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Hoggar

Hoggar structure

Hoggar 

structure
  • CAS No:

    77-65-6

  • Formula:

    C7H13BrN2O2

  • Chemical Name:

    Hoggar

  • Synonyms:

    Butanamide,N-(aminocarbonyl)-2-bromo-2-ethyl-;Carbromal;Urea,(2-bromo-2-ethylbutyryl)-;N-(Aminocarbonyl)-2-bromo-2-ethylbutanamide;Adalin;Bromadal;Bromdiethylacetylurea;Bromodiethylacetylcarbamide;(α-Bromo-α-ethylbutyryl)carbamide;(α-Bromo-α-ethylbutyryl)urea;Kartryl;Nenesin;Nyctal;Planadalin;Tildin;Uradal;2-Bromo-2-ethylbutyrylurea;Hoggar;Karbromal;Pelidorm;α-Ethyl-α-bromobutyrylurea;Parkosed;Diacid;Dormiturin;Bromacetocarbamide;Adisomnol;NSC 49191;NSC 9916;2-Bromo-N-carbamoyl-2-ethylbutanamide

  • Categories:

    Active Pharmaceutical Ingredients  >  Nervous System Drugs

Description

white crystalline powder


Alpha-bromo-alpha-ethylbutyrylurea is an odorless tasteless white crystalline powder. Saturated solution in water neutral to litmus. (NTP, 1992)


Alpha-bromo-alpha-ethylbutyrylurea is an odorless tasteless white crystalline powder. Saturated solution in water neutral to litmus. (NTP, 1992)|Carbromal is a N-acylurea.

Hoggar Basic Attributes

237.09

237.09

201-046-6

0Y299JY9V3

49191|9916

DTXSID8020252

WHITE, CRYSTALLINE POWDER|CRYSTALS|RHOMBIC CRYSTALS FROM DIL ALCOHOL

N - Nervous system

2924210090

Characteristics

72.2

2.22620

Alpha-bromo-alpha-ethylbutyrylurea is an odorless tasteless white crystalline powder. Saturated solution in water neutral to litmus. (NTP, 1992)

1.544 g/cm3 @ Temp: 25 °C

116-119 °C

154-159 °C @ Press: 13 Torr

1.513

SOL IN ACETONE & BENZENE

Peritoneal-rat LD50: 427 mg/kg; oral-mouse LD50: 464 mg/kg

Thermal decomposition to emit toxic nitrogen oxides and bromide fumes

ODORLESS

TASTELESS

139.8 Ų [M+H]+ [CCS Type: TW, Method: Major Mix IMS/Tof Calibration Kit (Waters)]

DISSOLVES IN CONCN SULFURIC, NITRIC & HYDROCHLORIC ACIDS FROM WHICH IT IS PPT ON DILUTION WITH WATER

May be sensitive to prolonged exposure to air and light. Insoluble in water.

Amides and Imides

The neat material may be sensitive to prolonged exposure to air and light. This chemical is incompatible with acids and alkalis. (NTP, 1992)

Safety Information

Treasury is ventilated, low temperature and dry; stored separately from food materials

Stable. Combustible. Incompatible with acids, alkalies, strong oxidizing agents.

P264, P270, P301+P312, P330, P501

H302

DHEW/NCI; Bioassay of Carbromal for Possible Carcinogenicity (1979) Technical Rpt Series No. 173 DHEW Pub No. (NIH) 79-1729

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

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Fires involving this compound may be controlled using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone 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 chemical from exposure to light. Keep the container tightly closed under an inert atmosphere, and store under refrigerated temperatures. (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)

Toxicity

highly toxic

A bioassay for the possible carcinogenicity of carbromal was conducted using Fischer 344 rats and B6C3F1 mice. Carbromal was admin in the feed, at either of two concn, to groups of 50 male and 50 female animals of each species with the exception of 49 low dose male mice and high dose female mice. Twenty animals of each sex and species were placed on test as controls. The high and low dietary concn of carbromal were, respectively, 2,500 and 1,250 ppm for rats and 2,500 and 1,250 ppm for mice. The cmpd was admin for 103 wk to rats and 78 wk for mice. The period of cmpd admin was followed by an observation period of 1 wk for rats and 26 wk for mice. ... Under the conditions of this bioassay, dietary admin of carbromal was not carcinogenic in Fischer 344 rats or B6C3F1 mice. ... Levels of Evidence of Carcinogenicity: Male Rats: Negative; Female Rats: Negative; Male Mice: Negative; Female Mice: Negative.

