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C.I. Direct Red 2

PubChem CID
13816
Structure
C.I. Direct Red 2_small.png
C.I. Direct Red 2_3D_Structure.png
Molecular Formula
Synonyms
  • 992-59-6
  • Benzopurpurine 4B
  • C.I. Direct Red 2
  • DIRECT RED 2
  • Benzopurpurin 4B
Molecular Weight
724.7 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-07-19
  • Modify:
    2025-01-11
Description
Direct red 2 is a brown to dark red powder. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
C.I. Direct Red 2.png

1.2 3D Conformer

3D Conformer of Parent

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

disodium;4-amino-3-[[4-[4-[(1-amino-4-sulfonatonaphthalen-2-yl)diazenyl]-3-methylphenyl]-2-methylphenyl]diazenyl]naphthalene-1-sulfonate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C34H28N6O6S2.2Na/c1-19-15-21(11-13-27(19)37-39-29-17-31(47(41,42)43)23-7-3-5-9-25(23)33(29)35)22-12-14-28(20(2)16-22)38-40-30-18-32(48(44,45)46)24-8-4-6-10-26(24)34(30)36;;/h3-18H,35-36H2,1-2H3,(H,41,42,43)(H,44,45,46);;/q;2*+1/p-2
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

SUXCALIDMIIJCK-UHFFFAOYSA-L
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=CC=CC=C4C(=C3)S(=O)(=O)[O-])N)C)N=NC5=C(C6=CC=CC=C6C(=C5)S(=O)(=O)[O-])N.[Na+].[Na+]
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C34H26N6Na2O6S2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

992-59-6

2.3.2 Deprecated CAS

1079993-65-9, 1082260-20-5, 179472-45-8, 70248-71-4
179472-45-8, 70248-71-4

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEMBL ID

2.3.6 DSSTox Substance ID

2.3.7 Nikkaji Number

2.3.8 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • benzopurpurine 4B
  • C.I. direct red 2
  • direct red 2

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
724.7 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
12
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
724.11506348 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
724.11506348 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
233 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
50
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
1250
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
3
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Direct red 2 is a brown to dark red powder. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
Brown or dark red solid; [HSDB] Powder; [MSDSonline]

3.2.2 Color / Form

BROWN POWDER
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 185
Dark-red powder
Green FJ; The Sigma-Aldrich Handbook of Stains, Dyes and Indicators. Milwaukee, WI: Aldrich Chemical Company, Inc. p. 135 (1990)

3.2.3 Melting Point

554 °F (decomposes) (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

3.2.4 Solubility

less than 1 mg/mL at 61 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
SOL IN WATER, SODIUM HYDROXIDE, SULFURIC ACID, ETHANOL, ACETONE, CELLOSOLVE; PRACTICALLY INSOL IN OTHER ORGANIC SOLVENTS
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 185
20 mg/ml in water; 70 mg/ml in 2-methoxyethanol; 3 mg/ml in ethanol
Green FJ; The Sigma-Aldrich Handbook of Stains, Dyes and Indicators. Milwaukee, WI: Aldrich Chemical Company, Inc. p. 135 (1990)

3.2.5 Other Experimental Properties

As pH indicator, violet 1.2 to red 4.0.
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 185

3.3 Chemical Classes

Dyes -> Benzidine Dyes

4 Spectral Information

4.1 UV Spectra

Absorption peak at 500 nm in water.
Green FJ; The Sigma-Aldrich Handbook of Stains, Dyes and Indicators. Milwaukee, WI: Aldrich Chemical Company, Inc. p. 135 (1990)

6 Chemical Vendors

7 Pharmacology and Biochemistry

7.1 Absorption, Distribution and Excretion

... Excretion profiles based on parallel HPLC and radioassays of feces from rats dosed with (14)C labeled Direct Blue 15 or Direct Red 2 are presented. Based on these radioassays, about 74% of each dose was excreted via the feces; however, HPLC assays showed that only about 11% of each dose was present as intact dye in the excretement.
Levine RA et al; J Anal Toxicol 6 (4): 157-63 (1982)

