8-Hydroxyquinoline

145.15800

145.16

205-711-1

5UTX5635HP

615011|402623|285166|2039

2811

DTXSID5020730

White crystals or white crystalline powder

A - Alimentary tract and metabolism|D - Dermatologicals|G - Genito urinary system and sex hormones|R - Respiratory system

2933499090

33.12000

2

white to pale yellow crystal

1.034 g/cm³ @ Temp: 20 °C

73-75 °C

267 °C (approx)

100ºC

1.4500 (estimate)

H2O: INsoluble

Store at RT.

1.66X10-3 mm Hg @ 25 deg C

LD50 orally in Rabbit: 1200 mg/kg

Phenolic odor

5.017|pKa 5.017; Ka 1.21X10-6 at 20 °C|pKa1= 5.017; pKa2= 9.812 (conjugate acid)

123.6 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Readily forms stable metal chelates|Usually tan /Technical grade/|Pale yellow, crystalline powder; slight saffron odor; burning taste; MP: 175-178 °C; freely sol in water; insol in ether; sol in about 100 parts glycerol; slightly sol in alcohol /8-Hydroxyquinoline sulfate/|Darkens when exposed to light

Insoluble in water.

Amines, Phosphines, and Pyridines

8-HYDROXYQUINOLINE darkens on exposure to light. This chemical readily forms stable metal chelates. It is incompatible with strong oxidizers. It is also incompatible with many metal ions. (NTP, 1992)

III

9

2811

3

R22; R36/37/38; R68

S26-S36/37/39-S45

VC4200000

Xn

DARKENS WHEN EXPOSED TO LIGHT.

P261, P264, P270, P271, P301+P312, P304+P312, P304+P340, P312, P330, P501

H302

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Toxicology Review; Internist 15 (1): 7 (1974)|Toxicology Review; Archives of Environmental Health 23: 6 (1971)|DHHS/NTP; Toxicology & Carcinogenesis Studies of 8-Hydroxyquinoline in F344/N Rats and B6C3F1 Mice (Feed Studies) Technical Report Series No. 276 (1985) NIH Publication No. 85-2532

Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)

|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P261, P264, P270, P272, P273, P280, P281, P301+P310, P302+P352, P305+P351+P338, P308+P313, P310, P321, P330, P333+P313, P363, P391, P405, and P501|H301 (61.35%): Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P261, P264, P270, P272, P273, P280, P281, P301+P310, P301+P312, P302+P352, P305+P351+P338, P308+P313, P310, P321, P330, P333+P313, P363, P391, P405, and P501|Aggregated GHS information provided by 447 companies from 19 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P261, P264, P270, P272, P273, P280, P281, P301+P312, P302+P352, P305+P351+P338, P308+P313, P310, P321, P330, P333+P313, P363, P391, P405, and P501|P264, P270, P280, P301+P312, P302+P352, P305+P351+P338, P312, P322, P330, P337+P313, P361, P363, P405, and P501

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-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)

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should protect this material from exposure to light, and store it in a refrigerator. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Combustible when exposed to heat or flame.

