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54-85-3

Basic Information
CAS No.: 54-85-3
Name: Isoniazid
Molecular Structure:
Molecular Structure of 54-85-3 (Isoniazid)
Formula: C6H7N3O
Molecular Weight: 137.14
Synonyms: Isonicotinicacid hydrazide (8CI);4-(Hydrazinocarbonyl)pyridine;4-Pyridinecarboxylic acid hydrazide;Mayambutol;Neoteben;Niplen;Pelazid;Pycazide;Pyridine-4-carbohydrazide;Raumanon;Rimicid;Rimiphone;Teebaconin;Zinadon;
EINECS: 200-214-6
Density: 1.244 g/cm3
Melting Point: 171-173 °C(lit.)
Boiling Point: 251.97°C (rough estimate)
Flash Point: >250°C
Solubility: 14 g/100 mL (25 °C) in water
Appearance: white crystalline powder
Hazard Symbols: HarmfulXn
Risk Codes: 22-40-36/37/38
Safety: 36/37/39-26
Transport Information: UN 2811
PSA: 68.01000
LogP: 0.77630
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History

Isoniazid  was first synthesised in the early 20th century, but its activity against tuberculosis was first reported in the early 1950's and three pharmaceutical companies attempted unsuccessfully to simultaneously patent the drug (most prominently, Roche, who launched their version, Rimifon, in 1952). With the introduction of isoniazid, a cure for tuberculosis was first considered reasonable.

Consensus Reports

IARC Cancer Review: Group 3 IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 , 1987,p. 227.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) , Animal Sufficient Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 4 , 1974,p. 159.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . EPA Genetic Toxicology Program.

Specification

The Isonicotinic acid hydrazide with CAS registry number of 54-85-3 is also called 4-Pyridinecarbonylhydrazine. Its EINECS registry number is 200-214-6. The IUPAC name is pyridine-4-carbohydrazide. In addition, the molecular formula is C6H7N3O and the molecular weight is 137.14. It is a kind of white crystalline powder and belongs to the class of Amide. And it is stable and incompatible with strong oxidizing agents, chloral, aldehydes, iodine, ferric salts and hypochlorites.

Physical properties about this chemical are: (1)ACD/LogP: -0.89; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.89; (4)ACD/LogD (pH 7.4): -0.89; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 7.77; (8)ACD/KOC (pH 7.4): 7.84; (9)#H bond acceptors: 4; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 36.44 Å2; (13)Index of Refraction: 1.583; (14)Molar Refractivity: 36.86 cm3; (15)Molar Volume: 110.1 cm3; (16)Polarizability: 14.61 ×10-24cm3; (17)Surface Tension: 57.8 dyne/cm; (18)Density: 1.244 g/cm3.

Preparation of Isonicotinic acid hydrazide: it can be prepared by isonicotinic acid and hydratehydrazine through condensation reaction. The reaction time is 3 hours at reaction temperature of 129-130 °C. After a series of decoloring by activated carbon, filtration, cooling and crystallization you can get the crude. Then you can go through the operation of recrystallization, filtering, drying to get the products. The yield is about 90%.

Uses of Isonicotinic acid hydrazide: it can be used for electroplating additives and pharmaceutical intermediates. It remains the treatment of choice for tuberculosis. And it can react with pyridine-4-carbaldehyde to get pyridine-4-carbaldehyde isonicotinoylhydrazone. This reaction will need reagent conc.HCl and solvent ethanol. The reaction time is 30 minutes at reaction temperature of 20 °C. The yield is about 90%.

Isonicotinic acid hydrazide can react with pyridine-4-carbaldehyde to get pyridine-4-carbaldehyde isonicotinoylhydrazone

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful if swallowed and irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(NN)c1ccncc1
(2)InChI: InChI=1/C6H7N3O/c7-9-6(10)5-1-3-8-4-2-5/h1-4H,7H2,(H,9,10)
(3)InChIKey: QRXWMOHMRWLFEY-UHFFFAOYAD

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 intraperitoneal 325mg/kg (325mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Klinische Wochenscrift. Vol. 30, Pg. 959, 1952.
child TDLo oral 125mg/kg (125mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: COMA
Annals of Emergency Medicine. Vol. 17, Pg. 73, 1988.
child TDLo oral 195mg/kg (195mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: HEADACHE
Japanese Journal of Toxicology. Vol. 12, Pg. 225, 1999.
child TDLo oral 3600mg/kg/43W (3600mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

