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CAS No.: | 136-40-3 |
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Name: | Phenazopyridine hydrochloride |
Molecular Structure: | |
Formula: | C11H11N5.HCl |
Molecular Weight: | 249.703 |
Synonyms: | Phenazopyridine hydrochloride [USAN];2,6-Diamino-3-(phenylazo)pyridine monohydrochloride;Bisteril;Phenyl-idium;Pyridium;Pyrazodine;Azo-Mandelamine;2,6-Pyridinediamine, 3- (phenylazo)-, monohydrochloride;Phenylazo tablets;Urobiotic-250;Urazium;Thiosulfil-A;3-(Phenylazo)-2,6-pyridinediamine, hydrochloride;2,6-Diamino-3-phenylazopyridine hydrochloride;component of Azo Gantrisin;Azo Gantanol;component of Azo-Mandelamine;Azomine;2,6-Pyridinediamine,3-(phenylazo)-,monohydrochloride;Di-Azo;Azodyne; |
EINECS: | 205-243-8 |
Density: | 1.2645 (rough estimate) |
Melting Point: | 139 ºC |
Boiling Point: | 442.3 ºC at 760 mmHg |
Flash Point: | 221.3 ºC |
Solubility: | 0.01-0.1 g/100 mL at 20 ºC in water |
Appearance: | brick-red crystals |
Hazard Symbols: | Xn,C |
Risk Codes: | 22-36/37/38-40-34 |
Safety: | 26-36/37-45-36/37/39-27 |
PSA: | 89.65000 |
LogP: | 4.62580 |
2,6-Diaminopyridine
aniline
3-phenyldiazenylpyridine-2,6-diamine monohydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride; sodium nitrite 1) 10 min, ice-cooled, 2) r. t., 20 min; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With potassium carbonate In water; ethyl acetate at 20℃; for 0.5h; | 92% |
With sodium hydroxide In water |
salicylaldehyde
3-phenyldiazenylpyridine-2,6-diamine monohydrochloride
2-({[6-amino-5-(2-phenyldiazenyl)pyridin-2-yl]imino}methyl)phenol hydrochloride
Conditions | Yield |
---|---|
In ethanol for 2h; | 86% |
3-phenyldiazenylpyridine-2,6-diamine monohydrochloride
5-Nitrosalicylaldehyde
2-({[6-amino-5-(2-phenyldiazenyl)pyridin-2-yl]imino}methyl)-4-nitrophenol hydrochloride
Conditions | Yield |
---|---|
In ethanol for 2h; | 86% |
2-hydroxy-5-methoxybenzaldehyde
3-phenyldiazenylpyridine-2,6-diamine monohydrochloride
2-({[6-amino-5-(2-phenyldiazenyl)pyridin-2-yl]imino}methyl)-4-methoxyphenol hydrochloride
Conditions | Yield |
---|---|
In ethanol for 2h; | 85% |
3-phenyldiazenylpyridine-2,6-diamine monohydrochloride
2-hydroxynaphthalene-1-carbaldehyde
1-({[6-amino-5-(2-phenyldiazenyl)pyridin-2-yl]imino}methyl)-2-naphthol hydrochloride
Conditions | Yield |
---|---|
In ethanol for 2h; | 83% |
Conditions | Yield |
---|---|
In methanol for 12h; UV-irradiation; | A 35% B 15% C 5% D 12% |
Conditions | Yield |
---|---|
With ammonium hydroxide; copper(II) sulfate In water for 6h; Heating; |
3-phenyldiazenylpyridine-2,6-diamine monohydrochloride
C8H5NO2*C11H11N5
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium hydroxide / water 2: ethanol / 24 h / 60 °C View Scheme |
3-phenyldiazenylpyridine-2,6-diamine monohydrochloride
C8H8O3*C11H11N5
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium hydroxide / water 2: ethanol / 24 h / 20 °C View Scheme |
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IUPAC Name: 3-Phenyldiazenylpyridine-2,6-diamine
Molecular Formula: C11H12ClN5
Molecular Weight: 249.70 g/mol
Canonical SMILES: c1(c(nc(N)cc1)N)\N=N/c1ccccc1.Cl
InChI: InChI=1/C11H11N5.ClH/c12-10-7-6-9(11(13)14-10)16-15-8-4-2-1-3-5-8;/h1-7H,(H4,12,13,14);1H/b16-15-;
EINECS: 205-243-8
Classification Code: Analgesic; Drug / Therapeutic Agent; Human Data; Mutation data; Tumor data
Product Categories: Intermediates & Fine Chemicals; Pharmaceuticals
H-Bond Donor: 3
H-Bond Acceptor: 5
Rotatable Bond Count: 2
Tautomer Count: 12
Exact Mass: 249.078123
MonoIsotopic Mass: 249.078123
Topological Polar Surface Area: 89.6
Heavy Atom Count: 17
Complexity: 237
Flash Point: 221.3 °C
Enthalpy of Vaporization: 69.97 kJ/mol
Boiling Point: 442.3 °C at 760 mmHg
