2-Naphthylamine

143.19

143.19

202-080-4

CKR7XL41N4

0610

1650

DTXSID2020921

C44311

COLORLESS CRYSTALS WHICH DARKEN IN AIR TO A REDDISH-PURPLE COLOR|White to red crystalls [Note: Darkens in air to reddish-purple color].

2921450010

26

2.28

pink to purple powder

1.061 g/cm³ @ Temp: 98 °C

111-113 °C

306 °C

315°F

1.694

H2O: <0.1 g/100 mL at 22 ºC;soluble in hot water, ethanol, ether

-20°C Freezer

2.56 x 10 -4 mmHg at 20–30 °C (quoted, Mercer et al., 1990)

Relative vapour density (air = 1): 4.95

Oral-Rat  LD50: 727 mg/kg; Abdominal cavity-mouse LD50: 200 mg/kg

Open flame is flammable; heat releases toxic nitrogen oxide gas

Nonexplosive

Faint aromatic odor

WEAK BASE

8.10e-08 atm-m3/mole|Henry's Law constant = 8.10X10-8 atm-cu m/mol @ 25 °C

pKa = 4.16

Reduces warm ammoniacal silver nitrate|Hydroxyl radical reaction rate constant = 2.0X10-10 cu cm/molecule-sec @ 25 °C /Estimated/

This chemical darkens in air to a reddish-purple color (oxidizes). Slightly soluble in hot water and denser than water. Napthyl amines can be slowly hydrolyzed, releasing NH3 as a byproduct [N.L. Drake, Org. React. 1, (1942), 105].

Amines, Aromatic

BETA-NAPHTHYLAMINE is a weak base. It is incompatible with strong oxidizing agents and strong acids. It is also incompatible with nitrous acid. It reduces warm ammoniacal silver nitrate. (NTP, 1992)

9.71 eV

Combustible Solid

Dust explosion possible if in powder or granular form, mixed with air.

NOT CORROSIVE

II

6.1(a)

UN 1650 6.1/PG 2

3

45-22-51/53

53-45-61

QM2100000

T,N

Storehouse ventilated at low temperature and dry; stored separately from acids, oxidants, food additives

Stable. Incompatible with strong oxidizing agents.

P201-P273-P301 + P312 + P330-P308 + P313-P391-P501

H302-H350-H411

[40 CFR 240-280, 300-306, 702-799 (7/1/2004)] Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U168, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.|A) Dissolve in such combustible solvent as alcohols, benzene, etc. Spray the soln into a furnace with afterburner and scrubber. B) Pour into a mixture of sand and soda ash (9:1). After mixing, put into a paper carton stuffed full with packing paper to serve as fuel. Burn in a furnace. Recommendable method: Incineration.|PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/|For more Disposal Methods (Complete) data for 2-NAPHTHYLAMINE (8 total), please visit the HSDB record page.

National Toxicology Program. Eleventh Report on Carcinogens (2005). 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. 2-Naphthylamine (91-59-8) is listed as known to be a human carcinogen.[Available from, as of July 31, 2009: http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s117naph.pdf]

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. (ERG, 2016)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.

|Danger|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P264, P270, P273, P281, P301+P312, P308+P313, P330, P391, P405, and P501|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|Aggregated GHS information provided by 98 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H341: Suspected of causing genetic defects [Warning Germ cell mutagenicity]|P201, P202, P281, P308+P313, P405, and P501

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)

Skin: Wear appropriate personal protective clothing to prevent skin contact. Eyes: Wear appropriate eye protection to prevent eye contact. Wash skin: The worker should immediately wash the skin when it becomes contaminated. The worker should wash daily at the end of each work shift. Remove: Work clothing that becomes wet or significantly contaminated should be removed and replaced. Change: Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premise. Provide: Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection. Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.] (NIOSH, 2016)|If there is pressing need to handle this substance, the worker should be fully protected with impervious clothing and air supplied breathing equipment. Also hands, feet and eyes should be covered. No exposure by any route should be permitted.|Respirator Selection: Fullface, supplied air respirators of continuous flow or pressure demand type should be used.|Wear appropriate personal protective clothing to prevent skin contact.|Wear appropriate eye protection to prevent eye contact.|For more Personal Protective Equipment (PPE) (Complete) data for 2-NAPHTHYLAMINE (9 total), please visit the HSDB record page.|(See protection codes)

It is combustible and at elevated temperatures evolves a vapor which is flammable ... Fire hazard: moderate, when exposed to heat or flame.