7.2 Metabolism / Metabolites

absorption, metabolism and tissue distribution studies were conducted in the rat with (14)C-biphenyl ring labeled Direct Blue 15, a 3,3'-dimethoxybenzidine (DiMxBzd) based azo dye; Direct Red 2, based on 3,3'-dimethylbenzidine (DiMeBzd) and the corresponding benzidine congener amines. Single oral doses of (14)C labeled dyes (12 mg/kg) and molar equivalent doses of respective amines were admin, and urine and fecal samples collected at intervals up to 192 hr. ... A comparison of the metabolism of Direct Blue 15 with its base DiMxBzd, indicated the base was more extensively metabolized and that most of the (14)C in various extracts was identified in known metabolites. The metabolism of Direct Red 2 compared with its base DiMeBzd, indicated that the base was more extensively metabolized , yet only a small percentage of the (14)C in extracts was identified as known metabolites. Most of the (14)C present in the urine could not be extracted with benzene or chloroform, indicating high polarity. Distribution studies conducted with both dyes showed that the liver, kidney and lung accumulated and retained higher levels of (14)C than other tissues (at 72 hr). Peak levels of (14)C, which occurred 8-12 hr after dosing, were significantly higher with Direct Red 2 than Direct Blue 15. Tissue distribution data (72 hr for rats dosed with free amines compared with the dyes showed a generally lower but similar distribution pattern.
Bowman KC et al; J Anal Toxicol 6 (4): 164-74 (1982)
The metabolism of a benzidine based dye, Direct Black 38, a 3,3'-dimethylbenzidine based dye, Direct Red 2, and a 3,3'-dimethoxybenzidine based dye, Direct Blue 15, was studied both in pure cultures of anaerobic bacteria and in bacterial suspensions derived from intestinal contents of the rat. All of the pure cultures and the rat intestinal bacteria were able to reduce the azo linkages of Direct Black 38, Direct Red 2 and Direct Blue 15 with the subsequent formation of benzidine, 3,3'-dimethylbenzidine and 3,3'-dimethoxybenzidine, respectively. ... In vitro anaerobic incubations of rat intestinal microorganisms were evidently able to reduce and cleave the azo bonds of dyes derived from benzidine, 3,3'-dimethylbenzidine and 3,3'-dimethoxybenzidine to form potentially carcinogenic aromatic amines.
Cerniglia CE et al; Carcinogenesis 3 (11): 1255-60 (1982)
Direct Red 2 was /admin/ as an aqueous soln to rats and hamsters to determine whether the dye is cleaved to potentially carcinogenic aromatic amines. ... Assays of the urine from treated animals by EC/GC (electron capture gas chromatography) revealed appreciable levels of 3,3'-dimethylbenzidine, mono- and di-acetyldimethylbenzidine, and alkaline hydrolyzable conjugates. Peak concn of the metabolites in the urine occurred 12-24 hr after admin to rats, and within 12 hr in hamsters. The levels of all metabolites and conjugates diminished rapidly in both species after peak concn were reached, with no residues detected after 96 hr. The results ... demonstrated in vivo cleavage of the dye in both species. ...
Nony CR et al; J Anal Toxicol 7 (1): 49-54 (1983)

7.3 Transformations

8 Use and Manufacturing

8.1 Uses

Sources/Uses
Used as dye (chromed leather, cotton, wool, viscose rayon, silk, nylon, linen, paper, cellulose, and jute), analytical reagent (detection of aluminum, magnesium, mercury, silver, and uranium), biological stain, and pH indicator; [HSDB]
Industrial Processes with risk of exposure
FOR DYEING PRIMARILY COTTON & VISCOSE RAYON; AS ANALYTICAL REAGENT IN DETECTION OF ALUMINUM & MAGNESIUM; AS ANALYTICAL REAGENT IN DETECTION OF MERCURY, SILVER & URANIUM; AS A BIOLOGICAL STAIN; AS A PH INDICATOR
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 185
Dye (polyamide)
Ashford, R.D. Ashford's Dictionary of Industrial Chemicals. London, England: Wavelength Publications Ltd., 1994., p. 357
Dye chromed leather, cotton, wool, silk, nylon, linen, beater paper and jute and to print cellulose, wool and nylon. However, its lightfastness is poor.
Green FJ; The Sigma-Aldrich Handbook of Stains, Dyes and Indicators. Milwaukee, WI: Aldrich Chemical Company, Inc. p. 135 (1990)

8.2 Methods of Manufacturing

PREPD FROM DIAZOTIZED O-TOLIDINE & SODIUM 4-AMINO-1-NAPHTHALENESULFONATE: GERMAN PATENT 35,615 (1885 TO AG FUR ANILINFABRIKATION BERLIN)...
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 185
C.I. Direct Red 2 is made by coupling one mole of tetraazotized o-tolidine with two moles of naphthionic acid (a pH of 8-10 is maintained during coupling).
Green FJ; The Sigma-Aldrich Handbook of Stains, Dyes and Indicators. Milwaukee, WI: Aldrich Chemical Company, Inc. p. 135 (1990)

