrolidineRefChem:389135

データベース識別子

CAS
35884-45-8、930-55-2
PubChem CID
13591
DTXSID
DTXSID8021062
ChEMBL
CHEMBL351175

物性

構造計算による物性

XLogP
-0.2
極性表面積
32.7 Ų
水素結合供与体数
0
水素結合受容体数
3
回転可能結合数
0
重原子数
7
形式電荷
0
複雑度
68.1

実験および物理化学的性質

Chemical Classes · 2 件

Nitrogen Compounds -> Nitrosamines

Carcinogens

SpringerMaterials PropertiesBoiling point
PesticidesPesticide -> EPA IRIS
LogP · 2 件

log Kow = -0.19

-0.19

Density · 3 件

1.085 at 68 °F (NTP, 1992) - Denser than water; will sink

1.085 g/cu cm at 25 °C

1.085

Color/FormYellow liquid
Solubility · 3 件

Miscible with water

Soluble in org solvents and lipids

1.00E+06 mg/L @ 24C (exp)

Flash Point · 3 件

181 °F (NTP, 1992)

181 °F

181 °F

Boiling Point · 4 件

417 °F at 760 mmHg (NTP, 1992)

214 °C

BP: 104-106 °C at 20 mm Hg

417 °F

DecompositionWhen heated to decomposition it emits toxic fumes of /oxides of nitrogen/.

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 1.6% (1 of 64) of reports.

Danger

H302 (98.4%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P318, P321, P330, P362+P364, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 64 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Not Classified

危険有害性情報

Regulatory Information · 4 件

Hazard Traits - Carcinogenicity

Regulation (EC) No 257/2010

S - indicates a substance that is identified in a final Significant New Use Rule.

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

DOT LabelPoison
Fire HazardsCombustible. (NTP, 1992)
Health HazardsACUTE/CHRONIC HAZARDS: Flammable. (NTP, 1992)
Hazards Summary · 1 件

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 injury to liver, lungs, and blood in high-dose animal studies; [MSDSonline]

Reactive GroupAzo, Diazo, Azido, Hydrazine, and Azide Compounds
Special Reports

化学と産業

薬理情報

Metabolism/Metabolites · 6 件

An excellent correlation was found between the metabolism of nitrosopyrrolidine and nitrosohexamethylenimine (probably via oxidation at the alpha-C) in rat liver microsomes and mutagenic potency in 2 bacterial mutagenic systems.

The structures of the DNA adducts formed in the metabolism of cyclic (carcinogen) N-nitrosamines are not known. The reactions with deoxyguanosine, catalyzed by porcine liver esterase, of alpha-acetoxy-N-nitrosopyrrolidine and 4-(carbethoxynitrosamino) butanal which are stable precursors to the reactive intermediates, alpha- hydroxy-N-nitrosopyrrolidine and 3-formyl-1-propanediazohydroxide, formed in the alpha-hydroxylation of the cyclic nitrosamine, N-nitrosopyrrolidine were studied. The same 2 major deoxyguanosine adducts were produced in each reaction. They were isolated by high-performance liquid chromatography and characterized by their UV spectra, mass spectra and proton magnetic resonance spectra. On the basis of these spectral data, the structures of the 2 major adducts were assigned as 3-(2-deoxy-beta-D-erythro-pentofuranosyl)-5,6,7,8-tetrahydro-8R- hydroxy-6R-methylpyrimido (1,2-a)purine-10(3H)one and 3-(2-deoxy-beta-D-erythro- pentofuranosyl)-5,6,7,8-tetrahydro-8S-h-ydroxy-6S-methylpyrimido(1,2,-a)purine- 10(3H)one, in which a new saturated 6-membered ring is formed by reaction at the 1- and N2-positions of deoxyguanosine. The same 2 adducts were formed in the reaction of crotonaldehyde (2-butenal) with deoxyguanosine. Mild acid hydrolysis of each of the 2 diastereomeric deoxyguanosine adducts yielded a pair of enantiomeric tricyclic 1,N2-guanine derivatives which had spectral properties in accordance with the assigned structures. Treatment of these tricyclic 1,N-2-guanine derivatives with sodium hydroxide and sodium borohydrate yielded N2-(3-hydroxy-1- methylpropyl) guanine, confirming the structural assignments. Unlike saturated dialkylnitrosamines which are metabolized to intermediates that give mainly 7-alkylation of deoxyguanosine, the intermediates formed in the alpha-hydroxylation of a cyclic nitrosamine, N-nitrosopyrrolidine, modify deoxyguanosine by forming cyclic 1,N2-adducts.