Nonexplosive

If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use foam, dry chemical, or carbon dioxide. Keep run-off water out of sewers and water sources.|/Use:/ Dry powder, foam, water spray.

Sweep spilled substance into covered containers. Carefully collect remainder, then remove to safe place. Do NOT let this chemical enter the environment.|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/

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.|The worker should wash daily at the end of each work shift.|For more Preventive Measures (Complete) data for 2-NAPHTHYLAMINE (17 total), please visit the HSDB record page.

/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Health: TOXIC; inhalation, ingestion, or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. /beta-Naphthylamine; beta-Naphthylamine, solid; beta-Naphthylamine, solution; Naphthylamine (beta); Naphthylamine (beta), solid; Naphthylamine (beta), solution/|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors, and sewers explosion hazards. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. /beta-Naphthylamine; beta-Naphthylamine, solid; beta-Naphthylamine, solution; Naphthylamine (beta); Naphthylamine (beta), solid; Naphthylamine (beta), solution/|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas. /beta-Naphthylamine; beta-Naphthylamine, solid; beta-Naphthylamine, solution; Naphthylamine (beta); Naphthylamine (beta), solid; Naphthylamine (beta), solution/|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /beta-Naphthylamine; beta-Naphthylamine, solid; beta-Naphthylamine, solution; Naphthylamine (beta); Naphthylamine (beta), solid; Naphthylamine (beta), solution/|For more DOT Emergency Guidelines (Complete) data for 2-NAPHTHYLAMINE (8 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.|PRECAUTIONS FOR "CARCINOGENS": Procurement ... of unduly large amt ... should be avoided. To avoid spilling, carcinogens should be transported in securely sealed glass bottles or ampoules, which should themselves be placed inside strong screw-cap or snap-top container that will not open when dropped & will resist attack from the carcinogen. Both bottle & the outside container should be appropriately labelled. ... National post offices, railway companies, road haulage companies & airlines have regulations governing transport of hazardous materials. These authorities should be consulted before ... material is shipped. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": When no regulations exist, the following procedure must be adopted. The carcinogen should be enclosed in a securely sealed, watertight container (primary container), which should be enclosed in a second, unbreakable, leakproof container that will withstand chem attack from the carcinogen (secondary container). The space between primary & secondary container should be filled with absorbent material, which would withstand chem attack from the carcinogen & is sufficient to absorb the entire contents of the primary container in the event of breakage or leakage. Each secondary container should then be enclosed in a strong outer box. The space between the secondary container & the outer box should be filled with an appropriate quantity of shock-absorbent material. Sender should use fastest & most secure form of transport & notify recipient of its departure. If parcel is not received when expected, carrier should be informed so that immediate effort can be made to find it. Traffic schedules should be consulted to avoid ... arrival on weekend or holiday ... /Chemical Carcinogens/

B-Naphthylamine is mildly irritating to the skin and has produced contact dermatitis.

Workers' exposure to beta-naphthylamine is to be controlled through the required use of engineering controls, work practices, & personal protective equipment, incl respirators. Identified as an occupational carcinogen without establishing a PEL.

NIOSH considers beta-naphthylamine to be a potential occupational carcinogen. NIOSH usually recommends that occupational exposures to carcinogens be limited to the lowest feasible concentration.

Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Sweep spilled substance into sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

Separated from food and feedstuffs. Well closed. Store in an area without drain or sewer access.

Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed.

The substance may be irritating to the respiratory tract and skin. The substance may cause effects on the blood. This may result in the formation of methaemoglobin. The substance may cause effects on the bladder. This may result in inflammation and blood in the urine. Medical observation is indicated. The effects may be delayed.

This substance is carcinogenic to humans.

NO open flames. PREVENT DISPERSION OF DUST.

AVOID ALL CONTACT! IN ALL CASES CONSULT A DOCTOR!

Use closed system or ventilation.

Protective gloves. Protective clothing.

Wear face shield or eye protection in combination with breathing protection if powder.

U168; A toxic waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or manufacturing chemical intermediate.

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; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

U168; As stipulated in 40 CFR 261.33, when beta-naphthylamine, 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).

