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N-Methylpyrrolidone

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Also known as: 872-50-4, N-methylpyrrolidone, N-methyl-2-pyrrolidone, 1-methylpyrrolidin-2-one, 1-methyl-2-pyrrolidone, Methylpyrrolidone

Molecular Formula

C₅H₉NO

Molecular Weight

99.13 g/mol

InChI Key

SECXISVLQFMRJM-UHFFFAOYSA-N

FDA UNII

JR9CE63FPM

methylpyrrolidone is a natural product found in Microtropis japonica, Melicope hayesii, and Glycyrrhiza glabra with data available.

1 2D Structure

N-Methylpyrrolidone

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-methylpyrrolidin-2-one

2.1.2 InChI

InChI=1S/C5H9NO/c1-6-4-2-3-5(6)7/h2-4H2,1H3

2.1.3 InChI Key

SECXISVLQFMRJM-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CN1CCCC1=O

2.2 Other Identifiers

2.2.1 UNII

JR9CE63FPM

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1-methyl-2-pyrrolidinone, 1-methyl-(14)c-labeled

2. 1-methyl-2-pyrrolidinone, 2,3,4,5-(14)c-labeled

3. Methyl Pyrrolidone

4. N-methyl-2-pyrrolidinone

5. N-methyl-2-pyrrolidone

6. N-methylpyrrolidinone

7. N-methylpyrrolidone

8. Pharmasolve

2.3.2 Depositor-Supplied Synonyms

1. 872-50-4

2. N-methylpyrrolidone

3. N-methyl-2-pyrrolidone

4. 1-methylpyrrolidin-2-one

5. 1-methyl-2-pyrrolidone

6. Methylpyrrolidone

7. N-methyl-2-pyrrolidinone

8. M-pyrol

9. N-methylpyrrolidinone

10. 1-methylpyrrolidinone

11. 1-methylpyrrolidone

12. Methyl Pyrrolidone

13. 2-pyrrolidinone, 1-methyl-

14. N-methyl-pyrrolidone

15. 1-methyl-5-pyrrolidinone

16. 1-methylazacyclopentan-2-one

17. N-methylpyrrolidin-2-one

18. Nmp

19. N-methyl-gamma-butyrolactam

20. N-methyl Pyrrolidone

21. 1-methylpyrrolidine-2-one

22. N-methyl Pyrrolidinone

23. Methyl-2-pyrrolidinone

24. 1-methyl-2-pyrrolidon

25. Methylpyrrolidinone

26. Methylpyrrolidone [nf]

27. N-methylpyrrolid-2-one

28. N-methyl-alpha-pyrrolidone

29. Nsc 4594

30. Agsolex 1

31. 2687-44-7

32. N-methyl-alpha-pyrrolidinone

33. Nsc-4594

34. Mfcd00003193

35. Jr9ce63fpm

36. 51013-18-4

37. 1-methyl-pyrrolidin-2-one

38. N-methyl-.alpha.-pyrrolidone

39. Chembl12543

40. N-methyl-.gamma.-butyrolactam

41. Chebi:7307

42. N-methyl-.alpha.-pyrrolidinone

43. Dtxsid6020856

44. 1-methyl-2-pyrrolidinone, Anhydrous

45. 1-methyl-2-pyrrolidinone, Hplc Grade

46. 2-pyrrolidinone, 1-methyl-, Homopolymer

47. Dsstox_cid_856

48. N 0131

49. Dsstox_rid_75828

50. Dsstox_gsid_20856

51. 26876-92-6

52. N-methyl-pyrrolidinone

53. Pharmasolve

54. 2-pyrrolidinone, Methyl-

55. N-methylpyrrolidon

56. Cas-872-50-4

57. Ccris 1633

58. Methylpyrrolidone, N-

59. Hsdb 5022

60. Pyrrolidinone, Methyl-

61. N-methyl-2-pyrrolidon

62. 1-methyl-2-pyrolidone

63. Einecs 212-828-1

64. Unii-jr9ce63fpm

65. N-methyl-pyrrolidin-2-one

66. 1-methyl-2-pyrrolidinone, Puriss. P.a., >=99.0% (gc)