AFTER LETHAL IM DOSES IN MICE (30 MG/KG) INJECTED D-PENICILLAMINE (1 G/KG) PREVENTED /TOXIC/ SYMPTOMS & DEATH BUT NOT TRANSIENT HYPERGLYCEMIA.|THE INFLUENCE OF RADIOPROTECTORS, CYSTEAMINE & AMINOETHYLISOTHIOURONIUM AS WELL AS OF THE AMINO ACIDS L-ALANINE, L-CYSTEINE, L-ARGININE, L-ASPARAGINE, L-GLUTAMIC ACID, L-HISTIDINE, & L-METHIONINE, ON THE CYTOGENETIC ACTION OF 8-HYDROXYQUINOLINE SULFATE WAS TESTED IN HUMAN LYMPHOCYTE CULTURES IN VITRO. EXCESS L-CYSTEINE, CYSTEAMINE, & L-ASPARAGINE ADDED SIMULTANEOUSLY WITH 8-HYDROXYQUINOLINE SULFATE DISTINCTLY REDUCED THE CHROMOSOME. DAMAGING EFFECT OF 8-HYDROXYQUINOLINE. L-GLUTAMIC ACID & AMINOETHYLISOTHIOURONIUM EXERTED LESSER PROTECTIVE ACTIVITY. L-METHIONINE DISPLAYED SOME EFFECT ONLY IN REDUCING THE RELATIVELY RARE ISOCHROMATID ABERRATIONS INDUCED BY 8-HYDROXYQUINOLINE SULFATE. THE OTHER AMINO ACIDS HAD NO EFFECT.|The formation of DNA-strand breaks was studied in cultured human lung cells (A 549) subjected to iron, either in the form of iron(III) citrate or in combination with the metal chelators ethylene diamine tetra-acetic acid (EDTA), nitrilo triacetic acid (NTA), or 8-hydroxyquinoline (8HQ). After 15 min exposure to 5 uM iron(III) citrate or iron chelate, the cellular levels of iron were found to be three times higher in cells subjected to iron-8HQ than in cells subjected to iron(III) citrate, iron-EDTA or iron-NTA. Exposure to iron-8HQ caused extensive DNA-strand breakage, whereas no such breakage was found in cells exposed to iron-EDTA or iron-NTA. The DNA damage caused by iron-8HQ increased with time and dose, and DNA-strand breakage was clearly demonstrable in cells after 15 min exposure to as little as 0.1 uM iron-8HQ. Moreover, iron-8HQ was strongly toxic to the cells and inhibited their growth after exposure. Along with the formation of DNA-strand breaks, the concentration of cellular malondialdehyde increased four-fold after exposure to iron-8HQ and two-fold after exposure to iron-EDTA or iron-NTA, suggesting that reactive oxygen metabolites might be involved in the toxic action. Moreover, both iron-EDTA and iron-NTA caused a considerable hydroxylation of deoxyguanosine (dG) residues in DNA in vitro, whereas iron(III) citrate and iron-8HQ only caused a minor hydroxylation of dG. This points to the possibility that iron-8HQ-mediated DNA-strand breakage in cells might be due to the action of a metal-bound oxyl radical formed from the iron-8HQ complex rather than to the formation of hydroxyl radicals. Altogether, these findings indicate that iron bound to the lipophilic chelator, 8HQ, has strong toxic properties and that it may cause substantial DNA-strand breakage and lipid peroxidation in living cells.

LD50 Rat oral 1200 mg/kg|LD50 Mice ip 48 mg/kg|LD50 Rat ip 50 mg/kg|LD50 Mouse sc 83,600 ug/kg|For more Non-Human Toxicity Values (Complete) data for 8-HYDROXYQUINOLINE (6 total), please visit the HSDB record page.

8-Hydroxyquinoline, given at 1500-3000 ppm in the feed of male and female F344/N rats and B6C3F1 mice for 103 wk, showed no evidence of carcinogenicity. Survival was similar to that of controls, with slight decreases in appetite and body weight with the high dose level.

... IS NOT KNOWN TO OCCUR IN NATURE.

8-Hydroxyquinoline's production and use as a chemical intermediate(1-3) and in steel electroplating(4) may result in its release to the environment through various waste streams(SRC). It's former use as a fungicide(5) may have resulted in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 3,000(SRC), determined from a structure estimation method(2), indicates that 8-hydroxyquinoline is expected to have slight mobility in soil(SRC). Volatilization of 8-hydroxyquinoline from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.7X10-7 atm-cu m/mole(SRC), based upon its vapor pressure, 1.66X10-3 mm Hg(3), and water solubility, 556 mg/l(4). 8-Hydroxyquinoline is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Biodegradation in soil is not an important environmental fate process based on a 0% theoretical BOD using sewage sludge(5).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3,000(SRC), determined from a structure estimation method(2), indicates that 8-hydroxyquinoline is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 5.7X10-7 atm-cu m/mole(SRC) derived from its vapor pressure, 1.66X10-3 mm Hg(4) and water solubility, 556 mg/l(5). According to a classification scheme(6), an estimated BCF of 7(SRC), from its log Kow of 2.02(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). To test for photolytic degradation in aqueous solution, 8-hydroxyquinoline was illuminated with filtered light, simulating daylight(9). The half-life for the photolytic degradation of 8-hydroxyquinoline ranged from 40-64 hours. Biodegradation in water is not an important environmental fate process based on a 0% theoretical BOD using sewage sledge(10).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 8-hydroxyquinoline, which has a vapor pressure of 1.66X10-3 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 8-hydroxyquinoline 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 2.0 hrs(SRC), calculated from its rate constant of 2.0X10-10 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). 8-Hydroxyquinoline is expected to undergo photolysis in the atmosphere based upon aquatic photolytic experiments. The half-life for the photolytic degradation of 8-hydroxyquinoline in aqueous solution illuminated with filtered light, simulating daylight, ranged from 40-64 hours(4).