Drug Information

Sedatives, Nonbarbiturate|MONOUREIDES IN GENERAL ARE SHORT-ACTING SEDATIVE-HYPNOTICS WITH LOW THERAPEUTIC INDEX. CONSEQUENTLY, THEY ARE VERY LITTLE USED. /MONOUREIDES/|DOSE: USUAL, ORAL, 500 MG.

CARBROMAL... /IS ONE OF THE/ OBSOLETE MONOUREIDES THAT.../IS/ STILL AVAILABLE.../IT/ RELEASE/S/ BROMIDE.../ION/ & CAN THUS GIVE RISE TO BROMIDE INTOXICATION.|...IT SHOULD BE USED WITH SAME CARE AS OTHER BROMIDE-CONTAINING COMPD. DUE TO ITS FEEBLE CENTRAL DEPRESSANT EFFECTS, ITS ACTION IS OFTEN UNRELIABLE & DISAPPOINTING.|CLINICAL INVESTIGATIONS ON THE CHRONIC INTOXICATION WITH BROMOCARBAMIDES (CARBROMAL AND BROMISOVAL).|A FEW PATIENTS HAVE SHOWN CROSS-REACTIONS TO CARBROMAL, WHICH IS SIMILAR CHEMICALLY, & 1 WITH FIXED DRUG ERUPTION HAS SHOWN CROSS-REACTION TO CARISOPRODOL, A CHEMICALLY RELATED MUSCLE RELAXANT.

4. 4= VERY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 50-500 MG/KG, BETWEEN 1 TEASPOONFUL & 1 OZ FOR 70 KG PERSON (150 LB).

IT IS READILY OXIDIZED TO UREA IN BODY...|BIOTRANSFORMATION OF CARBROMAL...IN DOGS & RODENTS AFFORDED 2-BROMO-2-ETHYL-3-HYDROXYBUTYRYLUREA & 2-ETHYLBUTRYLUREA. HYDROXYLATION OF ACYL RESIDUE PREDOMINATES IN DOGS, & REDUCTIVE DEBROMINATION PREDOMINATES IN RATS, WHEREAS BOTH REACTIONS ARE IMPORTANT TO MICE. /LATTER/...FOUND IN BODY OF POISONED HUMAN SUBJECTS.|...DIFFERENT ANESTHETIC EFFECTS OBSERVED IN.../MICE, DOGS & RATS/ AFTER DOSE OF DRUG CAN BE ACCOUNTED FOR BY DIFFERENCES IN RATES OF METAB & CONSEQUENT DIFFERENCES IN PROPORTIONS OF RESULTING METABOLITES.|BROMINE CONCN IN URINE AFTER INGESTION OF CARBROMAL IS DESCRIBED.|PHARMACOKINETICS OF CARBROMAL IN THE RAT AND IN MAN.