67. Micropure Ultra

68. Ai3-23116

69. N-methylpyrolidone

70. N-methypyrrolidone

71. Max-1 Peptide

72. Pyrol M

73. N-methylpirrolidone

74. 1methylpyrrolidinone

75. N-methyl Pyrrolidon

76. N-methylbutyrolactam

77. N-methy Pyrrolidone

78. N-methyl-pyrolidone

79. N-methyl-pyrrolidon

80. N-methylpyrolidinone

81. 1-methylpyrolidinone

82. Microposit 2001

83. N-methylpyrollidinone

84. N-methlypyrrolidinone

85. N-methyl Pirrolidone

86. N-methyl Pyrollidone

87. N-methyl-pyrollidone

88. N-methylpyrrolidone-

89. Nmp,sp Grade

90. 1-methyl Pyrrolidone

91. 1-methyl-pyrrolidone

92. Methyl-2-pyrrolidone

93. N-methy Pyrrolidinone

94. N-methyl Pyrolidinone

95. N-methyl-pyrolidinone

96. N-methyl- Pyrrolidone

97. N-methylpyrro-lidinone

98. N-methylpyrroli-dinone

99. N-methylpyrrolidin-one

100. 1-methyl-2pyrrolidone

101. 1-methyl2-pyrrolidone

102. 1methyl-2-pyrrolidone

103. 1-methyl Pyrrolidinone

104. 1-methyl-pyrrolidinone

105. Methylpyrrolidin-2-one

106. N-methy-2-pyrrolidone

107. N-methyl 2-pyrolidone

108. N-methyl-2-pyrolidone

109. 3p1d

110. N-methyl 2-pyrrolidone

111. N-methyl-2-pyrollidone

112. 1-methyl-2-pirrolidone

113. 1-methyl-2-pyroldinone

114. 1-methylpyrrolid-2-one

115. 1methyl-2-pyrrolidinone

116. N-methylpyrrolidine-2one

117. N-methyl-2-pyrolidinone

118. N-methyl-2-pyrrolidinon

119. N-methylpyrolidin-2-one

120. 1-methy-2-pyrrolidinone

121. 1-methyl-2-pyrolidinone

122. N-methyl 2-pyrrolidinone

123. N-methyl-2-pyrollidinone

124. N-methyl-pyrrolid-2-one

125. N-methylpyrollidin-2-one

126. 1 -methyl-2-pyrrolidone

127. 1-methyl 2-pyrrolidinone

128. 1-methyl-2-pyrollidinone

129. 1-methyl-pyrrolin-2-one

130. N-methylpyrrolidone-(2)

131. Nmp, N-methylpyrrolidone

132. 1-methyl-pyrrolidin-2one

133. N-methylpyrrolidine-2-one

134. Wln: T5nvtj A

135. N-methyl -2-pyrrolidinone

136. 1 -methyl-2-pyrrolidinone

137. 1-methyl -2-pyrrolidinone

138. 1-methyl-2- Pyrrolidinone

139. Ec 212-828-1

140. 2-pyrrolidone, 1-methyl-

141. 1-methyl-pyrrolidine-2-one

142. 1-n-methyl-2-pyrrolidinone

143. N-methyl-pyrrolidin -2-one

144. 30207-69-3

145. 1-methylazacyclopentane-2-one

146. Gtpl9520

147. Methyl Pyrrolidone [ii]

148. 1-methyl-2- Pyrrolidin-2-one

149. 1-methylpyrrolidone [mi]

150. Methyl Pyrrolidone [inci]

151. Nsc4594

152. Methylpyrrolidone [usp-rs]

153. Hy-y1275

154. N-methylpyrrolidone [mart.]

155. Zinc3860621

156. Tox21_202350

157. Tox21_300097

158. 1-methyl-2-pyrrolidinone, 99.5%

159. Bdbm50353587

160. N-methyl Pyrrolidon (peptide Grade)

161. N-methylpyrrolidone [usp-rs]

162. S6282

163. Stl183295

164. N-methyl-2-pyrrolidinone Acs Reagent

165. Akos000120930

166. 1-methyl-2-pyrrolidinone, Biosolv(r)