2-Naphthylamine was detected in aqueous industrial effluent extracts collected between Nov 1979-81 at a concentration of 9150 ng/ul(1). 2-Naphthylamine was identified at a concentration of 43.6 mg/g in a basic fraction sample of HYGAS low-temperature reactor tar from a HYGAS coal gasification plant in Chicago(2). 2-Naphthylamine was found in the waste streams of the Sumida River, Japan where it has been produced and used and has been reported to be present in the effluent from certain dyestuffs factories(3).

URBAN/SUBURBAN: 2-Naphthylamine has been detected in airborne pollutants(1). The concentration of 2-naphthylamine in outdoor air from the Brindisi Centre in the province of Florence, Italy was below 1 ng/cu m(2).|INDOOR: The concentration of 2-naphthylamine in indoor air from an office with smokers in the province of Florence, Italy was below 1 ng/cu m(1).

Cigarette smoke has been reported to contain 0.02 ug 2-naphthylamine per cigarette(1). In a different study, the concentration of 2-naphthylamine was 0.002 ug per cigarette in mainstream smoke(2). The study reported that there is 20 to 30 times more 2-naphthylamine in sidestream cigarette smoke than in mainstream cigarette smoke.

moderately toxic

Pentachlorophenol, a known inhibitor of hepatic sulfotransferases, caused a 2-3 fold increased in urinary levels of n-hydroxy-2-naphthylamine and its glucuronide conjugate from 2-naphthylamine treated rats.

The lowest dose to induce a carcinogenic response is reported as 18 mg/kg.|Oncogenic transformation human cell types 68 mg/L.|DNA inhibition HeLa cell 200 umol/L.

Individuals with reduced immunological competence, those undergoing treatment with steroids or cytotoxic agents, pregnant women, and cigarette smokers.

2-Naphthylamine is not reported to occur naturally in the environment(1).

2-Naphthylamine's production and use in the manufacture of rubber and dyes(1,2) and as an antioxidant(3) may have resulted in its direct release to the environment(SRC). However as of 1976 it was no longer produced or consumed commercially in the US(4). 2-Naphthylamine has been found in emissions from industries where nitrogen-containing organic matter is pyrolyzed(3). It is found in cigarette smoke (0.02 ug/cigarette)(2,5). 2-Naphthylamine is also found in coal tar and as contaminant (impurity) in commercial 1-naphthylamine(5).

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 1,000(2), indicates that 2-naphthylamine is expected to have low mobility in soil(SRC). Results of a batch equilibrium study with various soils indicated that 1-naphthylamine, which is structurally analogous to 2-naphthylamine, binds to soil in two phases with an initial rapid and reversible equilibrium established between the amine and the inorganic and organic components of soil followed subsequently by a strong association with the humic fraction of soil via covalent binding(3,4). Volatilization of 2-naphthylamine from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 8.10X10-8 atm-cu m/mole(5). 2-Naphthylamine is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 2.56X10-4 mm Hg(6). Based on primary soil biodegradation and mineralization studies, 2-naphthylamine is expected to biodegrade slowly in soil(7,8).|AQUATIC FATE: Based on a classification scheme(1), a Koc value of 1,000(2), indicates that 2-naphthylamine is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 8.10X10-8 atm-cu m/mole(4). The pKa of 2-naphthylamine is 4.16(5), indicating that this compound will partially exist as a cation in the environment. According to a classification scheme(6), an estimated BCF of 11(SRC), from a log Kow of 2.28(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Based on primary soil biodegradation and mineralization studies, 2-naphthylamine is expected to biodegrade slowly in water(9,10).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-naphthylamine, which has a vapor pressure of 2.56X10-4 mm Hg at 25 deg(2) is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-naphthylamine 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 1.9 hours(SRC), calculated from its rate constant of 2.0X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 2-Naphthylamine was shown to photolyze in direct sunlight with half-lives ranging from 0.05 to 0.19 hours(4).

The rate constant for the vapor-phase reaction of 2-naphthylamine with photochemically-produced hydroxyl radicals has been estimated as 1.0X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1.9 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The half-lives for 2-naphthylamine particles adsorbed onto silica and alumina plates in a fluidized bed photoreactor ranged from 0.20 to 10.8 hours under UV light and from 0.05 to 0.19 hours in direct sunlight(2). 2-Naphthylamine is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3).

