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吗氯贝胺

吗氯贝胺用途

Moclobemide(Ro111163)是可逆的单胺氧化酶(MAO)抑制剂,IC50为6.1 μM,可作用于重度抑郁症。

吗氯贝胺名称

[ CAS 号 ]:
71320-77-9

[ 中文名 ]:
4-氯-N-2-(4-吗啉基)乙基苯甲酰胺

[ 英文名 ]:
Moclobemide

[中文别名 ]:

[英文别名 ]:

4-chloro-N-[2-(morpholin-4-yl)ethyl]benzamide
Moclamide
moclbemide
Manefix
Moclobemide
aurorix
4-Chloro-N-(2-(4-morpholinyl)ethyl)benzamide
4-Chloro-N-[2-(4-morpholinyl)ethyl]benzamide
MFCD00865388
Moclobemidum

吗氯贝胺生物活性

[ 描述 ]:

Moclobemide(Ro111163)是可逆的单胺氧化酶(MAO)抑制剂,IC50为6.1 μM,可作用于重度抑郁症。

[ 相关类别 ]:

信号通路 >> 神经信号通路 >> 单胺氧化酶

研究领域 >> 神经疾病

[参考文献]

[1]. Da Prada, M., et al., Neurochemical profile of moclobemide, a short-acting and reversible inhibitor of monoamine oxidase type A. J Pharmacol Exp Ther, 1989. 248(1): p. 400-14.

[2]. Verleye, M., et al., Moclobemide attenuates anoxia and glutamate-induced neuronal damage in vitro independently of interaction with glutamate receptor subtypes. Brain Res, 2007. 1138: p. 30-8.

[3]. Reul, J.M., et al., Hypothalamic-pituitary-adrenocortical axis changes in the rat after long-term treatment with the reversible monoamine oxidase-A inhibitor moclobemide. Neuroendocrinology, 1994. 60(5): p. 509-19.

[相关活性小分子]

吗氯贝胺物理化学性质

[ 密度 ]:
1.2±0.1 g/cm3

[ 沸点 ]:
447.7±40.0 °C at 760 mmHg

[ 熔点 ]:
137°C

[ 分子式 ]:
C₁₃H₁₇ClN₂O₂

[ 分子量 ]:
268.739

[ 闪点 ]:
224.6±27.3 °C

[ 精确质量 ]:
268.097870

[ PSA ]:
41.57000

[ LogP ]:
0.84

[ 外观性状 ]:
白色至灰白色固体

[ 蒸汽压 ]:
0.0±1.1 mmHg at 25°C

[ 折射率 ]:
1.550

[ 储存条件 ]:
Room temp

吗氯贝胺MSDS

吗氯贝胺毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: CV2462000

CHEMICAL NAME :: Benzamide, 4-chloro-N-(2-(4-morpholinyl)ethyl)-

CAS REGISTRY NUMBER :: 71320-77-9

LAST UPDATED :: 199803

DATA ITEMS CITED :: 6

MOLECULAR FORMULA :: C13-H17-Cl-N2-O2

MOLECULAR WEIGHT :: 268.77

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 5 mg/kg/5W-I

TOXIC EFFECTS :: Skin and Appendages - hair

REFERENCE :: HUPSEC Human Psychopharmacology. (John Wiley & Sons Ltd., Baffins Lane, Chichester, W.Sussex PO19 1UD, United Kingdom) V.1- 1986- Volume(issue)/page/year: 12,81,1997

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 19 mg/kg

TOXIC EFFECTS :: Behavioral - sleep Behavioral - hallucinations, distorted perceptions Gastrointestinal - nausea or vomiting

REFERENCE :: JCLPDE Journal of Clinical Psychiatry. (Physicians Postgraduate Press, Inc., POB 240008, Memphis, TN 38124) V.39- 1978- Volume(issue)/page/year: 47,438,1986

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 66 mg/kg/11D-I

TOXIC EFFECTS :: Vascular - BP elevation not characterized in autonomic section

REFERENCE :: LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 346,1032,1995

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 12600 mg/kg/14D-I

TOXIC EFFECTS :: Blood - thrombocytopenia Blood - leukemia Skin and Appendages - dermatitis, other (after systemic exposure)

REFERENCE :: LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 347,1329,1996

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 707 mg/kg

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

REFERENCE :: USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #4210754

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 591 mg/kg

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

REFERENCE :: EJMCA5 European Journal of Medicinal Chemistry--Chimie Therapeutique. (Editions Scientifiques Elsevier, 29 rue Buffon, F-75005, Paris, France) V.9- 1974- Volume(issue)/page/year: 31,909,1996

吗氯贝胺安全信息

[ 符号 ]:

GHS05, GHS07

[ 信号词 ]:
Danger

[ 危害声明 ]:
H302-H315-H318-H335

[ 警示性声明 ]:
P261-P280-P305 + P351 + P338

[ 个人防护装备 ]:
dust mask type N95 (US);Eyeshields;Gloves

[ 危害码 (欧洲) ]:
Xn: Harmful;

[ 风险声明 (欧洲) ]:
R22

[ 安全声明 (欧洲) ]:
S26-S39

[ 危险品运输编码 ]:
3249

[ RTECS号 ]:
CV2462000

[ 包装等级 ]:
III

[ 危险类别 ]:
6.1(b)