Melting Point: 139 °C
Water Solubility: 0.01-0.1 g/100 mL at 20 °C
Vapour Pressure of Phenazopyridine hydrochloride (CAS NO.136-40-3): 5.1E-08 mmHg at 25 °C
Phenazopyridine hydrochloride (CAS NO.136-40-3) is used as a local anesthetic that has been used in urinary tract disorders. Its use is limited by problems with toxicity (primarily blood disorders) and potential carcinogenicity.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
child | TDLo | oral | 35mg/kg (35mg/kg) | VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION KIDNEY, URETER, AND BLADDER: HEMATURIA BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN | American Journal of Diseases of Children. Vol. 117, Pg. 369, 1969. |
child | TDLo | oral | 125mg/kg (125mg/kg) | LUNGS, THORAX, OR RESPIRATION: CYANOSIS BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN BLOOD: OTHER HEMOLYSIS WITH OR WITHOUT ANEMIA | Clinical Pediatrics Vol. 10, Pg. 537, 1971. |
child | TDLo | oral | 400mg/kg (400mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: CYANOSIS | American Journal of Diseases of Children. Vol. 110, Pg. 105, 1965. |
man | TDLo | oral | 86mg/kg/10D-I (86mg/kg) | SPINAL CORD: INFLAMMATORY CHANGES | Annals of Internal Medicine. Vol. 106, Pg. 164, 1987. |
man | TDLo | oral | 114mg/kg (114mg/kg) | GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED | Human Toxicology. Vol. 2, Pg. 539, 1983. |
mouse | LD50 | intravenous | 180mg/kg (180mg/kg) | U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#04014, | |
rat | LD50 | oral | 472mg/kg (472mg/kg) | Toxicology and Applied Pharmacology. Vol. 1, Pg. 42, 1959. | |
rat | LDLo | intraperitoneal | 200mg/kg (200mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA LUNGS, THORAX, OR RESPIRATION: STRUCTURAL OR FUNCTIONAL CHANGE IN TRACHEA OR BRONCHI | Journal of Pharmacology and Experimental Therapeutics. Vol. 51, Pg. 200, 1934. |
women | TDLo | oral | 34mg/kg (34mg/kg) | GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED | Annals of Internal Medicine. Vol. 72, Pg. 89, 1970. |
women | TDLo | oral | 140mg/kg (140mg/kg) | GASTROINTESTINAL: NAUSEA OR VOMITING BLOOD: NORMOCYTIC ANEMIA | Canadian Medical Association Journal. Vol. 91, Pg. 756, 1964. |
Confirmed carcinogen with experimental carcinogenic and tumorigenic data. A poison by intraperitoneal and intravenous routes. Moderately toxic by ingestion. Human systemic effects by ingestion: somnolence, cyanosis, diarrhea, nausea or vomiting, anuria or decreased urine volume, normocytic anemia, methemoglobinemia-carboxyhemoglobinemia, dehydration, changes in blood sodium levels. Mutation data reported. When heated to decomposition it emits very toxic fumes of NOx and HCl.
Hazard Codes: Xn,C
Risk Statements: 22-36/37/38-40-34
R22: Harmful if swallowed.
R36/37/38: Irritating to eyes, respiratory system and skin.
R34: Causes burns.
R40: Limited evidence of a carcinogenic effect.
Safety Statements of Phenazopyridine hydrochloride (CAS NO.136-40-3): 26-36/37-45-36/37/39-27
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37: Wear suitable protective clothing and gloves.
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S27: Take off immediately all contaminated clothing.
Phenazopyridine hydrochloride (CAS NO.136-40-3), its Synonyms are 2,6-Diamino-3-(phenylazo)pyridine monohydrochloride ; 2,6-Diamino-3-phenylazopyridine hydrochloride ; 2,6-Pyridinediamine, 3-(phenylazo)-, monohydrochloride ; 3-(Phenylazo)-2,6-pyridinediamine, hydrochloride ; 3-Phenylazo-2,6-diaminopyridine hydrochloride ; Azo-Standard ; Azodyne ; Azomine ; Azosulfisox ; Bisteril ; Phenazodine ; Phenazopyridine HCl ; Phenazopyridinium chloride ; Phenyl-idium ; Pyridine, 2,6-diamino-3-(phenylazo)-, hydrochloride and so on. It is brick-red crystals.