It is interesting to note that apparently all N,N-dialkylnitrosamines containing a tert-butyl group are noncarcinogenic. The list includes N-nitroso-1-proline, found in cured meats, particularly bacon. Although noncarcinogenic itself, nitrosoproline gives rise to the carcinogenic N-nitrosopyrrolidine during cooking. Aromatic nitrosamines are capable of transnitrosation, ie, under suitable conditions, their nitroso group can be transferred to appropriate amine-type compounds. It is thus possible that noncarcinogenic transnitrosating agents could form new carcinogenic N-nitroso compounds in the stomach.

関連反応

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化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
ChEBI
CHEBI:82362
UNII
SZ4J5WK201
EC Number
213-218-8
Nikkaji
J3.349I
Vapor Pressure · 3 件

0.06 [mmHg]

Vapor pressure determined by gas phase analysis: 0.013, 0.025, 0.13, & 0.29 mm Hg at 0, 10, 30, & 40 °C, respectively

0.06 mm Hg at 20 °C

Henry's Law ConstantHenry's Law constant = 4.89X10-8 atm-cu m/mol at 37 °C

物理化学的性質

沸点
214 °C · 214 °C(lit.)
比重(密度)
1.085 g/mL · 1.085 g/mL at 25 °C(lit.)
屈折率
20 · n20/D 1.489(lit.)
闪点
182 °F · 182 °F
貯蔵温度
2 · Sealed in dry,2-8°C
溶解性
クロロホルム(少量)、酢酸エチル、メタノール(少量)
外見
油
酸解離定数(Pka)
-3.14 · -3.14±0.20(Predicted)
色
淡い黄色から黄色
Henry's Law Constant
1.5 · 1.5×102 mol/(m3Pa) at 25℃, Klein (1982)
InChI
InChI=1S/C4H8N2O/c7-5-6-3-1-2-4-6/h1-4H2
InChIKey
WNYADZVDBIBLJJ-UHFFFAOYSA-N
SMILES
N1(N=O)CCCC1
CAS データベース
930 · 930-55-2(CAS DataBase Reference)
EPAの化学物質情報
N-Nitrosopyrrolidine (930-55-2)

化学的性質

化学的特性N-Nitrosopyrrolidine is a yellow liquid.

· 5 件

U.S. Department of Health & Human Services/National Toxicology Program; Twelfth Report on Carcinogens (2011). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. N-Nitrosopyrrolidine (930-55-2) was first listed in the Second Annual Report on Carcinogens (1981) as reasonably anticipated to be a human carcinogen.[Available from, as of August 3, 2012: http://ntp.niehs.nih.gov/]

Cottrell RC et al; Investigations of the bioactivation of N-nitrosopyrrolidine in the rat; Adv Exp Med Biol 136B (Biol React Intermed-2, Chem Mech Biol Eff, part B): 1165-71 (1982). A review of metabolism incl 3 routes of biodegradation & speclations on their relative significance in bioactivation & detoxification.

TSCA CHIPs present a preliminary assessment of N-nitrosopyrrolidine's potential for injury to human health & the environment (available at EPA's TSCA Assistance Office: (202) 554-1404

USEPA; Ambient Water Quality Criteria Doc: Nitrosamines (1980) EPA-440/5-80-064.

For more Special Reports (Complete) data for N-NITROSOPYRROLIDINE (6 total), please visit the HSDB record page.

RCRA Requirements · 1 件

U180; As stipulated in 40 CFR 261.33, when N-nitrosopyrrolidine, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

TSCA Requirements · 1 件

(a) Chemical substance and significant new use subject to reporting. (1) The chemical substance N-nitrosopyrrolidine (CAS No. 930-55-2) is subject to reporting under this section for the significant new use described in paragraph (a)(2) of this section. (2) The significant new use is: Manufacture, import, or processing of 10,000 pounds or more per year per facility for any use.