An estimated BCF of 11 was calculated for 2-naphthylamine(SRC), using a log Kow of 2.28(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

The measured Koc for 2-naphthylamine is 1,000(1). According to a classification scheme(2), this Koc value suggests that 2-naphthylamine is expected to have low mobility in soil. Results of a batch equilibrium study with various soils indicated that 1-naphthylamine, which is structurally analogous to 2-naphthylamine, binds to soil in two phases with an initial rapid and reversible equilibrium established between the amine and the inorganic and organic components of soil followed subsequently by a strong association with the humic fraction of soil via covalent binding(3,4). Aminonaphthalenes are known to form complexes with soil matter(5). The pKa of 2-naphthylamine is 4.16(6), indicating that this compound will partially exist in cation form in the environment.

The Henry's Law constant for 2-naphthylamine is 8.10X10-8 atm-cu m/mole(1). This Henry's Law constant indicates that 2-naphthylamine is not expected to volatilize from moist soil or water surfaces(2). 2-Naphthylamine is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 2.56X10-4 mm Hg(3).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 275 workers (265 of these are female) were potentially exposed to 2-naphthylamine in the US(1). Occupational exposure and general population exposure should be low or non-existent since 2-naphthylamine is no longer produced or used(SRC). The general population may be exposed to 2-naphthylamine through the inhalation of cigarette smoke(2). Gas retort houses have been shown to have atmospheric levels of 2-naphthylamine to give a human exposure of 0.2 ug/day(2).

Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included. (See all compounds classified as Carcinogens.)

It /(2-naphthylamine)/ is readily absorbed through the skin and by inhalation.|A three-compartment pharmacokinetic model was developed with a computer to separate absorption, metabolism and distribution of n-hydroxy-2-naphthylamine in intact animal from events in bladder lumen (deposition, hydrolysis, and resorption). Total bladder exposure to carcinogen, N-hydroxy-2-naphthylamine, was simulated; and urine pH and voiding interval, both of which differ among species, were tested as variables. For humans and dogs, urine ph was found to be more acidic than monkeys or rats; while voiding intervals in rats were shorter than in monkeys, dogs, or humans. Relative species susceptibilities, indicated by model as total bladder exposure to hydroxy metab under conditions of normal urine pH and frequency of micturition for each species were: human greater than or equal to dog greater than monkey greater than rat. This is consistent with reported carcinogenic potency of 2-naphthylamine in these species and suggests that urine pH and voiding interval are important factors in bladder cancer.|2-Naphthylamine metabolism occurs through oxidation to form 2-amino-1-naphthol. At least 10 metabolites of 2-naphthylamine have been identified in the urine of rats and rabbits. In these animals, 70-80% of metabolites are removed with the urine, 20-30% are excreted in the feces.

... Beta-naphthylamine ... is transformed into bis(2-amino-1-naphthyl)hydrogen phosphate and excreted ... Its hydrolysis in body to 2-amino-1-naphthol is thought to be responsible for carcinogenic activity ...|... Although metabolite, 2-amino-1-naphthylsulfuric acid is resistant to hydrolysis by urinary arylsulfatase, glucuronide and phosphate conjugates are hydrolyzed in bladder to give free ortho-aminonaphthol.|Incubation of 2-naphthylamine with rat liver microsomes fortified with NADPH resulted in formation of two types of free radicals which were identified as n-hydroxy-2-naphthylamine and 2-amino-1-naphthol. The former radical was oxidized to 2-nitrosonaphthalene radical. Amount of metabolites produced could be increased by using microsomes from phenobarbital induced rats.|In vitro metabolic n-oxidation of 2-naphthylamine investigated with intact dog bladder, whole intact bladder mucosa and microsomes from this tissue. Very low levels of metabolic n-oxidation were detected. No n-oxidation by these tissue preparations was observed using GLC. Concentration of n-oxidized metabolism observed in urine of exposed dogs suggest that n-oxidation takes place predominately in liver and that the bladder plays, at most, a minor role in formation of the presumed proximate urinary carcinogens.|For more Metabolism/Metabolites (Complete) data for 2-NAPHTHYLAMINE (12 total), please visit the HSDB record page.|2-naphthylamine has known human metabolites that include N-Hydroxy-2-naphthalenamine.