8.3 U.S. Production

(1977) 3.68X10+7 GRAMS
SRI
(1979) 3.22X10+7 GRAMS
SRI

8.4 U.S. Imports

(1977) 5.00X10+5 GRAMS (PRINCPL CUSTMS DISTS)
SRI
(1979) 2.00X10+6 GRAMS (PRINCPL CUSTMS DISTS)
SRI

8.5 General Manufacturing Information

EPA TSCA Commercial Activity Status
1-Naphthalenesulfonic acid, 3,3'-[(3,3'-dimethyl[1,1'-biphenyl]-4,4'-diyl)bis(2,1-diazenediyl)]bis[4-amino-, sodium salt (1:2): INACTIVE

9 Identification

9.1 Analytic Laboratory Methods

NIOSH Method 5013. Determination of Dyes, Benzidine-, o-Tolidine-, and o-Dianisidine by High Performance Liquid Chromatography with UV Detection. This method is applicable to air samples. DL= 0.0060 mg/cu m.
USEPA; EMMI. Environmental Monitoring Methods Index. Version 2.0. NTIS PB95-502415 (1995)

9.2 NIOSH Analytical Methods

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

Pictogram(s)
Health Hazard
Signal
Danger
GHS Hazard Statements
H350 (95.1%): May cause cancer [Danger Carcinogenicity]
Precautionary Statement Codes

P203, P280, P318, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 41 reports by companies from 3 notifications to the ECHA C&L Inventory.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

10.1.2 Hazard Classes and Categories

Carc. 1B (95.1%)

10.1.3 Fire Hazards

Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

10.1.4 Hazards Summary

May cause irritation; May cause vomiting and diarrhea after ingestion; [MSDSonline] Metabolic studies have shown that bacteria and mammals can cleave this molecule to form potentially carcinogenic aromatic amines; [HSDB] Dimethylbenzidine-based dyes are reasonably anticipated to be human carcinogens, but neither dogs or rats excreted quantifiable amounts of DMB after being fed C.I. Direct Red 2 or C.I. Direct Red 39; [NTP]

10.2 First Aid Measures

10.2.1 First Aid

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)

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

10.3 Fire Fighting

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

10.4 Accidental Release Measures

10.4.1 Disposal Methods

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.

10.5 Handling and Storage

10.5.1 Nonfire Spill Response

SMALL SPILLS AND LEAKAGE: If you spill this chemical, dampen the solid spill material with 5% ammonium hydroxide, then transfer the dampened material to a suitable container. Use absorbent paper dampened with 5% ammonium hydroxide to pick up any remaining material. Your contaminated clothing and the absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with 5% ammonium hydroxide 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 store this material under ambient temperatures. (NTP, 1992)

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

10.6 Exposure Control and Personal Protection

10.6.1 Personal Protective Equipment (PPE)

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)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

10.7 Stability and Reactivity

10.7.1 Air and Water Reactions

Azo dyes can be explosive when suspended in air at specific concentrations. Insoluble in water.

10.7.2 Reactive Group

Azo, Diazo, Azido, Hydrazine, and Azide Compounds

Non-Redox-Active Inorganic Compounds

Amines, Aromatic

10.7.3 Reactivity Alerts

Explosive

10.7.4 Reactivity Profile

DIRECT RED 2 is an azo compound. Azo, diazo, azido compounds can detonate. This applies in particular to organic azides that have been sensitized by the addition of metal salts or strong acids. Toxic gases are formed by mixing materials of this class with acids, aldehydes, amides, carbamates, cyanides, inorganic fluorides, halogenated organics, isocyanates, ketones, metals, nitrides, peroxides, phenols, epoxides, acyl halides, and strong oxidizing or reducing agents. Flammable gases are formed by mixing materials in this group with alkali metals. Explosive combination can occur with strong oxidizing agents, metal salts, peroxides, and sulfides.

