N-甲基吡咯烷酮 N-methylpyrrolidin-2-one

概况
编码系统
物化性质
计算性质
分类
ADME
晶体信息
安全信息
SDS

概况

中文名称

N-甲基吡咯烷酮； N-甲基吡咯烷； 1-甲基-2-吡咯烷酮； 1-甲基-吡咯烷酮； N-甲基吡咯烷酮（NMP）； N-甲基-A-吡咯烷酮；甲基吡咯烷酮
英文名称

N-methylpyrrolidin-2-one； 1-methyl-pyrrolidin-2-one； N-Methyl-2-pyrrolidone； N-methyl-2-pyrrolidon
化学式

C5H9NO
分子量

99.13
分类属性

氨，酰胺，氮，氧，五碳，四氢吡咯
类药性

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编码系统

CAS

872-50-4
MOL

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SMILES

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物化性质

物理描述 Physical Description

N-methyl-2-pyrrolidone appears as a clear colorless liquid with a "fishlike" odor. Denser than water. Flash point 199°F. Contact may irritate skin, eyes and mucous membranes. May be toxic by ingestion.
颜色/状态 Color Form

Clear liquid
气味 Odor

Mild amine odor
沸点 Boiling Point

202.0 °C
熔点 Melting Point

-24.0 °C
闪点 Flash Point

86 °C c.c.
溶解度 Solubility

greater than or equal to 100 mg/mL at 68° F (NTP, 1992)
密度 Density

1.027 at 25 °C/25 °C
蒸气密度 Vapor Density

3.4 (NTP, 1992) (Relative to Air)
蒸汽压力 Vapor Pressure

3.45X10-1 mm Hg at 25 °C
亨利常数 Henrys Law Constant

3.20e-09 atm-m3/mole
稳定性/保质期 Stability Shelf Life

NMP shows unlimited shelf life in tightly closed containers, slight discoloration does not impair its quality.
自燃温度 Autoignition Temperature

655 °F (346 °C)
分解 Decomposition

Decomposes on heating and on burning. This produces toxic fumes including nitrogen oxides and carbon monoxide.
粘度 Viscosity

1.65 cP at 25 °C
燃烧热 Heat Of Combustion

719 kcal/mol
汽化热 Heat Of Vaporization

127.3 kcal/Kg
表面张力 Surface Tension

40.7 dynes/cm
折光率 Refractive Index

MAX ABSORPTION (METHANOL): 205 NM (LOG E= 3.46); INDEX OF REFRACTION: 1.4684 AT 20 °C/D; SADTLER REFERENCE NUMBER: 6528 (IR, PRISM); 116 (VARIAN, NMR)
保留指数 Kovats Retention Index

1012;1004.6;1002;1034;1009
其他实验性质 Other Experimental Properties

Dipole moment at 25 °C: 4.09 debye; Dielectric constant at 25 °C: 32.3
辛醇/水分配系数 LogP

-0.38 (LogP)
氢离子浓度指数 pH

pH = 7.7-8

计算性质

辛醇/水分配系数 LogP

-0.5
重原子数 Heavy atoms count

7
可旋转键数 Rotatable bond count

0
环数 Number of rings

1
sp3杂化的碳原子比例 Carbon bond saturation (Fsp3)

0.8
拓扑面积 Polar surface area (Å)

20.3
氢给体数 Hydrogen bond donors count

0
氢受体数 Hydrogen bond acceptors count

1

ADME

吸收、分配和排泄

代谢

吸收、分配和排泄

Male Sprague-Dawley rats were given a single ip injection (45 mg/kg) of radiolabeled 1-methyl-2-pyrrolidone. Plasma levels of radioactivity and cmpd were monitored for six hr and the results suggested a rapid distribution phase which was followed by a slow elimination phase. The major amount of label was excreted in the urine within 12 hr and accounted for approximately 75% of the labelled dose. ...

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Hazardous Substances Data Bank (HSDB)

代谢

This study evaluated the toxicokinetics of N-((14)C)methylpyrrolidone (((14)C)NMP) after intravenous administration (0.1, 1, 10, 100, and 500 mg/kg, in saline solution) or topical application (20 and 40 uL/sq cm; 10 sq cm, neat) in haired male Sprague-Dawley rats. Whatever the dose, unchanged NMP was intensively distributed into the body with a volume of distribution of 69% of body weight. After this phase, unchanged NMP declined almost linearly with time for 3 to 4 hr after administration and then followed a mono-exponential function (t1/2 = 0.8 hr) for the three lowest doses. The maximal plasma level of 5-hydroxy-N-methylpyrrolidone (5-HNMP), the main metabolite, was reached 4 to 6 hr later for the three lowest doses and 8 to 24 hr later for the highest doses. These findings indicate that the elimination of NMP is governed by a saturable metabolism process. The Michaelis-Menten parameters estimated from plasma levels of unchanged NMP were 2 mM and 3.8 mg/hr, respectively. Between 4 and 10% of the administered doses were excreted in the urine as unchanged NMP. Urinary clearance of NMP (0.03 to 0.07 mL/min) indicates intensive tubular reabsorption. 5-HNMP was the main urinary metabolite and accounted for 42 to 55% of the administered doses. Its maximal urinary excretion occurred between 4 and 6 hr after administration of the three lowest doses and between 8 and 24 hr for the two highest doses. Urinary clearance (0.9 to 1.3 mL/min) was compatible with renal elimination by simple glomerular filtration.

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