The rate constant for the vapor-phase reaction of 8-hydroxyquinoline with photochemically-produced hydroxyl radicals has been estimated as 2.0X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2.0 hrs at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 8-Hydroxyquinoline is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2). To test for photolytic degradation in aqueous solution, 8-hydroxyquinoline was illuminated with filtered light, simulating daylight(3). The half-life for the photolytic degradation of 8-hydroxyquinoline ranged from 40-64 hours.

An estimated BCF of 7 was calculated for 8-hydroxyquinoline(SRC), using a log Kow of 2.02(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).

Using a structure estimation method based on molecular connectivity indices(1), the Koc for 8-hydroxyquinoline can be estimated to be 3,000(SRC). According to a classification scheme(2), this estimated Koc value suggests that 8-hydroxyquinoline is expected to have slight mobility in soil.

The Henry's Law constant for 8-hydroxyquinoline is estimated as 5.7X10-7 atm-cu m/mole(SRC) derived from its vapor pressure, 1.66X10-3 mm Hg(1), and water solubility, 556 mg/l(2). This Henry's Law constant indicates that 8-hydroxyquinoline is not expected to volatilize from water surfaces(3). 8-Hydroxyquinoline estimated Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). 8-Hydroxyquinoline is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 13,728 workers (9,645 of these are female) were potentially exposed to 8-hydroxyquinoline in the US(1). Occupational exposure to 8-hydroxyquinoline may have occured through inhalation of dust and dermal contact with this compound at workplaces where 8-hydroxyquinoline was produced or used(SRC).

Oxyquinoline is used as a biocidal component of several over the counter products. These products are marketed for the purposes of inhibiting abnormal biological growth in the vagina and restoring natural pH.

A BACTERIOSTATIC & FUNGISTATIC COMPOUND; USED PRINCIPALLY IN TREATMENT OF MINOR BURNS & OF HEMORRHOIDS.|OXYQUINOLINE SULFATE ... IS ... USED ... IN TREATMENT OF ATHLETE'S FOOT, VAGINITIS, & AS A GARGLE, EYEWASH, NASAL DOUCHE, & IN HEMORRHOIDAL PREPARATIONS ... /OXYQUINOLINE SULFATE/|/OVER THE COUNTER/ HYDROXYQUINOLINE IS 1 OF 4 ANTIFUNGAL AGENTS RECOMMENDED FOR ACTIVE TREATMENT OF FUNGUS ASSOCIATED WITH DIAPER RASH & PRICKLY HEAT IN BABIES. /HYDROXYQUINOLINE/|8-HYDROXYQUNIOLINE SULFATE INHIBITED FORMATION OF ARTIFICIAL CALCULUS IN VITRO & RAT CALCULUS IN VIVO. IN RATS, IT PREVENTED CALCULUS FORMATION WHEN APPLIED BY SWABBING OR BY INTRAORAL INSTILLATION. IN DOGS, FORMATION OF DENTAL PLAQUE WAS INHIBITED 33 TO 98% IN COMPARISON TO PLACEBO. ALSO, 25 TO 58% OF ESTABLISHED PLAQUE ACCUMULATIONS WERE REMOVED, WHEREAS PLACEBO REMOVED 2 TO 22%.|For more Therapeutic Uses (Complete) data for 8-HYDROXYQUINOLINE (7 total), please visit the HSDB record page.

Oxyquinoline acts as a biocide to eliminate bacteria and fungi.

Oxyquinoline is excreted in both the primarily in the urine with some in the bile.|IN RATS /MALE, DONRYU STRAIN, IV INJECTION/ 8-HYDROXYQUINOLINE WAS METABOLIZED TO GLUCURONIDE & SULFATE CONJUGATES. MORE 8-HYDROXYQUINOLINE GLUCURONIDE WAS EXCRETED IN URINE THAN 8-HYDROXYQUINOLINE SULFATE CONJUGATE. ONLY THE GLUCURONIDE CONJUGATE WAS EXCRETED IN BILE.|8-HYDROXYQUINOLINE WAS METABOLIZED TO GLUCURONIDE & SULFATE CONJUGATES AFTER IV ADMIN IN RATS /MALE, DONRYU STRAIN/. THE GLUCURONIDES WERE EXCRETED IN BILE & URINE, BUT THE SULFATES WERE EXCRETED EXCLUSIVELY IN THE URINE. UNMETABOLIZED FORMS WERE ONLY SLIGHTLY EXCRETED.