10.8 Regulatory Information

10.8.1 TSCA Requirements

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 1-Naphthalenesulfonic acid, 3,3'-(3,3'-dimethyl(1,1'-biphenyl)-4,4'-diyl)bis(azo))bis(4-amino-, disodium salt is included on this list.
40 CFR 716.120 (7/1/95)

11 Toxicity

11.1 Toxicological Information

11.1.1 Non-Human Toxicity Excerpts

The mutagenic potentials of the azo dyes, direct black 38, direct blue 15 and direct red 2 and their aromatic amine reduction products were tested employing the Ames test and the arabinose resistant assay of Salmonella typhimurium. ...Salmonella typhimurium strains (TA-98) and (SV-50) were used in the mutagenicity tests. All three azo dyes tested were mutagenic in both the Ames and arabinose resistant assays; however the Ames test yielded relatively higher mutagenic responses than the arabinose resistant assay. Relatively higher mutagenic responses were observed with hamster S( than with rat S9 in both assays. Direct black 38 produced higher mutagenic responses in both assays than the other two dyes. The reduction products, benzidine, o-dianisidine and o-tolidine were all mutagenic in the Ames test. In the arabinose resistant assay, benzidine was only weakly mutagenic, and o-dianisidine and o-tolidine were nonmutagenic. ... Both the Ames test and arabinose resistant assay are sensitive in testing the mutagenicity of azo dyes, but the Ames test is more efficient than the arabinose resistant assay in detecting mutagenicity of the aromatic amine reduction products in these dyes.
Krishna G et al; J Toxicol Environ Health 18 (1): 111-19 (1986)
Direct red 2 (C.I. 23500) was evaluated for mutagenicity in the Salmonella/microsome preincubation assay using a standard protocol approved by the National Toxicology Program. Direct red 2 was tested at doses of 0, 100, 333, 1000, 3333, and 10,000 ug/plate in four Salmonella typhimurium strains (TA98, TA100, TA1535, and TA1537) in the presence and absence of Aroclor-induced rat or hamster liver S9. Direct red 2 was negative in these tests and the highest ineffective dose level tested without formation of a precipitate or clearing of the background lawn in any Salmonella tester strain was 333 ug/plate.
Zeiger E et al; Environ Mutagen 9:1-110 (1987)

11.1.2 TSCA Test Submissions

The potential for metabolic cleavage of C. I. Direct Red 2 dye fed orally by gavage to 12 male Fischer 344 rats at a dose level of 16 mg dye in 2 ml water (nominal dose of 100 mg/kg body weight, administered in 2 doses, 2 hrs apart) was determined. Feces and urine collected at 12, 24, 48, 96 and 192 hrs after treatment indicated that appreciable cleavage of the dye with subsequent acetylation of the free amine had occurred. No residues of metabolites were found in samples collected in the 24 hr period prior to treatment or in 4 untreated control rats.
National Center for Toxicological Research; Potential for Metabolic Cleavage of Azo Dyes in the Hamster and Rat. (1981), EPA Document No. 40-8329018, Fiche No. OTS0509899
The potential for metabolic cleavage of C. I. Red 2 dye fed orally to 12 male Syrian golden hamsters at a dose level of 10 mg in 2 ml water (nominal dose level of 100 mg/kg body weight, administered in 2 doses, 2 hrs apart) was determined. Feces and urine were collected at 12, 24, 48, 96 and 192 hrs following treatment. Low levels of metabolites were found in the urine with peak levels observed in the 12 hr samples, and the free amine was found to have been acetylated. The feces were observed to have a red coloration indicating excretion of the dye itself. No metabolites were detected in the 48-192 hr post-treatment period.
National Center for Toxicological Research; Metabolic Cleavage of Azo Dyes in the Hamster and Rat. (1981), EPA Document No. 40-8329018, Fiche No. OTS050899
Acute oral toxicity was evaluated in 5 male and 5 female rats (strain not reported) administered a single dose of benzo purpurine (4 BMP) by oral gavage as a 50% w/v suspension in distilled water at a level of 5.0 g/kg body weight. Mortality was not observed in any animal and the LD50 value was calculated to be greater than 5.0 g/kg. The animals were observed at 1, 2 and 4 hours and daily for 14 days post-dosing and body weights were recorded before dosing and 14 days after dosing. All 10 animals displayed weight gains. Ptosis and chromorhinorrhea were observed in 1 male rat and chromorhinorrhea and red diarrhea were observed in another. Necropsy observations were reported to be normal in all rats.
M B Research Laboratories, Inc.; Acute Oral Toxicity in Rats (1978), EPA Document No. 878211051, Fiche No. OTS0206237-2
Acute dermal toxicity was evaluated in 4 New Zealand White rabbits (2 male and 2 female) receiving a single occluded application of benzo purpurine (4 BMP) at a level of 2.0 g/kg body weight for 24 hours on abraded or unabraded skin. Mortality was not observed in any animal and the LD50 value was calculated to be greater than 2.0 g/kg. Clinical observations included yellow nasal discharge, erythema, edema, lethargy, diarrhea and skin flaking. Necropsy observations included yellow exudate from the mouth and nose and white nodules on the liver.
M B Research Laboratories, Inc.; Acute Dermal Toxicity in Rabbits (1967), EPA Document No. 878212258, Fiche No. OTS0206237-5
Acute inhalation toxicity was evaluated in 5 male and 5 female Sprague-Dawley rats exposed to benzo purpurine (4BMP) at an actual concentration (calculated by averaging the results 5 of gravimetrically obtained samples) of 0.23 + - 0.04 (S.D.) mg/L for 203 minutes. The test atmosphere was generated by a direct dust-feed system. There were no mortalities and an LC50 was not determined. No gross toxic or pharmacological symptoms were observed during exposure or the 14 day post-exposure period and body weight gains were normal. Necropsy observations include microscopic abnormalities of the lungs ranging from nodules and white patches. These were not considered to be treatment related. One animal displayed white patches of tissue on the heart surface.
Southwest Foundation for Research and Education; Evaluation of the Acute Toxicity of Benzo Purpurine 4BMP (100% Conc. Mix No. 70) (TR #78-690) (Code No. 2005 00) in Rats (1979), EPA Document No. 878211052, Fiche No. OTS0206237-2

