异戊巴比妥

基本信息
制备方法及用途
物化性质
安全信息
毒理性
结构与计算化学
上游产品
下游产品
表征图谱

异戊巴比妥基本信息

中文名称：: 异戊巴比妥

中文别名：: 异戊巴比妥;
阿米妥;
5-異戊-5-乙巴比妥酸;
5-乙基-5-(3-甲基丁基)-2,4,6-(1H,3H,5H)-嘧啶三酮;
5-乙基-5-(3-甲基丁基)巴比妥酸

英文名称：: Amobarbital

英文别名：: amobarbital;
Talamo;
5-ethyl-5-isopentyl-barbituric acid;
Barbamil;
Amytal;
Eunoctal;
5-ethyl-5-(3-methylbutyl)-1,3-diazinane-2,4,6-trione;
Amobarbitone;
Pentymal;
Isomytal;
Barbamyl;
Amylobarbitone

CAS No.：: 57-43-2

分子式：: C11H18N2O3

分子量：: 226.27

精确分子量：: 226.13200

PSA：: 75.27000

EINECS：: 200-330-7

InChI：: InChI=1/C11H18N2O3/c1-4-11(6-5-7(2)3)8(14)12-10(16)13-9(11)15/h7H,4-6H2,1-3H3,(H2,12,13,14,15,16)

风险术语：: 11-23/24/25-39/23/24/25

分子结构式：

SDS：: 查看

异戊巴比妥制备方法及用途

制备方法

溴异戊烷经缩合、乙基化、环合而得。1.缩合将乙醇钠的乙醇溶液和乙酸乙酯加入干燥的反应罐中,65-70℃回流0.5h,冷至30℃以下,加入丙二酸二乙酯,搅拌1h。滴加溴异戊烷。加毕,45-50℃反应2h,升温至75-78℃,反应6h。回收乙醇至内温达120℃,再减压蒸除残留乙醇。冷至40℃时加水和少量磺化油,搅拌,静置分取酯层,减压蒸馏,收集相对密度为0.9622-0.9632馏分,得α-异戊基丙二酸二乙酯([5398-08-3],沸点240-242℃)。收率为84%。2.乙基化将乙醇钠的乙醇溶液和乙酸乙酯加入干燥的反应罐内,65-70℃回流0.5h,冷至40℃,加入异戊基丙二酸二乙酯,搅拌1h。于30℃加入溴乙烷。加毕,反应5h。升温至75-80℃,反应1h。蒸馏回收乙醇。冷至40℃,加水溶解。静置,分取酯层。减压蒸馏,收集相对密度为0.9532-0.9549馏分得α-乙基-α-异戊基丙二酸二乙酯。收率为87%。3.环合由α-乙基-α-异戊基丙二酸二乙酯和尿素于75-80℃反应0.5h,回收乙醇,活性炭脱色,盐酸酸化,过滤,干燥得产品。环合收率为72-79%。

合成制备方法

溴异戊烷经缩合、乙基化、环合而得。1.缩合将乙醇钠的乙醇溶液和乙酸乙酯加入干燥的反应罐中，65-70℃回流0.5h，冷至30℃以下，加入丙二酸二乙酯，搅拌1h。滴加溴异戊烷。加毕，45-50℃反应2h，升温至75-78℃，反应6h。回收乙醇至内温达120℃，再减压蒸除残留乙醇。冷至40℃时加水和少量磺化油，搅拌，静置分取酯层，减压蒸馏，收集相对密度为0.9622-0.9632馏分，得α-异戊基丙二酸二乙酯（[5398-08-3]，沸点240-242℃）。收率为84%。2.乙基化将乙醇钠的乙醇溶液和乙酸乙酯加入干燥的反应罐内，65-70℃回流0.5h，冷至40℃，加入异戊基丙二酸二乙酯，搅拌1h。于30℃加入溴乙烷。加毕，反应5h。升温至75-80℃，反应1h。蒸馏回收乙醇。冷至40℃，加水溶解。静置，分取酯层。减压蒸馏，收集相对密度为0.9532-0.9549馏分得α-乙基-α-异戊基丙二酸二乙酯。收率为87%。3.环合由α-乙基-α-异戊基丙二酸二乙酯和尿素于75-80℃反应0.5h，回收乙醇，活性炭脱色，盐酸酸化，过滤，干燥得产品。环合收率为72-79%。

用途简介

该品为中效类催眠药。具有镇静、催眠及抗惊厥作用。该品作用效果快而强。由于交易在肝内破坏,因此作用时间也短。久用会产生耐受性和成瘾性。肝肾功能严重不会时忌用或减量慎用。

用途

该品为中效类催眠药。具有镇静、催眠及抗惊厥作用。该品作用效果快而强。由于交易在肝内破坏，因此作用时间也短。久用会产生耐受性和成瘾性。肝肾功能严重不会时忌用或减量慎用。

异戊巴比妥物化性质

外观与性状：: 白色结晶粉末
密度：: 1.069 g/cm3
熔点：: 156-158°C
水溶解性：: <0.1 g/100 mL at 18.5℃
折射率：: 1.4584
存储条件/存储方法：: 库房通风低温干燥
稳定性相关：: 低温干燥下稳定
其它信息：: 1.       性状：白色结晶性粉末。无臭。微有苦味。

