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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
    CAS 872-50-4
    methylpyrrolidone is a natural product found in Microtropis japonica, Melicope hayesii, and Glycyrrhiza glabra with data available.
    1 2D Structure

    CAS 872-50-4

    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 Weight 99.13 g/mol
    Molecular Formula C5H9NO
    XLogP3-0.5
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count1
    Rotatable Bond Count0
    Exact Mass99.068413911 g/mol
    Monoisotopic Mass99.068413911 g/mol
    Topological Polar Surface Area20.3 Ų
    Heavy Atom Count7
    Formal Charge0
    Complexity90.1
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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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    Various Intermediates needed in India [ENA12151]
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    Various Intermediates needed in India [ENA12031]
    A third-party manufacturing company based in India that deals in the manufacturing of formulations is looking for suppliers of Various Intermediates for commercial purpose. The suppliers must support this enquiry with CoA. 1. CAS 461-58-5 (20 MT) Intermediate 2. CAS 506-59-2 (24 MT) Intermediate 3. CAS 123-86-4 (30 MT) Intermediate 4. CAS 100986-89-8 (3 MT - 5 MT) Intermediate 5. CAS 872-50-4 (1 MT) Intermediate 6. CAS 67-68-5 (1 MT) Intermediate
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    1-Methyl-2-pyrrolidone (CAS 872-50-4) Intermediate needed in India [ENA11056]
    A specialty pharmaceutical company engaged in the drug development, manufacturing and commercialization of pharmaceutical products is looking for suppliers of 1-Methyl-2-pyrrolidone (CAS 872-50-4) Intermediate for commercial purpose. The required quantity is 100 kg.
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    Various Intermediates needed in India [ENA10694]
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    22 Jun 2021

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