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カルブロマール

Hoggar

HCID 6488
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
77-65-6
標準SMILES
CCC(Br)(CC)C(=O)NC(N)=O
InChIKey
OPNPQXLQERQBBV-UHFFFAOYSA-N
分子式
C7H13BrN2O2
平均分子量
237.09 g/mol
単同位体質量
236.01604

概要

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

名称と識別子

優先名称
Hoggar
IUPAC
2-bromo-N-carbamoyl-2-ethylbutanamide
現地名
カルブロマール
英語名
(2-Bromo-2-ethylbutyryl)urea
分子式
C7H13BrN2O2
分子量
237.09

名称と別名

CARBROMAL77-65-6AdalinHoggarBromadelCarbromalumButanamide, N-(aminocarbonyl)-2-bromo-2-ethyl-2-Bromo-2-ethylbutyrylureaDTXSID80202522-bromo-2-ethylbutyryureaNSC-491910Y299JY9V3
名称をさらに表示
アダリンチルジンアジソムノールウラダールカルブロマールブロマダールニクタールN-(アミノカルボニル)-2-ブロモ-2-エチルブタンアミドプラナダリンジアシドNictalNYCTALURADALTILDINFydalinKartrylNenesin
DTXCID80252(2-bromo-2-ethylbutanoyl)ureaRefChem:123685N05CM04201-046-6BromadalDiacid2-bromo-N-carbamoyl-2-ethylbutanamide

データベース識別子

CAS
77-65-6
PubChem CID
6488
DTXSID
DTXSID8020252
ChEMBL
CHEMBL1697828
ChEBI

物性

構造計算による物性

XLogP
1.5
極性表面積
72.2 Ų
水素結合供与体数
2
水素結合受容体数
2
回転可能結合数
3
重原子数
12
形式電荷
0
複雑度
190

実験および物理化学的性質

DrugsDEA NFLIS-Drug Category -> Depressants and Tranquilizers
LogP1.54
OdorODORLESS
TasteTASTELESS
Density · 2 件

1.544 at 77 °F (NTP, 1992) - Denser than water; will sink

1.544 @ 25 °C

Color/Form · 3 件

WHITE, CRYSTALLINE POWDER

CRYSTALS

RHOMBIC CRYSTALS FROM DIL ALCOHOL

Solubility · 3 件

less than 1 mg/mL at 72 °F (NTP, 1992)

1 G DISSOLVES IN ABOUT 3000 ML WATER, 18 ML ALCOHOL, 3 ML CHLOROFORM, 14 ML ETHER; VERY SOL IN BOILING ALCOHOL; DISSOLVES IN CONCN SULFURIC, NITRIC & HCL ACIDS; DISSOLVED BY SOLN OF ALKALI HYDROXIDES

SOL IN ACETONE & BENZENE

Human DrugsPharmaceuticals
Melting Point · 2 件

244 °F (NTP, 1992)

116-119 °C

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

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 4 件

Danger

H301 (50%): Toxic if swallowed [Danger Acute toxicity, oral]

P264, P270, P301+P316, P301+P317, P321, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory InformationButanamide, N-(aminocarbonyl)-2-bromo-2-ethyl-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Other Safety InformationIMAP assessments - Butanamide, N-(aminocarbonyl)-2-bromo-2-ethyl-: Human health tier I assessment
Fire HazardsFlash point data for this compound are not available; however, it is probably combustible. (NTP, 1992)
Health Hazards · 1 件

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.

Reactive GroupAmides and Imides
Special ReportsDHEW/NCI; Bioassay of Carbromal for Possible Carcinogenicity (1979) Technical Rpt Series No. 173 DHEW Pub No. (NIH) 79-1729
Reactivity ProfileThe neat material may be sensitive to prolonged exposure to air and light. This chemical is incompatible with acids and alkalis. (NTP, 1992)

化学と産業

薬理情報

ATC Code · 2 件

N - Nervous system

QN - Nervous system

Mechanism of ActionPARTIALLY DECOMP TO BROMIDE ION, BUT SEDATIVE ACTION IS PRESUMABLY DUE TO INTACT MOLECULE.
Metabolism/Metabolites · 5 件

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.