BEHAVIORAL: ATAXIA

BEHAVIORAL: TREMOR
Canadian Medical Association Journal. Vol. 148, Pg. 49, 1993.
dog LD50 oral 50mg/kg (50mg/kg)   American Review of Tuberculosis. Vol. 65, Pg. 392, 1952.
guinea pig LD50 intramuscular 255mg/kg (255mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA
Schweizerische Zeitschrift fuer Tuberkulose und Pneumonologie. Vol. 9, Pg. 226, 1952.
guinea pig LD50 intraperitoneal 195mg/kg (195mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Klinische Wochenscrift. Vol. 30, Pg. 959, 1952.
guinea pig LD50 intravenous 220mg/kg (220mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Archiv fuer Toxikologie. Vol. 22, Pg. 80, 1966.
guinea pig LD50 oral 255mg/kg (255mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA
Schweizerische Zeitschrift fuer Tuberkulose und Pneumonologie. Vol. 9, Pg. 226, 1952.
guinea pig LD50 subcutaneous 195mg/kg (195mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA
Schweizerische Zeitschrift fuer Tuberkulose und Pneumonologie. Vol. 9, Pg. 226, 1952.
human LDLo oral 100mg/kg (100mg/kg) PERIPHERAL NERVE AND SENSATION: STRUCTURAL CHANGE IN NERVE OR SHEATH American Review of Respiratory Disease. Vol. 105, Pg. 206, 1972.
infant TDLo oral 91mg/kg (91mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Pediatrics. Vol. 95, Pg. 700, 1995.
man LDLo oral 116mg/kg (116mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

CARDIAC: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: EMPHYSEMA
Journal of Analytical Toxicology. Vol. 16, Pg. 57, 1992.
man LDLo oral 523mg/kg/17W- (523mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE"

LIVER: "HEPATITIS, FIBROUS (CIRRHOSIS, POST-NECROTIC SCARRING)"
JAMA, Journal of the American Medical Association. Vol. 176, Pg. 877, 1961.
man TDLo oral 39mg/kg/9D-I (39mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" Southern Medical Journal. Vol. 75, Pg. 81, 1982.
man TDLo oral 100mg/kg/3W-C (100mg/kg) BEHAVIORAL: ANOREXIA (HUMAN

SKIN AND APPENDAGES (SKIN): SWEATING: OTHER

KIDNEY, URETER, AND BLADDER: OTHER CHANGES
American Review of Respiratory Disease. Vol. 106, Pg. 849, 1972.
man TDLo oral 430mg/kg (430mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Neurology. Vol. 20, Pg. 299, 1970.
mouse LD50 intramuscular 137mg/kg (137mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
American Review of Tuberculosis. Vol. 65, Pg. 376, 1952.
mouse LD50 intraperitoneal 100mg/kg (100mg/kg)   National Technical Information Service. Vol. AD277-689,
mouse LD50 intravenous 149mg/kg (149mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Journal of Pharmacology and Experimental Therapeutics. Vol. 122, Pg. 110, 1958.
mouse LD50 oral 133mg/kg (133mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
American Review of Tuberculosis. Vol. 65, Pg. 376, 1952.
mouse LD50 subcutaneous 125mg/kg (125mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Yakugaku Zasshi. Journal of Pharmacy. Vol. 81, Pg. 1225, 1961.
rabbit LD50 intracrebral > 12mg/kg (12mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA
Schweizerische Zeitschrift fuer Tuberkulose und Pneumonologie. Vol. 9, Pg. 226, 1952.
rabbit LD50 intramuscular 155mg/kg (155mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA
Schweizerische Zeitschrift fuer Tuberkulose und Pneumonologie. Vol. 9, Pg. 226, 1952.
rabbit LD50 intraperitoneal 147mg/kg (147mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA
Schweizerische Zeitschrift fuer Tuberkulose und Pneumonologie. Vol. 9, Pg. 226, 1952.
rabbit LD50 intravenous 94mg/kg (94mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD American Review of Tuberculosis. Vol. 65, Pg. 376, 1952.
rabbit LD50 oral 250mg/kg (250mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 12, Pg. 22, 1962.
rabbit LD50 subcutaneous 135mg/kg (135mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA
Schweizerische Zeitschrift fuer Tuberkulose und Pneumonologie. Vol. 9, Pg. 226, 1952.
rat LD50 intramuscular 400mg/kg (400mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Therapie. Vol. 8, Pg. 62, 1953.
rat LD50 intraperitoneal 335mg/kg (335mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA
Schweizerische Zeitschrift fuer Tuberkulose und Pneumonologie. Vol. 9, Pg. 226, 1952.
rat LD50 intravenous 365mg/kg (365mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 26, Pg. 409, 1976.
rat LD50 oral 1250mg/kg (1250mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 26, Pg. 409, 1976.
rat LD50 subcutaneous 329mg/kg (329mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 119, Pg. 444, 1957.
women TDLo oral 12mg/kg/2D-I (12mg/kg) BEHAVIORAL: TOXIC PSYCHOSIS

BEHAVIORAL: ATAXIA
Neurology. Vol. 34, Pg. 703, 1984.
women TDLo oral 90200ug/kg/7D (90.2mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: HEADACHE

CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE
Pediatrics. Vol. 97, Pg. 782, 1996.
women TDLo oral 99300ug/kg (99.3mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

GASTROINTESTINAL: NAUSEA OR VOMITING
Pediatrics. Vol. 95, Pg. 700, 1995.
women TDLo oral 11250mg/kg (11250mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: COMA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Anaesthesia. Vol. 47, Pg. 781, 1992.

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