Reactivity ProfileA cyclic nitrosamine. Nitrated organics, such as N-NITROSOPYRROLIDINE, range from slight to strong oxidizing agents. If mixed with reducing agents, including hydrides, sulfides and nitrides, they may begin a vigorous reaction.
Air and Water ReactionsSoluble in water.
EPA Hazardous Waste NumberU180; A toxic waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate.

安全と保護具

Fire Fighting · 1 件

This compound is not very flammable but any fire involving this compound may produce dangerous vapors. You should evacuate the area. All firefighters should wear full-body protective clothing and use self-contained breathing apparatuses. You should extinguish any fires involving this chemical with a dry chemical, carbon dioxide, foam, or halon extinguisher. (NTP, 1992)

First Aid · 1 件

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Fire Fighting ProceduresUse dry chemical, carbon dioxide, alcohol foam, or polymer foam extinguishers.
Storage Conditions · 1 件

PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practicable to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired. ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/

Cleanup Methods · 3 件

PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms. ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal. ... The plastic bag should be sealed immediately. ... The sealed bag should be labelled properly. ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated. ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/

Decontamination of N-nitrosamine contaminated glassware /was described/. /N-Nitrosamines/

Nitrosamine residues generated in laboratory research or accidental spills in research laboratories and diluted to concn of 10 mg/L or less are rapidly reduced to innocuous amines, ammonia, or alcohols by aluminum-nickel alloy powder and aqueous alkali. The method is applicable to a variety of media (water, mineral oil, olive oil, dimethylsulfoxide, soln of agar gel) but is not recommended for use with nitrosamines in acetone or dichloromethane because reactions are slow and incomplete. After the reduced reaction mixture is filtered, the liquid is disposed of by pouring it over sufficient absorbent material to convert it to a solid waste for incineration. /Nitrosamines/

Nonfire Spill Response · 1 件

SMALL SPILLS AND LEAKAGE: You should dampen the solid spill material with acetone, then transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the adsorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a strong soap and water solution. Do not reenter the contaminate area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Disposal Methods · 5 件

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U180, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

A potential candidate for liquid injection incineration at a temperature range of 650 to 1,600 °C and a residence time of 0.1 to 2 seconds. A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids.

A one-step procedure for chemically degrading nitrosamine residues generated in research laboratory is described. Treatment with aluminum-nickel alloy powder & aqueous alkali rapidly reduced all 11 nitrosamines studied to the corresponding amines. Hydrazines were produced as transitory intermediates, but these potential carcinogens were also reduced under the conditions employed, & no products except amines, ammonia, & in some cases, alcohols were detected in the final reaction mixtures. Various solvent systems are discussed. Some of the nitrosamines degraded were NDMA, N-nitrosodiethylamine, N-nitrosodiisopropylamine, NDBA, N-nitrosomorpholine, N-nitroso-N-methylaniline, N-nitrosomethyl(methoxymethyl)amine, & N-nitroso-N,O-dimethylhydroxylamine. /Nitrosamines/

For more Disposal Methods (Complete) data for N-NITROSOPYRROLIDINE (14 total), please visit the HSDB record page.

Preventive Measures · 5 件

SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits 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. The completeness of the cleaning procedures should be considered before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at the end of shift, but should remain at employee's place of work for cleaning.

PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide additional protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/

For more Preventive Measures (Complete) data for N-NITROSOPYRROLIDINE (11 total), please visit the HSDB record page.

Isolation and EvacuationExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Personal Protective Equipment (PPE) · 3 件

MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves.

PRECAUTIONS FOR "CARCINOGENS": ... Dispensers of liq detergent ... Safety pipettes ... for all pipetting. ... In animal laboratory ... protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators ... when working with particulates or gases, & disposable plastic aprons ... gowns ... /should be/ of distinctive color. /Chemical carcinogens/

Wear nitrile rubber gloves, protective laboratory coat, self-contained breathing apparatus, eye protection and protective shoes. /Nitrosamines/

