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439-14-5

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Basic Information
CAS No.: 439-14-5
Name: Diazepam
Article Data: 104
Cas Database
Molecular Structure:
Molecular Structure of 439-14-5 (Diazepam)
Formula: C16H13ClN2O
Molecular Weight: 284.745
Synonyms: Levium;Lovium;Mandro;Mandrozep;Methyldiazepinone;Methyldiazepinone (pharmaceutical);Morosan;NSC 169897;NSC 77518;Nerozen;Neurolytril;Nivalen;Nixtensyn;Novazam;Ortopsique;Paceum;Pax;Paxate;Paxum;Placidox 5;Pomin;Q-Pam;Quievita;Radizepam;Ro 5-2807;Saromet;Seduxen;Servizepam;Sibazon;Sibazone;Sipam;Solis;Sonacon;Stesolid;Tranquase;Tranquirit;Tranquo-Puren;Tranquo-Tablinen;Umbrium;Unisedil;Valaxona;Valitran;Valium Injectable;Vazen;Vival;Winii;Zepaxid;1-Methyl-5-phenyl-7-chloro-1,3-dihydro-2H-1,4-benzodiazepin-2-one;7-Chloro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one;7-Chloro-1-methyl-2-oxo-5-phenyl-3H-1,4-benzodiazepine;7-Chloro-1-methyl-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one;7-Chloro-1-methyl-5-phenyl-1,3-dihydrobenzo[e][1,4]diazepin-2-one;7-Chloro-1-methyl-5-phenyl-3H-1,4-benzodiazepin-2(1H)-one;Alboral;Aliseum;Alupram;An-Ding;Ansiolin;Ansiolisina;Antenex;Anxionil;Apo-diazepam;Apozepam;Armonil;Assival;Atilen;Azedipamin;Baogin;Bialzepam;Calmocitene;Calmod;Calmpose;Cercine;Ceregulart;Chuansuan;2H-1,4-Benzodiazepin-2-one,7-chloro-1,3-dihydro-1-methyl-5-phenyl-;Diaceplex;Dialag;Dialar;Diastat;Diazem;Diazemuls;Diazepam-Lipuro;Diazepin;Disopam;Ducene;Dupin;Duxen;Elcion CR;Eridan;Euphorin P;Eurosan;Evacalm;Faustan;Gewacalm;Gradual;Horizon(pharmaceutical);Jinpanfan;Kratium;Lamra;
EINECS: 207-122-5
Density: 1.261 g/cm3
Melting Point: 131.5-134.5 °C
Boiling Point: 497.38 °C at 760 mmHg
Flash Point: 254.607 °C
Solubility: 50mg/L(25 oC)
Appearance: Light yellow crystalline solid
Hazard Symbols: HarmfulXn, ToxicT, FlammableF, IrritantXi
Risk Codes: 21/22-39/23/24/25-23/24/25-11-36/37/38
Safety: 36/37-45-36-26
Transport Information: UN 2811 6.1/PG 3
PSA: 32.67000
LogP: 2.65440
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Chemistry


IUPAC Name: 7-chloro-1-methyl-5-phenyl-3H-1,4-benzodiazepin-2-one
Molecular Formula: C16H13ClN2O
Molecular Weight: 284.74 g/mol
EINECS: 207-122-5
Product Categories: Miscellaneous Biochemicals; Aromatics; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals; Benzodiazepin Analoga StructureAlphabetic; DIA - DICForensic and Veterinary Standards; Chemical Structure; D; Drugs of Abuse; Drugs&Metabolites; Solutions
storage temp.: 2-8 °C
solubility: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 1.6 mg/mL
Stability: Stable. Light-sensitive. Incompatible with strong oxidizing agents.
Melting Point: 131.5-134.5 °C
Index of Refraction: 1.635
Molar Refractivity: 80.91 cm3
Molar Volume: 225.8 cm3
Surface Tension: 46.1 dyne/cm
Density: 1.26 g/cm3
Flash Point: 254.6 °C
Enthalpy of Vaporization: 76.53 kJ/mol
Boiling Point: 497.4 °C at 760 mmHg
Vapour Pressure of Diazepam (CAS NO.439-14-5): 4.98E-10 mmHg at 25 °C

