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Chemistry

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Also known as: 123-39-7, Methylformamide, Formamide, n-methyl-, Monomethylformamide, N-formylmethylamine, N-methyl-formamide
Molecular Formula
C2H5NO
Molecular Weight
59.07  g/mol
InChI Key
ATHHXGZTWNVVOU-UHFFFAOYSA-N
FDA UNII
XPE4G7Y986

Methylformamide
N-Methylformamide is a water-soluble organic solvent. As an adjuvant antineoplastic agent, N-methylformamide depletes cellular glutathione, a key molecule involved in the antioxidation of reactive oxygen species (ROS) and other free radicals, thereby enhancing ionizing radiation-induced DNA cross-linking in and terminal differentiation of tumor cells. (NCI04)
1 2D Structure

Methylformamide

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
N-methylformamide
2.1.2 InChI
InChI=1S/C2H5NO/c1-3-2-4/h2H,1H3,(H,3,4)
2.1.3 InChI Key
ATHHXGZTWNVVOU-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CNC=O
2.2 Other Identifiers
2.2.1 UNII
XPE4G7Y986
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Methylformamide

2. Monomethylformamide

3. Nsc 3051

2.3.2 Depositor-Supplied Synonyms

1. 123-39-7

2. Methylformamide

3. Formamide, N-methyl-

4. Monomethylformamide

5. N-formylmethylamine

6. N-methyl-formamide

7. Nsc 3051

8. N-monomethylformamide

9. Ek 7011

10. Hconhch3

11. X 188

12. Formamide, Methyl-

13. Methylimidoformic Acid

14. N-methyl-formimidic Acid

15. Nmf

16. (e)-methylimidoformic Acid

17. (z)-methylimidoformic Acid

18. Chebi:7438

19. Xpe4g7y986

20. Nsc3051

21. N-methyl-formic Acid-amide

22. Nsc-3051

23. N-methylformamide, 99%

24. Methanimidic Acid, Methyl-

25. N-methyl Formamide

26. Formic Acid Amide, N-methyl-

27. Hsdb 100

28. Einecs 204-624-6

29. Brn 1098352

30. Unii-xpe4g7y986

31. Ai3-26076

32. N-methylcarboxamide

33. N-methylmethanamide

34. Methyl-methanimidic Acid

35. N-methylformamide-[18o]

36. N-methyl Formic Acid Amide

37. Wln: Vhm1

38. Ec 204-624-6

39. Chembl9240

40. Formamide, N-methyl- ( )

41. 4-04-00-00170 (beilstein Handbook Reference)

42. N-methylformamide [mi]

43. Dtxsid0025608

44. N-methylformamide [hsdb]

45. Zinc8214610

46. Bbl027430

47. Mfcd00003280

48. Stl146549

49. Akos000118787

50. Sb85388

51. Nci60_002574

52. Db-046834

53. F0059

54. Ft-0638572

55. Ft-0652807

56. A805066

57. Q138742

58. J-004934

59. F0001-0365

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 59.07 g/mol
Molecular Formula C2H5NO
XLogP3-1
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count0
Exact Mass59.037113783 g/mol
Monoisotopic Mass59.037113783 g/mol
Topological Polar Surface Area29.1 Ų
Heavy Atom Count4
Formal Charge0
Complexity20
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

NMF is an investigational anticancer drug... .

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. 175


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Antineoplastic Agents

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)


Radiation-Sensitizing Agents

Drugs used to potentiate the effectiveness of radiation therapy in destroying unwanted cells. (See all compounds classified as Radiation-Sensitizing Agents.)


5.2 Absorption, Distribution and Excretion

8 healthy male subjects were exposed to dimethylformamide vapor at a concn of 8.79 + or - 0.33 ppm for 6 hr/day for 5 consecutive days. All urine voided by the subjects was collected from the beginning of the first exposure to 24 hr past the end of the last exposure & each sample was analyzed for monomethylformamide. Monomethylformamide was rapidly eliminated from the body with urine values peaking within a few hr following the end of each exposure period. The mean for the 7 hr (end of exposure) sample was 4.74 ug/ml urine or 736.8 ug.

PMID:627935 Krivanek ND et al; J Occup Med 20 (3): 179-182 (1978)


Dimethylformamide reached an average level of 2.8 mg/l in the blood of subjects exposed to 21 ppm of the vapor for 4 hr, & was undetectable at 4 hr after the exposure; the metabolite, methylformamide, averaged between 1 & 2 mg/l in the blood & this level was maintained for at least 4 hr after exposure. Maximal blood levels of about 14 & 8 mg/l were observed for dimethylformamide & methylformamide, respectively, at 0 & 3 hrs, after a 4 hr exposure to 87 ppm of the vapor. Repeated daily exposures to 21 ppm of dimethylformamide did not result in accumulation of the chemical or its metabolite in blood. /Dimethylformamide and methylformamide/

Baselt, R.C. Biological Monitoring Methods for Industrial Chemicals. 2nd ed. Littleton, MA: PSG Publishing Co., Inc. 1988., p. 128


5.3 Metabolism/Metabolites

It is known that dimethylformamide is metabolized in man by sequential N-demethylation to methylformamide & formamide, which are largely eliminated in the urine.