毒性情報

Cancer SitesHepatic
Interactions · 5 件

... Oral administration of ethanol (6.3 g/kg bw) 1 hr prior to administration of ... N-nitrosopyrrolidine resulted in a substantial reduction of genotoxicity that was more pronounced in the liver as compared to lungs, spleen, kidneys and blood. However, when the same ethanol dose was given 26 hr before ... N-nitrosopyrrolidine, an increase of DNA damage was found, that was, in most cases, higher in the kidneys than in the liver. Significant enhancement of genotoxic activity was also measured in lungs and spleen, whereas only a marginal increase was detectable in the blood. Repeated administration of smaller ethanol doses (2.0 g/kg body wt at 12 hr intervals) for 4 days caused a comparable increase. Similar enhancement of genotoxicity was also measured when acetone (3.5 g/kg) was given orally 15 hr before nitrosamine administration. The stimulating effect of ethanol was dose dependent and was absent when the alcohol was administered 60 hr prior to the nitrosamine. ...

N-nitrosopyrrolidine (NPYR) is an important carcinogen, frequently present in the environment and food chain. Oral administration of NPYR to experimental rats evoked severe biochemical and pathological changes. In the present investigation, the protective role of dietary fibre on NPYR-induced toxicity in hypercholesterolemic rats was studied. Supplementation of chickpea seed coat fibre in the diet reduced the hepato-toxic effects of NPYR, as evident from the decreased hepatic degeneration and improved liver weight index compared to control. Administration of NPYR resulted in an increase in the osmotic fragility of erythrocytes in the experimental animals. The antioxidant potential of experimental animals decreased in the NPYR-fed group, which was evident from the increased in vitro lipid peroxidation (LPO) of erythrocytes. However, chickpea seed coat fibre considerably reduced the peroxidative damage done by NPYR. Administration of NPYR resulted in a substantial and significant increase in LPO in all tissues, to a varying degree, though the effect was maximum in the case of the liver. Inclusion of chickpea seed coat fibre considerably reduced the peroxidative damage caused by NPYR in all tissues. The effect of NPYR administration on antioxidant potential was variable in different tissues, but the effect was reduced considerably on inclusion of chickpea seed coat fibre in the diet, providing reasonable protection against NPYR-induced oxidative stress, and, hence, its toxicity. Histopathological analysis of different tissues (heart, liver, lungs, spleen and kidneys) showed mild to severe pathological changes among the control and experimental groups. However, the pathological effects of NPYR administration were markedly reduced with the addition of chickpea seed coat fibre in the diet.

Inclusion of 10% ethanol with 6.8 ppm N-nitrosodiethylamine in the drinking water of strain A male mice resulted in a 4-fold enhancement of multiplicity of lung tumors and a 16-fold increase in incidence of forestomach tumors, compared with carcinogen alone. Given with 40 ppm N-nitrosopyrrolidine, ethanol caused a 5.5-fold increase in lung tumor multiplicity. ... The data provide additional support for the proposal that co-administered ethanol increases the tumorigenicity of nitrosamines by blocking hepatic first-pass clearance.

The effect of chronic ethanol consumption by hamsters on the carcinogenicity & target tissue metabolism of N-nitrosopyrrolidine (NPYR) was examined. Ethanol-consuming hamsters treated with NPYR developed more nasal cavity & tracheal tumors than controls. Tracheal rings isolated from ethanol-consuming hamsters metabolized NPYR at a higher rate than similar preparation from control animals.

For more Interactions (Complete) data for N-NITROSOPYRROLIDINE (14 total), please visit the HSDB record page.

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), estimated Koc values of 92 and 6(SRC), determined respectively from a structure estimation method(2) and using a log Kow of -0.19(3) and a regression-derived equation(2), indicates that N-nitrosopyrrolidine may have very high to high mobility in soil(SRC). Volatilization of N-nitrosopyrrolidine from moist soil surfaces is not expected to be an important fate process(SRC) given a measured Henry's Law constant of 4.89X10-8 atm-cu m/mole at 37 °C(4). N-Nitrosopyrrolidine is not expected to volatilize from dry soil surfaces based on a measured vapor pressure of 0.06 mm Hg at 20 °C(5). N-Nitrosopyrrolidine absorbs UV light strongly above 290 nm with a log epilson maxima of 2.2 at 335 nm(6) and a quantum yield of 0.55 in aqueous solution exposed to simulated sunlight(7); therefore, N-nitrosopyrrolidine is expected to be susceptible to direct photolysis on soil surfaces exposed to sunlight(SRC).