167. Db12521

168. Sl 1332

169. 1-methyl-2-pyrrolidone, Reagent, Acs

170. 1-methyl-2-pyrrolidinone [hsdb]

171. Ncgc00247902-01

172. Ncgc00247902-02

173. Ncgc00253935-01

174. Ncgc00259899-01

175. Bp-31156

176. N-methylpyrrolidone [ep Monograph]

177. 1-methyl-2-pyrrolidone (low Water Content)

178. Am20110252

179. Cs-0017258

180. Ft-0608052

181. Ft-0672137

182. Ft-0698122

183. Ft-0700571

184. M0418

185. M3055

186. 1-methyl-2-pyrrolidinone, Analytical Standard

187. 1-methyl-2-pyrrolidinone, Anhydrous, 99.5%

188. 1-methyl-2-pyrrolidinone, For Hplc, >=99%

189. 1-methyl-2-pyrrolidinone, For Synthesis, 99%

190. D78116

191. M 0418

192. Q33103

193. Residual Solvent Class 2 - N-methylpyrrolidone

194. 1-methyl-2-pyrrolidinone, Reagentplus(r), 99%

195. 1-methyl-2-pyrrolidinone, Spectrophotometric Grade

196. 1-methyl-2-pyrrolidon 100 Microg/ml In Methanol

197. 2-pyrrolidone,1-methyl Mfc5 H9 N1 O1

198. A842053

199. 1-methyl-2-pyrrolidinone, Acs Reagent, >=99.0%

200. 1-methyl-2-pyrrolidon 1000 Microg/ml In Methanol

201. 2,5-dichloro-4,6-dimethyl Pyridine-3-carbonitrile

202. J-504921

203. J-803017

204. 1-methyl-2-pyrrolidinone, Biotech. Grade, >=99.7%

205. 1-methyl-2-pyrrolidinone, Electronic/cleanroom Grade

206. 1-methyl-2-pyrrolidinone, P.a., Acs Reagent, 99%

207. 1-methyl-2-pyrrolidone, Anhydrous, Water 40ppm Max.

208. 1-methyl-2-pyrrolidinone, Saj First Grade, >=98.0%

209. 1-methyl-2-pyrrolidinone, Spectrophotometric Grade, >=99%

210. 1-methyl-2-pyrrolidinone, Vetec(tm) Reagent Grade, 98%

211. 1-methyl-2-pyrrolidinone, For Metal Speciation Analysis, >=99.0% (gc)

212. Methylpyrrolidone, United States Pharmacopeia (usp) Reference Standard

213. 1-methyl-2-pyrrolidinone Solution, Aromatic Hydrocarbon Solvents Mixture (80/20 Ratio)

214. N-methylpyrrolidone, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₅H₉NO
Molecular Weight	99.13 g/mol
XLogP3	-0.5
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	0
Exact Mass	99.068413911 g/mol
Monoisotopic Mass	99.068413911 g/mol
Topological Polar Surface Area	20.3 Å²
Heavy Atom Count	7
Formal Charge	0
Complexity	90.1
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Teratogens

An agent that causes the production of physical defects in the developing embryo. (See all compounds classified as Teratogens.)

4.2 Absorption, Distribution and Excretion

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. ...

Snyder, R. (ed.). Ethel Browning's Toxicity and Metabolism of Industrial Solvents. 2nd ed. Volume II: Nitrogen and Phosphorus Solvents. Amsterdam-New York-Oxford: Elsevier, 1990., p. 240

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.

PMID:12433813 Payan JP et al; Drug Metab Dispos 30 (12): 1418-24 (2002)

Metabolism studies were performed using (14)C and tritium labeled N-methyl-2-pyrrolidinone in the rat. Male Sprague-Dawley rats were injected with labeled or unlabeled N-methyl-2-pyrrolidinone at 45 mg/kg body weight. Urine, feces, expired air, and bile were collected at various times between drug administration and sacrifice. For pharmacokinetic studies, serial blood samples were analyzed at times between 30 minutes and 6 hours post injection. HPLC of plasma N-methyl-2-pyrrlidinone indicated a rapid distribution phase followed by a slow elimination phase with a half life of approximately 7 hours for the (14)C and 10 hours for the tritium isotope. Urinary excretion accounted for approx 70% of the total dose within 12 hours, and a 2:1 ratio in the administered dose was maintained in the urine. The tissue distribution of the radiolabeled isomers showed similar patterns. The rank order of tissue accumulation from highest to lowest concentration was liver, intestine, testes, stomach, kidneys, lungs, brain, heart, pancreas, and spleen. The bladder, thyroid, and thymus showed minimal N-methyl-2-pyrrolidinone levels.