BIOTRANSFORMATION OF CARBROMAL...IN DOGS & RODENTS AFFORDED 2-BROMO-2-ETHYL-3-HYDROXYBUTYRYLUREA & 2-ETHYLBUTRYLUREA. HYDROXYLATION OF ACYL RESIDUE PREDOMINATES IN DOGS, & REDUCTIVE DEBROMINATION PREDOMINATES IN RATS, WHEREAS BOTH REACTIONS ARE IMPORTANT TO MICE. /LATTER/...FOUND IN BODY OF POISONED HUMAN SUBJECTS.|IN MAMMALIAN LIVER...CARBROMAL...IS TRANSFORMED... (OMEGA-1) OXIDATION, WHICH IS SPECIES DEPENDENT, OCCURS IN MICE, BUT NOT IN DOGS OR RATS, WHEREAS REDUCTIVE DEBROMINATION TAKES PLACE IN ALL 3 SPECIES.|...CARBROMAL...HAS BEEN FOUND TO UNDERGO RAPID BIOTRANSFORMATION TO CIS-2-ETHYLCROTONYLUREA IN RABBIT LIVER PREPN.|IT IS READILY OXIDIZED TO UREA IN BODY...|2-BROMO-2- ETHYL-4-HYDROXYBUTYRAMIDE & 2-BROMO-2-ETHYL-4-BUTYROLACTAM WERE ISOLATED FROM THE URINE OF MICE, RATS, & DOGS AFTER APPLICATION OF CARBROMAL. IDENTIFICATION WAS BY MASS, NMR, & IR SPECTROSCOPY.

PARTIALLY DECOMP TO BROMIDE ION, BUT SEDATIVE ACTION IS PRESUMABLY DUE TO INTACT MOLECULE.

SYMPTOMS: Symptoms of exposure to this compound include mental confusion, ataxia, arreflexia, loss of pupillary response, cyanosis and coma. Other symptoms include severe mental depression, irritability, slurred speech and skin eruptions. Rashes may also occur. ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits very toxic fumes of nitrogen oxides and bromine. (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)

CARDIODEPRESSIVE ACTIONS MAY BE IMPORTANT FOR THE COURSE & ENDING OF SEVERE CARBROMAL INTOXICATIONS.|EFFICIENCY OF DIFFERENT DETOXICATION METHODS FOR CARBROMAL INTOXICATIONS EVALUATED ON BASTARD DOGS. HEMOPERFUSION IS MOST EFFECTIVE IN ELIMINATION OF CARBROMAL & HEMODIALYSIS FOR REMOVAL OF BROMIDE. HEMOFILTRATION WAS LEAST EFFECTIVE FOR BOTH & SHOULD NOT BE USED.|EXPTL DOPAMINE ACCELERATED ELIM OF CARBROMAL 3-FOLD OVER THAT OF FORCED DIURESIS BY INCR URINE FLOW & GLOMERULAR FILTRATION RATE. METHOD RECOMMENDED OVER FORCED DIURESIS SINCE HEMODYNAMICS WAS MORE STABLE & ELECTROLYTE BALANCE LESS DISTURBED.|SERUM LEVELS OF CARBROMAL WERE 7-17 TIMES HIGHER IN POISONED PT THAN THOSE AFTER THERAPEUTIC DOSES. HEMODIALYSIS CAN BE USED TO REMOVE CARBROMAL & ITS METABOLITE, ETHYLBUTYLUREA.

...PT /DESCRIBED/ WHO HAD REVERSIBLE REDN OF VISION WITH CENTRAL SCOTOMA & TEMPORAL PALLOR OF OPTIC NERVEHEAD AFTER YR LONG DAILY USE... CASE /ALSO REPORTED/ OF RETROBULBAR NEURITIS WITH HYPEREMIA OF OPTIC NERVEHEAD FROM CHRONIC POISONING, WITH IMPROVEMENT AFTER DRUG WAS STOPPED.|IN INTOXICATION, SHOCK-LUNG & INTRAVASCULAR COAGULATION DEFECT MAY OCCUR.|A CASE OF INTOXICATION WITH 8 G OF CARBROMAL RESULTING IN ACUTE RENAL FAILURE & BILATERAL DEEP VEIN THROMBOSES IS DESCRIBED.|CASE OF CARBROMAL-INDUCED PURPURA IS DESCRIBED & TYPICAL CLINICAL FEATURES ARE PRESENTED.|For more Human Toxicity Excerpts (Complete) data for CARBROMAL (6 total), please visit the HSDB record page.