12 Literature

12.1 Consolidated References

12.2 NLM Curated PubMed Citations

12.3 Springer Nature References

12.4 Chemical Co-Occurrences in Literature

12.5 Chemical-Gene Co-Occurrences in Literature

12.6 Chemical-Disease Co-Occurrences in Literature

13 Patents

13.1 Depositor-Supplied Patent Identifiers

13.2 WIPO PATENTSCOPE

13.3 Chemical Co-Occurrences in Patents

13.4 Chemical-Disease Co-Occurrences in Patents

13.5 Chemical-Gene Co-Occurrences in Patents

14 Biological Test Results

14.1 BioAssay Results

15 Classification

15.1 MeSH Tree

15.2 ChemIDplus

15.3 CAMEO Chemicals

15.4 UN GHS Classification

15.5 NORMAN Suspect List Exchange Classification

15.6 EPA DSSTox Classification

15.7 EPA TSCA and CDR Classification

15.8 EPA Substance Registry Services Tree

15.9 MolGenie Organic Chemistry Ontology

16 Information Sources

  1. CAMEO Chemicals
    LICENSE
    CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data.
    https://cameochemicals.noaa.gov/help/reference/terms_and_conditions.htm?d_f=false
    CAMEO Chemical Reactivity Classification
    https://cameochemicals.noaa.gov/browse/react
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA Chemicals under the TSCA
    1-Naphthalenesulfonic acid, 3,3'-[(3,3'-dimethyl[1,1'-biphenyl]-4,4'-diyl)bis(2,1-diazenediyl)]bis[4-amino-, sodium salt (1:2)
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  4. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
    Disodium 3,3'-((3,3'-dimethyl(1,1'-biphenyl)-4,4'-diyl)bis(azo)bis(4-aminonaphthalene-1-sulphonate)
    https://echa.europa.eu/substance-information/-/substanceinfo/100.012.359
    Disodium 3,3'-((3,3'-dimethyl(1,1'-biphenyl)-4,4'-diyl)bis(azo)bis(4-aminonaphthalene-1-sulphonate) (EC: 213-594-3)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/71121
  6. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  7. Hazardous Substances Data Bank (HSDB)
  8. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
    Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://haz-map.com/About
  9. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  10. Japan Chemical Substance Dictionary (Nikkaji)
  11. NIOSH Manual of Analytical Methods
    LICENSE
    The information provided using CDC Web site is only intended to be general summary information to the public. It is not intended to take the place of either the written law or regulations.
    https://www.cdc.gov/Other/disclaimer.html
  12. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    C.I. Direct Red 2
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  13. Springer Nature
  14. Wikidata
  15. PubChem
  16. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  17. GHS Classification (UNECE)
  18. EPA Substance Registry Services
  19. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  20. PATENTSCOPE (WIPO)
CONTENTS