2.       密度（g/mL,25/4℃）：未确定

3.       相对蒸汽密度（g/mL,空气=1）：未确定

4.       熔点（ºC）：156～158

5.       沸点（ºC,常压）：未确定

6.       沸点（ºC,5.2kPa）：未确定

7.       折射率：未确定

8.       闪点（ºC）：未确定

9.       比旋光度（º）：未确定

10.    自燃点或引燃温度（ºC）：未确定

11.    蒸气压（kPa,25ºC）：未确定

12.    饱和蒸气压（kPa,60ºC）：未确定

13.    燃烧热（KJ/mol）：未确定

14.    临界温度（ºC）：未确定

15.    临界压力（KPa）：未确定

16.    油水（辛醇/水）分配系数的对数值：未确定

17.    爆炸上限（%,V/V）：未确定

18.    爆炸下限（%,V/V）：未确定

19.    溶解性：易溶于苯，溶于乙醇、氯仿、乙醚、碱溶液和脂肪烃，微溶于水，不溶于石油醚。

异戊巴比妥安全信息

包装等级：: III
风险类别：: 6.1(b)
海关代码：: 2933530014

异戊巴比妥毒理性

CHEMICAL IDENTIFICATION

RTECS NUMBER :: CQ5075000

CHEMICAL NAME :: Barbituric acid, 5-ethyl-5-isopentyl-

CAS REGISTRY NUMBER :: 57-43-2

LAST UPDATED :: 199712

DATA ITEMS CITED :: 19

MOLECULAR FORMULA :: C11-H18-N2-O3

MOLECULAR WEIGHT :: 226.31

WISWESSER LINE NOTATION :: T6VMVMV FHJ F2 F2Y1&1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 250 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 21,719,1971

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 115 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 21,719,1971

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 190 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: AEPPAE Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. (Berlin, Ger.) V.110-253, 1925-66. For publisher information, see NSAPCC. Volume(issue)/page/year: 152,341,1930

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 345 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JACSAT Journal of the American Chemical Society. (American Chemical Soc., Distribution Office Dept. 223, POB 57136, West End Stn., Washington, DC 20037) V.1- 1879- Volume(issue)/page/year: 61,96,1939

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 175 mg/kg

TOXIC EFFECTS :: Behavioral - general anesthetic

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 10,1078,1967

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 212 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 15,688,1965

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 250 mg/kg

TOXIC EFFECTS :: Behavioral - sleep

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 26,371,1926

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 58 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,63,1990

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 100 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PHREA7 Physiological Reviews. (American Physiological Soc., 9650 Rockville Pike, Bethesda, MD 20814) V.1- 1921- Volume(issue)/page/year: 19,472,1939

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 575 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,63,1990

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 90 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 41,465,1931

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 170 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JACSAT Journal of the American Chemical Society. (American Chemical Soc., Distribution Office Dept. 223, POB 57136, West End Stn., Washington, DC 20037) V.1- 1879- Volume(issue)/page/year: 45,243,1923

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 49 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 96,209,1949

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - species unspecified

DOSE/DURATION :: 550 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 42,253,1931 *** REVIEWS *** TOXICOLOGY REVIEW NEURAI Neurology. (Modern Medicine Pub., Inc., 1 E. First St., Duluth, MN 55802) V.1- 1951- Volume(issue)/page/year: 3,58,1953 TOXICOLOGY REVIEW PHREA7 Physiological Reviews. (American Physiological Soc., 9650 Rockville Pike, Bethesda, MD 20814) V.1- 1921- Volume(issue)/page/year: 19,472,1939 TOXICOLOGY REVIEW FNSCA6 Forensic Science. (Lausanne, Switzerland) V.1-11, 1972-78. For pub lisher information, see FSINDR. Volume(issue)/page/year: 2,67,1973 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 84678 No. of Facilities: 101 (estimated) No. of Industries: 2 No. of Occupations: 7 No. of Employees: 3166 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 84678 No. of Facilities: 23 (estimated) No. of Industries: 1 No. of Occupations: 3 No. of Employees: 831 (estimated) No. of Female Employees: 510 (estimated)

毒理学数据：

急性毒性：口服-大鼠 LD50: 250 毫克/公斤; 口服-小鼠LD50: 345 毫克/公斤

异戊巴比妥分子结构与计算化学数据

计算化学数据

1.疏水参数计算参考值（XlogP）:无

2.氢键供体数量:2

3.氢键受体数量:3

4.可旋转化学键数量:4

5.互变异构体数量:5

6.拓扑分子极性表面积75.3

7.重原子数量:16

8.表面电荷:0

9.复杂度:303

10.同位素原子数量:0

11.确定原子立构中心数量:0

12.不确定原子立构中心数量:0

13.确定化学键立构中心数量:0

14.不确定化学键立构中心数量:0

15.共价键单元数量:1

异戊巴比妥上游产品

脲乙基异戊基丙二酸二乙酯 5-ethyl-5-(3-methylbutyl)-2-sulfanylidene-1,3-diazinane-4,6-dione

异戊巴比妥下游产品

5-乙基-5-(3-羟基-3-甲基丁基)巴比妥酸 5-乙基-1,3-二甲基-5-(3-甲基丁基)-2,4,6(1H,3H,5H)-嘧啶三酮 5-乙基-5-(3-甲基丁基)-1-(苯基甲基)-1,3-二嗪农-2,4,6-三酮

异戊巴比妥

异戊巴比妥基本信息

异戊巴比妥制备方法及用途