History

 Diazepam was the second benzodiazepine to be invented by Sternbach of Hoffmann-La Roche, and was approved for use in 1960. In 1963 its improved version, Valium, was released and was incredibly popular, helping Roche to become a pharmaceutical industry giant.  Diazepam was the top-selling pharmaceutical in the United States from 1969 to 1982, with peak sales in 1978 of 2.3 billion tablets. Diazepam - along with oxazepam, nitrazepam, and temazepam - represents 82% of the benzodiazepine market in Australia. It is also the first line of defense for a rare disorder called stiff-person syndrome.

Uses

 Diazepam (CAS NO.439-14-5) is mainly used to treat anxiety, insomnia, and symptoms of acute alcohol or opiate withdrawal. It is also used as a premedication for inducing sedation, anxiolysis or amnesia before certain medical procedures (e.g., endoscopy). It is also used as a short-term sedative and anxiolytic for cats and dogs. It is also used for short-term treatment of seizures in dogs and short-term and long-term treatment of seizures in cats. It can also be used as an appetite stimulant.

Production

Diazepam(439-14-5) is a substituted benzodiazepine made by a series of reactions, one of which involves cyclization.
 It is prepared by treating p-chloromethylaniline with benzoyl chloride and hydroxylamine to produce the benzophenone oxime. Reaction of the oxime with chloroacetyl chloride in the presence of sodium hydroxide, and subsequent reduction, yields Diazepam.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 parenteral > 800mg/kg (800mg/kg)   Drugs in Japan Vol. -, Pg. 500, 1995.
infant TDLo intravenous 150ug/kg (0.15mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" British Medical Journal. Vol. 2, Pg. 298, 1977.
mammal (species unspecified) LD50 oral 500mg/kg (500mg/kg)   Doklady Akademii Nauk SSSR. Proceedings of the Academy of Sciences of the USSR. For English translation, see DBIOAM and DKBSAS. Vol. 320, Pg. 242, 1991.
mammal (species unspecified) LD50 unreported 110mg/kg (110mg/kg)   Pharmaceutical Chemistry Journal Vol. 25, Pg. 193, 1991.
man TDLo intravenous 71ug/kg/1M-C (0.071mg/kg) VASCULAR: OTHER CHANGES Drug Intelligence and Clinical Pharmacy. Vol. 17, Pg. 125, 1983.
man TDLo intravenous 143ug/kg (0.143mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
JAMA, Journal of the American Medical Association. Vol. 238, Pg. 1052, 1977.
man TDLo oral 143ug/kg (0.143mg/kg) SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE

SENSE ORGANS AND SPECIAL SENSES: DIPLOPIA: EYE
British Journal of Clinical Pharmacology. Vol. 1, Pg. 335, 1974.
mouse LD50 intramuscular 65mg/kg (65mg/kg)   European Journal of Pharmacology. Vol. 13, Pg. 150, 1971.
mouse LD50 intraperitoneal 37mg/kg (37mg/kg)   Strahlentherapie. Vol. 127, Pg. 245, 1965.
mouse LD50 intravenous 25mg/kg (25mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 31, Pg. 2180, 1981.
mouse LD50 oral 48mg/kg (48mg/kg)   Pharmaceutical Chemistry Journal Vol. 17, Pg. 30, 1983.
mouse LD50 parenteral 80mg/kg (80mg/kg)   United States Patent Document. Vol. #4371536,
mouse LD50 rectal 500mg/kg (500mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 34, Pg. 2226, 1992.
mouse LD50 skin 800mg/kg (800mg/kg)   Anesteziologiya i Reanimatologiya. Vol. (4), Pg. 57, 1980.
mouse LD50 subcutaneous 800mg/kg (800mg/kg)   United States Patent Document. Vol. #3966793,
mouse LD50 unreported 140mg/kg (140mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: ATAXIA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Pharmaceutical Chemistry Journal Vol. 18, Pg. 266, 1984.
rabbit LD50 intravenous 9mg/kg (9mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