Absorption, Distribution and Excretion · 5 件

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.

用途と製造

UsesMEDICATION

関連反応

0 件
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現在のフィルター条件では反応記録がありません。

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
CHEBI:134961
UNII
0Y299JY9V3
EC Number
201-046-6
Nikkaji
J4.210B
Collision Cross Section139.8 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
Other Experimental PropertiesDISSOLVES IN CONCN SULFURIC, NITRIC & HYDROCHLORIC ACIDS FROM WHICH IT IS PPT ON DILUTION WITH WATER

物理化学的性質

融点
116 · 116-119°
比重(密度)
1.5528 · 1.5528 (rough estimate)
屈折率
1.514 · 1.5140 (estimate)
水溶解度
0.5 g/L · 0.5g/L(20℃)
安定性
安定。可燃性。酸、アルカリ、強酸化剤とは相容れない。
EPAの化学物質情報
Carbromal (77-65-6)

化学的性質

化学的特性white crystalline powder

Air and Water Reactions
May be sensitive to prolonged exposure to air and light. Insoluble in water.
Hazard Classes and CategoriesAcute Tox. 3 (50%)

安全と保護具

Fire FightingFires involving this compound may be controlled using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 件

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.

Nonfire Spill Response · 1 件

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.

Personal Protective Equipment (PPE) · 1 件

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)

毒性情報

Ongoing Test Status · 1 件

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=77-65-6]

Human Toxicity Excerpts · 5 件

...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.

Carcinogen Classification · 6 件

Carbromal

TR-173: Bioassay of Carbromal for Possible Carcinogenicity (CASRN 77-65-6) (1979 )

08/31/78

No Evidence

No Evidence

No Evidence

Non-Human Toxicity Excerpts · 3 件

CARBROMAL ADDED TO RAT OR GUINEA PIG ATRIAL PREPN OR GUINEA PIG LANGENDORFF PREPARATIONS HAD NEGATIVE INOTROPIC, CHRONOTROPIC, DROMOTROPIC, & BATHMOTROPIC EFFECTS.

A STUDY OF BLOOD GASES AND LUNG MORPHOLOGY IN BROMOCARBAMIDE INTOXICATION.

... 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.

Antidote and Emergency Treatment · 4 件

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.

National Toxicology Program Studies · 1 件

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.

安全データ

tsca
TSCA listed
毒性
LD50 oral in rat: 316mg/kg
有毒物質データの
77-65-6(Hazardous Substances Data)
U.S. Exports · 2 件

(1977) No Data

(1979) No Data

U.S. Imports · 2 件

(1977) No Data

(1979) No Data

U.S. Production · 2 件

(1977) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1979) PROBABLY GREATER THAN 4.54X10+5 GRAMS

Consumption PatternsESSENTIALLY 100% AS A CENTRAL DEPRESSANT
Methods of Manufacturing · 2 件

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.

Formulations/PreparationsCARBRITAL (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.
Use ClassificationPharmaceuticals
General Manufacturing Information · 2 件

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).

応用分野

解説アダリン,(Adalin) ブロムジエチルアセチル尿素の商標名。微苦味を有する白色無臭の結晶性粉末。睡眠薬。鎮静剤。※古川ロッパ日記‐昭和九年(1934)三月一九日「ゆふべアダリン四錠のんだのでまだフラフラ」

一般的な説明Odorless tasteless white crystalline powder. Saturated solution in water neutral to litmus.

上流・下流製品情報

上流原料

2-ブロモ-2-エチル酪酸ブロミドN-(アミノカルボニル)-2-エチルブタンアミドButanoic acid, 2-[[(aminocarbonyl)amino]carbonyl]-2-ethyl-カルバミルクロリドメタノールシアン酸

下流製品

(Z)-N-(アミノカルボニル)-2-エチル-2-ブテンアミド

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