beta-Naphthylamine (BNA)... is a stimulatory agent of respiratory burst in rat peritoneal macrophages besides being a potent carcinogen. Since polymixin-B and staurosporine are inhibitors of protein-kinase-C (PKC), the data suggest that PKC may be involved in the intracellular signal transduction pathway of BNA stimulated superoxide production.|N-oxidation by cytochrome p450 enzymes is an initial step in the metabolic activation of aromatic amine compounds. Once metabolized, these compounds are converted to DNA-reactive species which can exhibit potent mutagenic and/or carcinogenic activity. The precise mechanism of P450 enzyme oxidation is not completely understood, although various theories, involving either one-electron transfer, two-electron transfer or addition-rearrangement, have been debated. In previous studies, selection of the most probable mechanism has been based on consideration of Huckel theory charge distribution calculations and experimentally-derived enzyme metabolism data. This approach can now be improved by incorporating contemporary, ab initio quantum chemical methods to accurately determine the chemical properties of P450 aromatic amine substrates. ...This work ... compare/ed/ the experimental oxidation yields and rates of 1-naphthylamine (1-NA), 2-naphthylamine (2-NA) and 2-aminofluorene (2-AF). This data was then analyzed with respect to ab initio-calculated charge distributions and energies of reactants, oxidation products and proposed intermediates. ...Analysis of theoretical and experimental data indicates that the one-electron model is more consistent with oxidation rate data for 1-NA, 2-NA, and 2-AF. ...In contrast to earlier studies, the one-electron mechanism is more likely to be the pathway for P450-catalyzed aromatic amine oxidation.

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. (ERG, 2016)|Carcinogens, Mutagens

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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)|(See procedures)

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer immediately for medical attention .

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

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. 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 mg/kg up to 200 mL of water for dilution if the patent can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . Cover skin bums with dry sterile dressings after decontamination ... . /Organic bases/Amines and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or has severe pulmonary edema. 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. Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. If patient is unresponsive to these measures, vasopressors may be helpful. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic bases/Amines and related compounds/

/HUMAN EXPOSURE STUDIES/ Toxic by ingestion, inhalation, and skin absorption.|/HUMAN EXPOSURE STUDIES/ ...It has been estimated that cigarette smoking accounts for 25-70% (the estimated ranges in three different reports were: 25-60%, 30-50%, and 40-70%) of all cases of bladder cancer... in industrialized developed countries with aromatic amines such as ...2-naphthylamine as the prime suspect causative carcinogens.|/HUMAN EXPOSURE STUDIES/ To investigate the effects of benzidine (BZ) and beta-naphthylamine (BNA) on the immune system in man, the activity of natural killer (NK) cells as well as the relative number (percentage) of Leu 11a positive cells in peripheral blood lymphocytes were measured in 63 dyestuff workers exposed to BZ and BNA (aromatic amines, AA). The cytotoxic potential per NK cell (unit NK cell activity) was approximated by dividing the NK activity per fixed numbers of unseparated mononuclear cells by the percentage of Leu 11a positive lymphocytes that mediated NK activity. Thirty one of these workers had previously been treated for bladder cancer and then cured (ex-cancer AA workers) whereas the remaining 32 had not been diagnosed as having bladder cancer (non-cancer AA workers). There was no significant difference in the gross NK activity per unseparated peripheral mononuclear cells among ex-cancer AA workers, non-cancer AA workers, and the control group (p greater than 0.05). The relative number of Leu 11a positive cells, on the other hand, was significantly higher in AA workers than in the control group (p less than 0.01). The unit NK cell activity, as a result, was significantly more reduced in both ex-cancer and non-cancer AA workers than in the control group (p less than 0.05 and p less than 0.01, respectively). Between ex-cancer and non-cancer AA workers, no significant difference was observed in terms of unit NK cell activity. These results indicated that the function of NK cells per se was impaired in AA workers whereas the number of circulating NK cells was relatively increased.|/HUMAN EXPOSURE STUDIES/ A study of morbidity among former employees and family members of a Superfund site was initiated because of concern for possible exposure to beta-naphthylamine (BNA). The site, known as the Drake Superfund site, was located at Lock Haven, Pennsylvania. The study group consisted of 79 former workers (75 males) at the site and 71 family members. The subjects were interviewed by questionnaire to obtain information on demographic characteristics, personal health, occupational history, and occupational and environmental exposures. Urine samples were collected to screen for signs of possible hepatic, pancreatic, and urogenital conditions. Statistically significant health outcomes related to work at the site were irritation conditions among 34 employees who reported being exposed to herbicides or pesticides, and cancer (including one case of bladder cancer) among 12 employees exposed to BNA before 1962. Nine subjects tested positive for bladder cancer on one of two urine screening tests; however, only one subject tested positive on both tests. Death certificates obtained for 20 of 28 former employees who died before the survey indicated that five deaths were due to cancer, with two from bladder cancer. The authors conclude that two health risks, cancer among workers exposed to BNA before 1962 and irritation conditions among those exposed to herbicides and pesticides, can be related to work at the Drake site. A comprehensive health registry and medical surveillance program for the subjects has been established.|For more Human Toxicity Excerpts (Complete) data for 2-NAPHTHYLAMINE (19 total), please visit the HSDB record page.