AQUATIC FATE: Based on a classification scheme(1), estimated Koc values of 92 and 6(SRC), determined respectively from a structure estimation method(2) and using a log Kow of -0.19(3) and a regression-derived equation(2), indicates that N-nitrosopyrrolidine is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon a Henry's Law constant of 4.89X10-8 atm-cu m/mole atm-cu m/mole(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow of -0.19(3), suggests that bioconcentration in aquatic organisms is low(SRC). The direct photolysis rate constant for N-nitrosopyrrolidine in aqueous solution exposed to irradiation representing Southern California midsummer, midday sun was observed to be 0.055/min with a half-life of 14 minutes and a quantum yield of 0.55(7). N-Nitrosopyrrolidine is stable at room temperature for more than 14 days in neutral or alkaline aqueous solutions in the dark(8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), N-nitrosopyrrolidine which has a measured vapor pressure of 0.06 mg Hg at 20 °C(2) will exist solely as a vapor in the ambient atmosphere. Vapor-phase N-nitrosopyrrolidine 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 25 hours(SRC), calculated from its rate constant of 1.55X10-11 cu cm/molecule-sec at 25 °C that was derived using a structure estimation method(3). N-Nitrosopyrrolidine absorbs UV light strongly above 290 nm with a log epilson maximum of 2.2 at 335 nm(4) and a quantum yield of 0.55 in aqueous solution exposed to simulated sunlight(5); therefore, N-nitrosopyrrolidine is expected to be susceptible to direct photolysis by sunlight(SRC).

Food Survey Values · 5 件

IIn the US, the average content in bacon is decreasing. A study in 1971-1974 showed 67 ug/kg; in 1975-76, the value was 17 ug/kg.

NPYR /N-nitrosopyrrolidine/ was found in 50% of 46 samples of several types of animal feed at levels of 1-26 ug/kg. ... Found levels of 2-8 ug/kg in 5/6 fishmeal samples.

N-Nitrosopyrrolidine has been found in a number of foods, primarily meat products(1).[Table#5166]

Dry premixed cures containing spices and sodium nitrite were found to contain up to 40 ug/kg NPYR /N-nitrosopyrrolidine/ when received; this could increase up to 520 ug/kg during 6-mo storage. ... Found 730 ug/kg NPYR in a spice-cure mixture buffered with sodium carbonate.

None of the 11 types of cheese (9 Italian, 2 Dutch) analyzed for volatile nitrosamines contained N-nitrosopyrrolidine (detection limit 1.67 ug/kg)(3). The concentration of N-nitrosopyrrolidine in 15 samples of smoked fried bacon and 10 samples of unsmoked fried bacon was <2.0 to 19.0 ug/kg and <2.0 to 9.0 ug/kg, respectively; the median concentrations were 9.0 and 4.0 ug/kg, respectively(1). Of 25 samples of cheese, meat and fish analyzed for N-nitrosopyrrolidine, levels were <0.5 ug/kg in 8 samples and ranged from 1.0 to 11.0 ug/kg in the other samples(2). The food containing 11 ug/kg was fried pig's liver. Samples of fried dry-cured bacon and drippings from 16 production plants contained mean N-nitrosopyrrolidine concentrations of 3.4 to 15.9 and 7.6 to 42.1 ppb, respectively(4). In a preliminary survey of the Italian market, the concentration of N-nitrosopyrrolidine in canned pork with jelly was 2.35 ppb; its concentrations in other luncheon meat products ranged from <0.3 to 5.88 ppb and it was not detected in cured meat products (detection limit 0.3 ppb)(5). Only two of 63 samples of various fish and seafoods analyzed for volatile nitrosamines contained N-nitrosopyrrolidine, smoked cod and smoked kippers, containing 1.9 ppb each (detection limit 0.1 to 0.2 ppb)(6). N-Nitrosopyrrolidine was detected 75 samples of fried pork bacon at a range of 0.7-25 ug/kg (mean 6.7 ug/kg)(7).