Baselt, R.C. Biological Monitoring Methods for Industrial Chemicals. 2nd ed. Littleton, MA: PSG Publishing Co., Inc. 1988., p. 128


In mice, NMF is metabolized mainly to carbon dioxide, which is exhaled with the breath, & to methylamine, which is excreted with the urine. Of the radioactivity injected with [C14]formyl-NMF (400 mg/kg), 39% was exhaled as carbon dioxide. The amount of the drug excreted unchanged in the urine in mice was only 26% & 15% of the dose was metabolized to methylamine. A mercapturate, N-acetyl-S-(N-methylcarbamoyl)cysteine was identified as a major metabolite of NMF in the urine of mice, rats, & patients. Formation of the novel metabolite involves oxidation of the formyl moiety & subsequent conjugation with glutathione. On GLC analysis of the urine of mice which had received NMF, small amounts of formamide were also detected. Some evidence suggests that this metabolite was actually N-hydroxy-methylformamide, the immediate product of N-methyl-C-hydroxylation of NMF, & not formamide. N-Hydroxymethylformamide, like N-hydroxymethyl-N-methylformamide, the principal metabolite of dimethylformamide, is thermally labile & breaks down to give formamide & formaldehyde; but it is stable in aqueous soln. In alkaline soln N-hydroxymethylformamide undergoes facile hydrolysis. Only 14% of the radioactivity injected with [C14]methyl-NMF was exhaled as labeled carbon dioxide. Formate was not a urinary metabolite of NMF in mice.

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. 170


N-methylformamide has known human metabolites that include Methyl Isocyanate.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.4 Mechanism of Action

The mechanism by which NMF causes hepatotoxicity is currently under investigation. Evidence is accumulating which suggests that a reactive metabolite of NMF is involved. In vitro NMF was cytotoxic only at concns in the 0.1 M range whereas the maximum NMF concn in the plasma of animals which showed evidence of hepatotoxicity was below 0.01 M. The hypothesis that a reactive metabolite is formed which might be responsible for NMF-induced hepatotoxicity is supported by the following findings: 1) NMF caused the depletion of hepatic glutathione levels in vivo, & in hepatocytes in vitro; 2) an NMF metabolite (or metabolites) was covalently bound to liver microsomal protein; & 3) pretreatment of mice with cysteine or N-acetylcysteine protected against NMF-induced hepatotoxicity. Liver mitochondria may be a target for the reactive metab, as NMF has been shown to inhibit the ability of mouse liver mitochondria to sequester calcium ions when a hepatotoxic dose was admin ip.

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. 174


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Methylformamide manufacturers, exporters & distributors 1

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PharmaCompass offers a list of Methylformamide API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right Methylformamide manufacturer or Methylformamide supplier for your needs.

Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Methylformamide manufacturer or Methylformamide supplier.

PharmaCompass also assists you with knowing the Methylformamide API Price utilized in the formulation of products. Methylformamide API Price is not always fixed or binding as the Methylformamide Price is obtained through a variety of data sources. The Methylformamide Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

API | Excipient name

Methylformamide

Synonyms

123-39-7, Formamide, n-methyl-, Monomethylformamide, N-formylmethylamine, N-methyl-formamide, Nsc 3051

Cas Number

123-39-7

Unique Ingredient Identifier (UNII)

XPE4G7Y986

About Methylformamide

N-Methylformamide is a water-soluble organic solvent. As an adjuvant antineoplastic agent, N-methylformamide depletes cellular glutathione, a key molecule involved in the antioxidation of reactive oxygen species (ROS) and other free radicals, thereby enhancing ionizing radiation-induced DNA cross-linking in and terminal differentiation of tumor cells. (NCI04)

Methylformamide Manufacturers

A Methylformamide manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Methylformamide, including repackagers and relabelers. The FDA regulates Methylformamide manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Methylformamide API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Methylformamide Suppliers

A Methylformamide supplier is an individual or a company that provides Methylformamide active pharmaceutical ingredient (API) or Methylformamide finished formulations upon request. The Methylformamide suppliers may include Methylformamide API manufacturers, exporters, distributors and traders.

click here to find a list of Methylformamide suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Methylformamide USDMF

A Methylformamide DMF (Drug Master File) is a document detailing the whole manufacturing process of Methylformamide active pharmaceutical ingredient (API) in detail. Different forms of Methylformamide DMFs exist exist since differing nations have different regulations, such as Methylformamide USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Methylformamide DMF submitted to regulatory agencies in the US is known as a USDMF. Methylformamide USDMF includes data on Methylformamide's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Methylformamide USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Methylformamide suppliers with USDMF on PharmaCompass.

Methylformamide GMP

Methylformamide Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Methylformamide GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Methylformamide GMP manufacturer or Methylformamide GMP API supplier for your needs.

Methylformamide CoA

A Methylformamide CoA (Certificate of Analysis) is a formal document that attests to Methylformamide's compliance with Methylformamide specifications and serves as a tool for batch-level quality control.

Methylformamide CoA mostly includes findings from lab analyses of a specific batch. For each Methylformamide CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Methylformamide may be tested according to a variety of international standards, such as European Pharmacopoeia (Methylformamide EP), Methylformamide JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Methylformamide USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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