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阿尼西坦

阿尼西坦用途

Aniracetam(Ro 13-5057)可调节AMPA受体和nAChR,具有神经保护和益智作用。

阿尼西坦名称

[ CAS 号 ]:
72432-10-1

[ 中文名 ]:
阿尼西坦

[ 英文名 ]:
Aniracetam

[中文别名 ]:

[英文别名 ]:

MFCD00153767
Ro 13-5057
Aniracetam
1-p-Anisoyl-2-pyrrolidinone
Sarpul
1-(4-Methoxybenzoyl)pyrrolidin-2-one
Ampamet
Draganon
1-[(4-Methoxyphenyl)carbonyl]pyrrolidin-2-on
2-Pyrrolidinone, 1-(4-methoxybenzoyl)-

阿尼西坦生物活性

[ 描述 ]:

Aniracetam(Ro 13-5057)可调节AMPA受体和nAChR,具有神经保护和益智作用。

[ 相关类别 ]:

信号通路 >> 跨膜转运 >> iGluR

信号通路 >> 神经信号通路 >> iGluR

信号通路 >> 跨膜转运 >> 胆碱受体

信号通路 >> 神经信号通路 >> 胆碱受体

研究领域 >> 神经疾病

[参考文献]

[1]. Nakamura K, et al. Anxiolytic effects of aniracetam in three different mouse models of anxiety and the underlying mechanism. Eur J Pharmacol. 2001 May 18;420(1):33-43.

[2]. Vaglenova J, et al. Aniracetam reversed learning and memory deficits following prenatal ethanol exposure by modulating functions of synaptic AMPA receptors. Neuropsychopharmacology. 2008 Apr;33(5):1071-83. Epub 2007 Jul 4.

[相关活性小分子]

阿尼西坦物理化学性质

[ 密度 ]:
1.2±0.1 g/cm3

[ 沸点 ]:
399.7±34.0 °C at 760 mmHg

[ 熔点 ]:
−58 °C(lit.)

[ 分子式 ]:
C₁₂H₁₃NO₃

[ 分子量 ]:
219.236

[ 闪点 ]:
195.5±25.7 °C

[ 精确质量 ]:
219.089539

[ PSA ]:
46.61000

[ LogP ]:
0.27

[ 外观性状 ]:
白色结晶或结晶粉末

[ 蒸汽密度 ]:
4.9 (vs air)

[ 蒸汽压 ]:
0.0±0.9 mmHg at 25°C

[ 折射率 ]:
1.574

[ 储存条件 ]:
Store at RT

[ 水溶解性 ]:
Reacts

阿尼西坦MSDS

详细MSDS(安全技术说明书)

阿尼西坦毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UY5781900

CHEMICAL NAME :: 2-Pyrrolidinone, 1-(4-methoxybenzoyl)-

CAS REGISTRY NUMBER :: 72432-10-1

LAST UPDATED :: 199806

DATA ITEMS CITED :: 10

MOLECULAR FORMULA :: C12-H13-N-O3

MOLECULAR WEIGHT :: 219.26

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 :: 4500 mg/kg

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

REFERENCE :: PSCHDL Psychopharmacology (Berlin). (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094) V.47- 1976- Volume(issue)/page/year: 78,104,1982

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1255 mg/kg

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

REFERENCE :: MDACAP Medicamentos de Actualidad. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1965- Volume(issue)/page/year: 30,9,1994

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/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: -,45,1995

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >50 mg/kg

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

REFERENCE :: MDACAP Medicamentos de Actualidad. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1965- Volume(issue)/page/year: 30,9,1994

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3648 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Gastrointestinal - changes in structure or function of salivary glands

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 14(Suppl 4),673,1986

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1180 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - lacrimation Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 14(Suppl 4),673,1986

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >5 gm/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: -,45,1995

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >100 mg/kg

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

REFERENCE :: MDACAP Medicamentos de Actualidad. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1965- Volume(issue)/page/year: 30,9,1994

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: >2 gm/kg

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

REFERENCE :: MDACAP Medicamentos de Actualidad. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1965- Volume(issue)/page/year: 30,9,1994 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 26400 mg/kg

SEX/DURATION :: female 7-17 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 14(Suppl 4),691,1986

阿尼西坦安全信息

[ 个人防护装备 ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ 危险品运输编码 ]:
NONH for all modes of transport

[ WGK德国 ]:
2

[ RTECS号 ]:
UY5781900

阿尼西坦合成路线

详细合成路线

阿尼西坦上下游产品

阿尼西坦上游产品

阿尼西坦下游产品

阿尼西坦制备

方法1：2-吡咯烷酮和对甲氧基苯甲酰氯在乙醚中，三乙胺存在下，于0～10℃回流3h，得茴拉西坦。

方法2：对甲氧基苯甲酸和氯化亚砜反应，得对甲氧基苯甲酰氯(收率90%)。然后对甲氧基苯甲酰氯先和4-氨基丁酸在氢氧化钠的水溶液中、三乙基苄铵盐(TEBA)存在下反应，得4-(4-甲氧基苯甲酰基)氨基丁酸(收率69.4%) 后，再在甲苯中，二氯亚砜存在下环合，得茴拉西坦，收率80.4%，熔点118～120℃。

方法3：对甲氧基苯甲酸氯化为对甲氧基苯甲酰氯后，再和2-吡咯烷酮钠在四氢呋喃中、4-二甲氨基吡啶(DMAP)存在下反应，即得茴拉西坦，收率76.2%(以对甲氧基苯甲酰氯计)，熔点118～119℃。

方法4：2-吡咯烷酮在含甲醇钠的甲苯中，回流1h后，再蒸尽甲醇。在10℃加入TEBA，滴加对甲氧基苯甲酰氯的甲苯溶液，在室温下搅拌0.5h，再在50℃下搅拌6h。处理后得茴拉西坦，收率85%(以2-吡咯烷酮计)，熔点120～121℃。

方法5：2-吡咯烷酮和三乙胺混合，在0～10℃：滴加三甲基氯硅烷。加毕，室温反应2h。加入对甲氧基苯甲酰氯的二氧六环溶液，在40℃下搅拌2h，得茴拉西坦，收率65%。

阿尼西坦文献

Piracetam defines a new binding site for allosteric modulators of alpha-amino-3-hydroxy-5-methyl-4-isoxazole-propionic acid (AMPA) receptors.

J. Med. Chem. 53 , 2197-203, (2010)

Glutamate receptors are the most prevalent excitatory neurotransmitter receptors in the vertebrate central nervous system and are important potential drug targets for cognitive enhancement and the tre...

Glutamate Receptors within the Mesolimbic Dopamine System Mediate Alcohol Relapse Behavior.

J. Neurosci. 35 , 15523-38, (2015)

Glutamatergic input within the mesolimbic dopamine (DA) pathway plays a critical role in the development of addictive behavior. Although this is well established for some drugs of abuse, it is not kno...

Development and validation of a liquid chromatographic method for the simultaneous determination of aniracetam and its related substances in the bulk drug and a tablet formulation.

J. Pharm. Biomed. Anal. 56(3) , 615-22, (2011)

Simultaneous determination of aniracetam and its related impurities (2-pyrrolidinone, p-anisic acid, 4-p-anisamidobutyric acid and (p-anisoyl)-4-methyl-2-pyrrolidinone) was accomplished in the bulk dr...

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