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.
Average Daily IntakeFood Intake: 0.1-0.15 ug by male person in Federal Republic of Germany(1).
Plant ConcentrationsN-Nitrosopyrrolidine was detected, not quantified in the fruit of Capsicum annuum L., also known as bell pepper, cherry pepper, cone pepper, green pepper, paprika, or sweet pepper(1).
Effluent Concentrations · 1 件

N-Nitrosopyrrolidine was found at concentrations of 0.09-0.02 ug/L in water from 2 to 19 chemical factories(1). N-Nitrosopyrrolidine concentrations of 4.2 ppb and 1.3 ppb were found in municipal sewage sludge from San Diego and Seattle, respectively(2). Analysis of anaerobic digester mixed liquor (ADML) from three wastewater treatment plants in the southeastern US detected N-nitrosopyrrolidine concentrations of <25 ng/L(3); N-nitrosopyrrolidine concentrations in the primary sludge supernatant and thickened waste-activated sludge ranged from <50 to 59 ng/L(3).

EPA IRIS Information · 2 件

N-Nitrosopyrrolidine

Hepatic

Medical Surveillance · 1 件

PRECAUTIONS FOR "CARCINOGENS": ... In relation specifically to cancer hazards, there are at present no health monitoring methods that may ensure the early detection of preneoplastic lesions or lesions which may prelude them. Whenever medical surveillance is indicated, in particular when exposure to a carcinogen has occurred, ad hoc decisions should be taken concerning additional tests that might become useful or mandatory. /Chemical Carcinogens/

Soil Adsorption/Mobility · 1 件

The Koc of N-nitrosopyrrolidine is estimated as 6(SRC), using a log Kow of -0.19(1) and a regression-derived equation(2). Using a structure estimation method based on molecular connectivity indices(2), the Koc of can be estimated to be 92(SRC). According to a classification scheme(3), these estimated Koc value suggest that N-nitrosopyrrolidine may have very high to high mobility in soil.

Natural Pollution Sources · 1 件

The most significant source of N-nitrosamines and N-nitrosamides in the environment is probably nitrosation of amine and amide precursors. These reactions may occur in air, soil, water, food and animal systems, when the precursors are present simultaneously. /N-Nitrosamines and N-Nitrosamides/

法規制情報

RCRA Requirements · 1 件

U180; As stipulated in 40 CFR 261.33, when N-nitrosopyrrolidine, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

TSCA Requirements · 1 件

(a) Chemical substance and significant new use subject to reporting. (1) The chemical substance N-nitrosopyrrolidine (CAS No. 930-55-2) is subject to reporting under this section for the significant new use described in paragraph (a)(2) of this section. (2) The significant new use is: Manufacture, import, or processing of 10,000 pounds or more per year per facility for any use.

CERCLA Reportable Quantities · 1 件

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1 lb or 0.454 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

Clean Water Act Requirements · 2 件

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

The levels for N-nitrosopyrrolidine 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 160 ng/L, 16 ng/L, and 1.6 ng/L, respectively. For consumption of aquatic organisms only, excluding consumption of water, the levels are 919,000 ng/L, 91,900 ng/L, and 9,190 ng/L, respectively. /Nitrosamines/

State Drinking Water Guidelines · 2 件

(AZ) ARIZONA 0.02 ug/l

(FL) FLORIDA 4 ug/l

安全データ

wgk
3
tsca
TSCA listed
rtecs
UY1575000
ridadr
2810
毒性
LD50 orally in rats: 900 mg/kg (Druckrey)
risk_code
40
hazard_code
Xn
hazard_class
6.1(b)
packing_group
III
Hazard Classifications
Acute Tox. 4 OralCarc. 2
ストレージクラス
10 - Combustible liquids
有毒物質データの
930-55-2(Hazardous Substances Data)

Less than 1% of ip dose of NPYR appeared as n-nitroso-3-hydroxy-pyrrolidine in urine of rats. Alkylated base, which was not identified ... was isolated from hydrolysates of liver DNA. (3)h-NPYR administration to rats reacted with DNA and RNA; however, no products were characterized.

For more Metabolism/Metabolites (Complete) data for N-NITROSOPYRROLIDINE (25 total), please visit the HSDB record page.

NPYR has known human metabolites that include 2-Pyrrolidinol, 1-nitroso-.