BEHAVIORAL: REGIDITY

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
International Journal of Neuropharmacology. Vol. 5, Pg. 305, 1966.
rabbit LD50 oral 328mg/kg (328mg/kg)   Current Therapeutic Research, Clinical & Experimental. Vol. 7, Pg. 590, 1965.
rat LD50 intraperitoneal 46500ug/kg (46.5mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 23, Pg. 682, 1992.
rat LD50 intravenous 32mg/kg (32mg/kg)   Current Therapeutic Research, Clinical & Experimental. Vol. 7, Pg. 590, 1965.
rat LD50 oral 249mg/kg (249mg/kg)   Drugs in Japan Vol. -, Pg. 500, 1995.
rat LD50 parenteral 131mg/kg (131mg/kg)   Drugs in Japan Vol. -, Pg. 500, 1995.
rat LD50 rectal 600mg/kg (600mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 34, Pg. 2226, 1992.
rat LD50 subcutaneous 6350ug/kg (6.35mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 23, Pg. 682, 1992.
women TDLo intramuscular 181ug/kg (0.181mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

CARDIAC: CHANGE IN RATE
British Medical Journal. Vol. 1, Pg. 144, 1977.
women TDLo oral 5mg/kg (5mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) British Journal of Obstetrics and Gynaecology. Vol. 100, Pg. 185, 1993.

Consensus Reports

Diazapam is reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Safety Profile

Hazard Codes: HarmfulXn,IrritantXi,ToxicT,Flammable
Risk Statements: 21/22-39/23/24/25-23/24/25-11-36/37/38
R21/22:  Harmful in contact with skin and if swallowed 
R39/23/24/25:  Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed 
R23/24/25:  Toxic by inhalation, in contact with skin and if swallowed 
R11:  Highly Flammable 
R36/37/38:  Irritating to eyes, respiratory system and skin
Safety Statements: 36/37-45-36-26
S36/37:  Wear suitable protective clothing and gloves 
S45:  In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) 
S36:  Wear suitable protective clothing 
S26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
RIDADR:  UN 2811 6.1/PG 3
WGK Germany:  2
RTECS: DF1575000
HazardClass: 6.1(b)
PackingGroup: III
Poison by ingestion, parenteral, subcutaneous, intravenous, and intraperitoneal routes. Moderately toxic by skin contact.  Human reproductive effects by ingestion and intravenous routes causing developmental abnormalities of the fetal cardiovascular (circulatory) system and postnatal effects. Experimental teratogenic and reproductive effects. Human mutation data reported. An allergen. A drug for the treatment of anxiety. When heated to decomposition it emits very toxic fumes of Cl and NOx.

Specification

  Diazepam (CAS NO.439-14-5), its Synonyms are 1-Methyl-5-phenyl-7-chloro-1,3-dihydro-2H-1,4-benzodiazepin-2-one ; 2H-1,4-Benzodiazepin-2-one, 7-chloro-1,3-dihydro-1-methyl-5-phenyl- ; 7-Chloro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one ; 7-Chloro-1-methyl-2-oxo-5-phenyl-3H-1,4-benzodiazepine ; 7-Chloro-1-methyl-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one ; 7-Chloro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one ; 7-Chloro-1-methyl-5-phenyl-3H-1,4-benzodiazepin-2(1H)-one ; Atensine ; Atilen ; Azedipamin ; Diazepam Stada ; Diazepam intensol ; Diazepam-Eurogenerics . It is off-white to yellow crystalline powder.