吗氯贝胺合成路线

吗氯贝胺上下游产品

吗氯贝胺上游产品

吗氯贝胺下游产品

吗氯贝胺制备

方法1：溴乙胺氢溴酸盐溶于水中和苯中，滴加5%氢氧化钠，分去水层，加入吡啶，在25℃滴加对氯苯甲酰氯。回流后放冷，抽滤，水洗，干燥，用苯重结晶，得酰胺产物，收率91.8%。该酰胺和吗啉及乙酸乙酯一起搅拌，加入水，用盐酸调至Ph值1～2。分去酯层，用乙酸乙酯提取2次，水层用10%氢氧化钠中和至Ph值8～9。滤集固体，用异丙醇重结晶，得白色针状结晶的吗氯贝胺，收率80.2%，熔点136～137℃。总收率可达73.6%。
也可如下操作。溴乙胺氢溴酸盐溶于水中，在0～5℃和剧烈搅拌下，同时滴加对氯苯甲酰氯及氢氧化钠溶液。加毕继续反应，可得酰胺产物，收率98.7%。该酰胺和吗啉搅拌回流，即可简单地得到吗氯贝胺，粗品经异丙醇重结晶，收率75.3%，熔点136～137℃。总收率可达74.3%。
方法2：丙烯酰胺溶于水中，低温下和吗啉进行加成反应。生成的吗啉基丙酰胺溶液，不用经过处理，直接加入次氯酸钠的碱性溶液进行Hofmann降解，经后处理可得吗啉基乙胺，收率42.3%，沸点99～100℃/3．2kPa，n_D²⁰1.4739。
对氯苯甲酸和氯甲酸乙酯在丙酮溶液中，三乙胺存在下，反应生成对氯苯甲酰氧基甲酸乙酯，该混合酸酐有很强的反应活性，和上述得到的吗啉乙胺反应即得吗氯贝胺，收率58.9%，熔点136～137℃。该法反应步骤虽较长，但所用原料较简单。

2. N-(2-羟乙基)对氯苯甲酰胺的制备

在反应瓶中加入对氯苯甲酸125g(0.8mol)、甲醇300ml和浓H2SO48.5g(0.16mol),搅拌回流4h.减压蒸除甲醇,加入冰水,搅拌,过滤,冷水洗滤饼,抽干,得白色固体.将该固体加到反应瓶,加入乙醇胺76ml(1.3mol)和适量氯化铵,搅拌回流3h.冷却,倒入冰水中,过滤,滤饼用5%氢氧化钠水溶液洗,无水乙醇洗,抽干,干燥得白色晶体N-(2-羟乙基)对氯苯甲酰胺129.6g,收率78.1%,mp110~115ºC.

3. N-(2-氯乙基)对氯苯甲酰胺的制备

在反应瓶中加入N-(2-羟乙基)对氯苯甲酰胺85g(0.43mol)、二氯甲烷250ml,室温及搅拌下慢慢滴加氯化亚砜93ml(1.28mol),滴加过程控制内温不超过25ºC,滴毕,于40~50ºC搅拌反应1h.反应毕,减压蒸除溶剂和过量的SOCl2.向剩余物中加入冰水,搅拌,过滤,滤饼水洗至中性,干燥,甲苯重结晶,得类白色晶体N-(2-氯乙基)对氯苯甲酰胺83.2g,收率89.8%,mp104~106ºC.

4. 吗氯贝胺的合成

在反应瓶中加入N-(2-氯乙基)对氯苯甲酰胺54.5g(0.5mol)、吗啉43.5g(0.5mol)、无水Na2CO3 26.5g(0.25mol) 和甲苯250ml.搅拌回流5h.冷却,过滤,滤饼水洗至中性,用50%异丙醇水溶液重结晶,过滤,干燥,得白色晶体吗氯贝胺40.7g,收率60.7%,mp136~139ºC.含量≥99.0%(HPLC归一法).

吗氯贝胺文献

Antidepressant-like effect of the novel MAO inhibitor 2-(3,4-dimethoxy-phenyl)-4,5-dihydro-1H-imidazole (2-DMPI) in mice.

Prog. Neuropsychopharmacol. Biol. Psychiatry 39(1) , 31-9, (2012)

Monoamine oxidase (MAO) inhibitors were the first antidepressant drugs to be prescribed and are still used today with great success, especially in patients resistant to other antidepressants. In this ...

[Serotonin syndrome in the course of drug-poisoning--case presentation].

Prz. Lek. 68(8) , 523-6, (2011)

Serotonin syndrome is caused by excess serotonin in the central nervous system. It usually occurs as adverse drug-therapy (neuroleptic agents, monoamine oxidase inhibitors, serotonin reuptake inhibito...

[Obstructive sleep apnoea syndrome as the cause of atypical depression].

Fortschr. Neurol. Psychiatr. 79(9) , 531-4, (2011)

Sleep apnoea is a common disorder presenting with somatic comorbidities and psychiatric symptoms. This case report describes a 43-year-old man with an organic depressive disorder due to obstructive sl...

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