Absorption, Distribution and Excretion · 4 件

After ip administration of 6 mg/kg bw (2,5-(14)c)- or (3,4-(14)c)-NPYR to rats, these compounds were converted to (14)CO2 to extent of 18-25% within 6 hr; 7% of radioactivity was excreted in urine and only 1-2% in feces. Oral dose of 4 mg/kg bw (2,5-(14)c)-NPYR was converted to (14)CO2 to extent of 77%, while only 14% of dose of 650 mg/kg bw appeared as (14)CO2 in 24 hr.

Whole-body autoradiography performed with hemisections of mice at -80 °C and dry tape-sections, using pretreated and non-pretreated mice, indicated uniform distribution of non-metabolized N-nitrosopyrrolidine in tissues. At the shortest survival intervals (1 and 5 min) a high level of metabolites were found in liver, tracheo-bronchial and nasal mucosa and harder's gland which indicates local formation of metabolites in these tissues. At later survival intervals (0.5-24 hr) metabolites were in addition found in tissues with rapid cell turnover and high rate of protein synthesis and in brown fat.

... Nitrosamines ... can presumably cross the placenta since they are capable of inducing neoplasma in the offspring if administered to rats in late pregnancy. /Nitrosamines/

Differential pulsed polarography in 0.05M sulfuric acid was used for the determination of urinary concentration of nonmetabolized N-nitrosamines in rats 24-72 hr after intragastric administration of 0.01-0.5 LD50 of ... N-nitrosopyrrolidine. ... Most of the nitrosamines were recovered in urine in less than or equal to 10% of the administered amounts. ...

Cellular LocationsCytoplasm

用途と製造

Uses · 2 件

Used as a research chemical; [HSDB] Present in food products and tobacco smoke; [Merck Index]

N-Nitrosopyrrolidine is used primarily as a research chemical and is not produced commercially in the United States

U.S. Production · 3 件

(1977) NOT PRODUCED COMMERCIALLY IN USA

(1982) NOT PRODUCED COMMERCIALLY IN USA

(1978) Not produced commercially in the USA

Methods of ManufacturingThe reaction of pyrrolidine with potassium nitrate in a weak hydrochloric acid solution ... No evidence was found that NPYR has been produced commercially.
General Manufacturing InformationPyrrolidine, 1-nitroso-: ACTIVE
応用分野 · 4 件

用途実験用発ガン剤

説明N-Nitrosopyrrolidine (NPYR) is a nitrosamine compound that is used primarily as a research chemical and is not produced commercially. There is the possibility of generating NPYR after frying in dry-cured bacon. The major amine precursors to NPYR in cooked bacon are free proline in the adipose tissue and to a lesser extent, collagenous connective tissues. When proline peptides were heated with nitrite at pH 3.4, small amounts of NPYR were formed from all tested peptides. There are several potential sources of exposure of man to this group of potent carcinogens. Certain foods were thought to be derived from the interaction of nitrite with secondary amines in the food, either spontaneously or by the agency of bacteria. Recently the possibility that nitrosamines may be formed from secondary amines and nitrite in the gastrointestinal tract has been explored. The acid conditions that prevail in the human stomach favor the nitrosation of dimethylamine. In addition, at neutral pH, many secondary amines can be nitrosated by nitrite or nitrate in the presence of intestinal bacteria, or the cecal contents of the rat, and soluble enzymes which catalyze the N-nitrosation of several secondary amines have been extracted from two microorganisms. The rate of nitrosamine formation depends greatly on the basicity of the amine; the less basic amines such as diphenylamine and pyrrolidine are nitrosated far more readily than the strongly basic dimethylamine and diethylamine.

使用One of the N-nitroso compounds (NOCs) implicated in human colon carcinogenesis, but the toxicological mechanisms involved have not been elucidated.

一般的な説明Yellow liquid found in certain food products and tobacco smoke. Probably a carcinogen.

上流・下流製品情報

上流原料

Pyrrolidine-1-dPyrrolidine, 1-fluoro-(2E,4E)-1-ピロリジノ-5-(1,3-ベンゾジオキソール-5-イル)-2,4-ペンタジエン-1-オン1-ニトロピロリジン1-アセチルピロリジンN-nitrosomethyl-(2-hydroxyethyl)amine亜硝酸プロピルN-メチル-p-トルエンスルホンアミドニトロブロモメタン

下流製品

1-ホルミルピロリジンピロリジン-1-アミンピロリジン

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