2 Aminonaphthalene

The substance can be absorbed into the body by inhalation, through the skin and by ingestion.|inhalation, skin absorption, ingestion, skin and/or eye contact

dermatitis; hemorrhagic cystitis; dyspnea (breathing difficulty); ataxia; methemoglobinemia, hematuria (blood in the urine); dysuria; [potential occupational carcinogen]

Blue lips, fingernails and skin. Confusion. Dizziness. Convulsions. Headache. Nausea. Unconsciousness.

MAY BE ABSORBED! Redness. Further see Inhalation.

Bladder, skin

... No longer commercially produced or used in the United States.|The rodenticide ANTU (alpha-naphthylthiourea) was used in the United Kingdom mainly in the late 1940s and early 1950s. The product /at that time/ contained up to 0.2% of beta-naphthylamine as an impurity, and it was finally withdrawn in 1967 as a suspected carcinogen. Fourteen cases of urothelial tumors among rodent operatives /were/ reported.

A HIGH SPEED LIQUID CHROMATOGRAPHIC PROCEDURE WAS ESTABLISHED FOR DETERMINING BETA-NAPHTHYLAMINE IN COSMETIC COAL-TAR COLORS WITH A DETECTION LIMIT OF 5 PPB BY USING ALPHA-NAPHTHYLAMINE AS AN ALTERNATE STANDARD.|A GAS CHROMATOGRAPHIC METHOD IS DISCUSSED FOR DETERMINING TRACE AMT OF 2-NAPHTHYLAMINE IN 1-NAPHTHYLAMINE.|1 TO 5-RING PRIMARY AROMATIC AMINES MAY BE SEPARATED ACCORDING TO THEIR RELATIVE BASICITIES BY USE OF A CATION HIGH PERFORMANCE LIQUID CHROMATOGRAPHIC PROCEDURE. THIS PROCEDURE WAS SUCCESSFUL IN ISOLATION OF MUTAGENIC COMPONENTS FROM A COMPLEX MIXTURE OF BASES DERIVED FROM A PROCESS STREAM FROM A COAL GASIFICATION PILOT PLANT.|PRIMARY & SECONDARY AROMATIC AMINES PRESENT IN INDUSTRIAL WASTE CAN BE DETERMINED BY GAS CHROMATOGRAPHY.|For more Analytic Laboratory Methods (Complete) data for 2-NAPHTHYLAMINE (8 total), please visit the HSDB record page.

A CHROMATOGRAPHIC DETECTION METHOD BASED ON THE REACTION OF ELUTED COMPD WITH FE3+-BATHOPHENANTHROLINE COLORIMETRIC REAGENT IN A POSTCOLUMN REACTOR WAS APPLIED TO ANALYSIS OF TOXIC N-OXIDIZED URINARY METAB OF RHESUS MONKEYS TREATED WITH 1- & 2-NAPHTHYLAMINE. THESE COMPOUNDS ARE OXIDIZED TO N-HYDROXYARYLAMINES IN THE LIVER, CONJUGATED AS N-GLUCURONIDE, & EXCRETED IN THE URINE. N-GLUCURONIDE UNDERGOES ACIDIC HYDROLYSIS IN URINE TO RELEASE FREE N-HYDROXYARYLAMINE, AN ULTIMATE CARCINOGEN FOR INDUCTION OF BLADDER TUMORS. IN THIS STUDY, N-HYDROXY-N-GLUCURONIDE OF 2-NAPHTHYLAMINE WAS EXCRETED AT A RATE THAT WAS 6.8 TIMES THAT OF 1-NAPHTHYLAMINE ISOMER. THIS IS CONSISTENT WITH MUCH HIGHER CARCINOGENICITY OF BETA ISOMER IN A VARIETY OF SPECIES.

Health Hazards -> Carcinogens, Mutagens