carbromal

Hoggar Use and Manufacturing

Methods of Manufacturing

DECARBOXYLATION OF DIETHYLMALONIC ACID FOLLOWED BY REACTION WITH THIONYL CHLORIDE AND UREA, AND BROMINATION OF THE RESULTING ACYLUREA; HEATING OF UREA WITH ALPHA-BROMO-ALPHA-ETHYLBUTYRYL BROMIDE|PREPARED BY HEATING UREA (TO APPROX 50 DEG) WITH ALPHA-BROMO-ALPHA-ETHYLBUTYRYL BROMIDE (C2H5)2CBRCOBR, SEE GERMAN PATENT 225,710 (1910); FRDL 10, 1160; CHEM ZENTR 1910, II, 1008.

Production

(1977) PROBABLY GREATER THAN 4.54X10+5 GRAMS|(1979) PROBABLY GREATER THAN 4.54X10+5 GRAMS

ESSENTIALLY 100% AS A CENTRAL DEPRESSANT

CARBRITAL (PARKE, DAVIS): EACH CAPSULE CONTAINS PENTOBARBITAL SODIUM 45 OR 90 MG & CARBROMAL 120 OR 240 MG; EACH 30 ML OF ELIXIR CONTAINS PENTOBARBITAL SODIUM 120 MG & CARBROMAL 360 MG.

Butanamide, N-(aminocarbonyl)-2-bromo-2-ethyl-: INACTIVE|MONOUREIDES (MONOACYL UREAS) ARE COMPD IN WHICH ONLY 1 AMINO GROUP OF UREA IS CONDENSED WITH CARBOXYL GROUP, & INCL SEVERAL WEAK HYPNOTICS (EG, CARBROMAL).

A MODIFIED METHOD FOR DETERMINING BROMOUREIDES IN BIOLOGICAL FLUIDS BY HIGH-PRESSURE LIQUID CHROMATOGRAPHY IS PRESENTED.|BROMOUREIDES DECOMPOSED POST MORTEM BY PUTREFACTION, SO THAT CONDITION OF CADAVER WAS IMPORTANT. BRAIN TISSUE WAS MOST USABLE MATERIAL FOR EXAM, BUT MUSCLE & KIDNEY COULD BE ANALYZED WITH SUCCESS.|FOLLOWING ETHER EXTRACTION, COMPD RE-EXTRACTED INTO SODIUM HYDROXIDE. UV EXTINCTION OF AQ LAYER FOLLOWED @ 232 NM. IT HAS TO BE CORRECTED FOR EFFECTS OF BIOLOGICAL MATERIALS.|COMPOUNDS COLORIMETRICALLY DETERMINED, COLOR DEVELOPMENT WITH FE(CLO4)3, & SPECTROPHOTOMETRIC ANAL @ 498 NM.|TITRATION.

DRUGS WERE DETERMINED IN BLOOD, SERUM, & URINE BY GAS CHROMATOGRAPHY.|TEST FOR BROMINE IS DESCRIBED WHICH CAN BE USED FOR BROMUREIDE INTOXICATION AS WELL AS FOR CASES OF BROMISM.|CLINICAL-TOXICOLOGICAL STUDIES WITH AID OF GAS-CHROMATOGRAPHY-MASS SPECTROMETRY IN PT WITH OVERDOSE OF NERVOLITAN TABLETS. CARBROMAL & ITS METAB, 2-BROMO-2-ETHYLBUTYRAMIDE, 2-BROMO-2-ETHYL-3-HYDROXYBUTYRAMIDE, & 2-ETHYLBUTYRYLUREA IDENTIFIED IN BLOOD|SAMPLES WERE EXTRACTED FROM BLOOD OR URINE. LIMIT OF DETECTION 0.6 MG.

Pharmaceuticals

Computed Properties

Molecular Weight:237.09
XLogP3:1.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:236.01604
Monoisotopic Mass:236.01604
Topological Polar Surface Area:72.2
Heavy Atom Count:12
Complexity:190
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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