Wells DA, Digenis GA; Drug Metab & Disp 16 (2): 243-49 (1988)

Six male volunteers were exposed for eight hours on four different days to 0, 10, 25, and 50 mg/cu m N-methyl-2-pyrrolidone. ... N-Methyl-2-pyrrolidone was absorbed through the respiratory tract and readily eliminated from the body, mainly by biotransformation to other compounds. ...

PMID:9166128 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1128696 Akesson B, Paulsson K; Occupational and Environmental Medicine 54 (4): 236-40 (1997)

For more Absorption, Distribution and Excretion (Complete) data for 1-METHYL-2-PYRROLIDINONE (8 total), please visit the HSDB record page.

4.3 Metabolism/Metabolites

The aim was to study the metabolic pathway for N-methyl-2-pyrrolidone in humans. Three healthy male volunteers were administered 100 mg N-methyl-2-pyrrolidone orally. All urine was collected during nine consecutive days. The identification and quantification of the metabolites were performed by gas chromatography/mass spectrometry (GC/MS). N-Methyl-2-pyrrolidone, 5-hydroxy-N-methyl-2-pyrrolidone (5-hydroxy-N-methyl-2-pyrrolidone), N-methylsuccinimide, and 2-hydroxy-N-methylsuccinimide were found in urine. The mean excreted fractions for N-methyl-2-pyrrolidone, 5-hydroxy-N-methyl-2-pyrrolidone, N-methylsuccinimide, and 2-hydroxy-N-methylsuccinimide were 0.8%, 44%, 0.4%, and 20%, respectively. There was no conjugation with glucoronic acid or sulfate or either 5-hydroxy-N-methyl-2-pyrrolidone or 2-hydroxy-N-methylsuccinimide. One-third of the orally dosed N-methyl-2-pyrrolidone was not recovered in urine as either N-methyl-2-pyrrolidone, 5-hydroxy-N-methyl-2-pyrrolidone, N-methylsuccinimide, or 2-hydroxy-N-methylsuccinimide. The half-lives for 5-hydroxy-N-methyl-2-pyrrolidone, N-methylsuccinimide, and 2-hydroxy-N-methylsuccinimide in urine were approximately 4, 8, and 17 hr, respectively.

PMID:9029058 Akesson B, Jonsson BA; Drug Metab Dispos 25 (2): 267-9 (1997)

A method for determination of N-methylsuccinimide and 2-hydroxy-N-methylsuccinimide in human urine and of N-methylsuccinimide in human plasma was developed. N-Methylsuccinimide and 2-hydroxy-N-methylsuccinimide are metabolites of the ... organic solvent N-methyl-2-pyrrolidone. ... The method is applicable for analysis of urine and plasma samples from workers exposed to N-methyl-2-pyrrolidone.

Jonsson B AG, Akesson B; Journal of Chromatography B 704 (1-2): 151-8 (1997)

This study described the isolation and identification of the major urinary metabolite of N-methylpyrrolidinone in the male Sprague-Dawley-rat following intravenous administration. The rats were injected via the tail vein with either unlabeled N-methylpyrrolidinone or (14)C labeled N-methylpyrrolidinone at 45 mg/kg. Urine was collected during 0 to 12, 12 to 24, and 24 to 48 hours after dosing and analyzed by gas chromatography/mass spectrometry. Thermospray liquid chromatography/mass spectrometry was performed on samples purified using high performance liquid chromatography method. The major metabolite correlated with 5-hydroxy-N-methylpyrrolidinone based on thin layer chromatography and mass spectral comparisons with an authentic sample.

PMID:1346987 Wells DA et al; Drug Metabolism and Disposition 20 (1): 124-6 (1992)

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