In the urine, 60% of the dose is excreted as glucuronide conjugates and 23% of the dose as sulfate conjugates. In the bile, 9% of the total dose is found as glucuronide conjugates.|IN RATS /MALE, DONRYU STRAIN, IV INJECTION/ 8-HYDROXYQUINOLINE WAS METABOLIZED TO GLUCURONIDE & SULFATE CONJUGATES.|8-HYDROXYQUINOLINE WAS METABOLIZED TO GLUCURONIDE & SULFATE CONJUGATES AFTER IV ADMIN IN RATS /MALE, DONRYU STRAIN/. UNMETABOLIZED FORMS WERE ONLY SLIGHTLY EXCRETED.

The mechanism by which oxyquinoline exerts its biocidal effect is unknown.

SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes, mucous membranes and respiratory tract. It also causes irritation of the gastrointestinal tract. ACUTE/CHRONIC HAZARDS: This compound is toxic by ingestion. It may be harmful by inhalation or skin absorption. It is an irritant of the skin, eyes, IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. 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. (NTP, 1992)

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. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. 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. (NTP, 1992)

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 ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Aromatic hydrocarbons and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aromatic hydrocarbons and related compounds/

VARIOUS HALOGENATED DERIVATIVES USED IN TREATING AMEBIASIS IN MAN ARE ... COMPARATIVELY BENIGN EXCEPT FOR FREQUENT ALLERGIC REACTIONS ... /8-HYDROXYQUINOLINE SULFATE/

8 Hydroxyquinoline

USEPA/OPP Pesticide Code 059803; Trade Names: Fennosan H 30, NCI-C55298, Tumex, USAF EK-794, Quinophenol.|... AVAILABLE IN USA IN TECHNICAL & REAGENT GRADES. IT IS ALSO AVAILABLE AS 0.5% SOLN (OR AEROSOL) SUITABLE FOR TOPICAL USE.

8-Quinolinol: ACTIVE|... /Has been/ discontinued by Ashland Chemical Co.|BACTERIOSTATIC & ANTIMYCOTIC ACTIVITY OF 8-HYDROXYQUINOLINE SULFATE IN DERMATOSES IS BLOCKED BY INCORPORATION OF 8-HYDROXYQUINOLINE SULFATE IN EXSICCANT PASTE SR71, ZINC OXIDE-OIL, & ZINC OXIDE LOTION. IT IS NOT RELEASED OR IS RELEASED IN ONLY SMALL AMOUNTS FROM LIPOPHILIC BASES (EXCEPT OLEOGELS), PREPARATIONS WITH EXTERNAL LIPID PHASE & ZINC OXIDE-CONTAINING VEHICLES. /8-HYDROXYQUINOLINE SULFATE/

A spectrophotometric procedure is described for the detection of 8-hydoxyquinoline and three of its halogenated derivatives: clioquinol, iodoquinol, and chiniofon. The proposed method involves the use of 2,6-dichloroquinone chlorimide as the chromogenic reagent. 8-Hydroxyquinoline produces a blue color peaking at 595 nm and the other compounds yield a green-blue color with max absorption at 650 nm. The colors produced obey Beer's law. The procedure was applied to the detection of the compounds in dosage forms.|Of 6 colorimetric methods for the determination of 8-hydroxyquinoline in pharmaceutical products and tissues, one using Gibbs reagent (2,6-dibromo-benzoquinone chlorimine) was reported to be the most sensitive, with a detection limit of 0.5 ug/l. A colorimetric method for its determination in galenical preparations containing other phenols is based on its complex with a vanadium ion. Non-aqueous titration methods have been described to determine 8-hydroxyquinoline and its oxidation products and to determine 8-hydroxyquinoline and some of its metal chelates. An aqueous titration method for the determination of 8-hydroxyquinoline sulfate has been outlined and it can be determined fluorimetrically as its chelate compound with tin(2+). A fluorimetric determination of 8-hydroxyquinoline is based on its luminescence in sulfuric acid at 77 deg K and has a sensitivity of 0.12 uM. A spectrophotometric method for the determination of 8-hydroxyquinoline as the copper chelate can be used in the presence of some other metals. Paper, thin-layer and gas-liquid chromatography can also be used to determine 8-hydroxyquinoline.

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