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노르말메틸포름아미드 구조식 이미지
카스 번호:
x188;X 188;ek7011;EK 7011;nsc3051;HCONHCH3;NSC 3051;Methylformamide;Formylmethylamine;n-methyl-formamid
포뮬러 무게:
MOL 파일:

노르말메틸포름아미드 속성

-4 °C (lit.)
끓는 점
198-199 °C (lit.)
1.011 g/mL at 25 °C (lit.)
n20/D 1.432(lit.)
>230 °F
저장 조건
Sealed in dry,Room Temperature
soluble in water, chloroform, alcohols, acetone, ethylacetate but not in diethyl ether and petroleum ether
산도 계수 (pKa)
물리적 상태
Clear colorless
CAS 데이터베이스
123-39-7(CAS DataBase Reference)
Formamide, N-methyl-(123-39-7)
N-Methylformamide (123-39-7)
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 T
위험 카페고리 넘버 61-21-R61-R21
안전지침서 53-45-S53-S45
WGK 독일 1
RTECS 번호 LQ3000000
포장분류 II
HS 번호 29241990
유해 물질 데이터 123-39-7(Hazardous Substances Data)
독성 LD50 in mice (mg/kg): 2300 i.p.; 2600 orally; 1580 i.v.; 2700 i.m. (Langdon)
기존화학 물질 KE-24109
유해화학물질 필터링 2019-1-937
함량 및 규제정보 물질구분: 유독물질; 혼합물(제품)함량정보: 2019-1-937:N-메틸포름아미드[N-Methylformamide; 123-39-7] 및 이를 0.3% 이상 함유한 혼합물
신호 어: Danger
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H312 피부와 접촉하면 유해함 급성 독성 물질 - 경피 구분 4 경고 P280,P302+P352, P312, P322, P363,P501
H360 태아 또는 생식능력에 손상을 일으킬 수 있음 생식독성 물질 구분 1A, 1B 위험
P201 사용 전 취급 설명서를 확보하시오.
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P308+P313 노출 또는 접촉이 우려되면 의학적인 조치· 조언를 구하시오.
P405 밀봉하여 저장하시오.

노르말메틸포름아미드 C화학적 특성, 용도, 생산

화학적 성질



N-Methylformamide is used in amidation or transamidation chemical reactions where formamide is insufficient.




ChEBI: A member of the class of formamides having a N-methyl substituent.

생산 방법

N-Methylformamide (NMF) can be synthesized by: (1) reacting methylamine, carbon monoxide, methanol and a small amount of potassium acetate at 250 atm and 160°C; (2) heating methylamine with carbon monoxide and some sodium ethoxide in ethanol at 150 atm; (3) treating methylformate with methylamine and methanol; (4) reacting hexamethylenetetramine with formamide and hydrogen in the presence of Raney nickel at 130-145°C (Beilstein's Handbuch, 1977).

일반 설명

Clear colorless liquid with a slight amine odor.

공기와 물의 반응

Water soluble.

반응 프로필

N-Methylformamide is incompatible with benzene sulfonyl chloride. N-Methylformamide is also incompatible with strong oxidizing agents, acids, bases and acid chlorides. N-Methylformamide may react with chlorine, bromine, nitrates, nitric acid, triethylaluminum, potassium permanganate, chromic acid, chromic anhydride, chromium trioxide, borohydrides, hydrides, thionyl chloride, metallic sodium, phosphorus trioxide, diborane, (octafluoroisobutyrate + sodium nitrite) and (perchloryl fluoride + potassium methyl 4,4-dinitrobutyrate).


As NMF is an investigational anticancer drug, a number of clinical trials have been conducted with this chemical. The first clinical evaluation was initiated in 1956 (Laird Myers et al 1956). Five patients were treated with NMF; all but one patient received the drug orally. The dose ranged from 0.1 g to 4 g per day for 2-36 days. All patients showed symptoms of toxicity - chiefly anorexia, nausea, and vomiting. Hepatic damage as measured by liver function tests was seen in all patients at total doses between 80-870 mg/kg. The liver damage appeared to be reversible with cessation of treatment. Autopsy examination of the liver of one patient showed irregular lobular disorganization, some large hepatocytes and areas of liver regeneration. McVie et al (1984) administered NMF i.v. and orally to 19 patients at a starting dose of 300 mg/m2/day for 5 days. Treatment cycles were repeated every 2 weeks and doses were escalated to 1200 mg/m2/day for 5 days. Ettinger et al (1985) treated 35 patients with NMF i.v. at doses ranging from 125-3125 mg/m2 weekly every 6 weeks. The principal toxic effects of NMF were general malaise, nausea, vomiting and anorexia. Biochemical disturbances included reversible elevation of serum levels of transaminases in several patients. The occurrence of raised serum enzyme levels did not seem to be related to the dose. Other toxic symptoms were peripheral neuropathy and alcohol intolerance in a few patients
Eisenhauer et al (1986) conducted a phase 2 clinical trial which was terminated early because of NMF-induced hepatic and gastrointestinal toxicity.


N-Methylformamide is combustible.

공업 용도

NMF possesses excellent solvent properties that are similar to those of dimethylformamide. However, NMF appears to be much less important as an industrial solvent than dimethylformamide.

Safety Profile

Moderately toxic by ingestion, intraperitoneal, intravenous, intramuscular, and subcutaneous routes. An experimental teratogen. Experimental reproductive effects. An eye irritant. A very dangerous fire hazard when exposed to heat or flame. Violent reaction with benzene sulfonyl chloride. When heated to decomposition it emits toxic fumes of NOx.

신진 대사

In mice, NMF is metabolized mainly to carbon dioxide, which is exhaled with the breath, and to methylamine, which is excreted with the urine (Kestell et al 1985). Of the radioactivity injected with [14C]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% (Brindley et al 1982) and 15% of the dose was metabolized to methylamine (Kestell et al 1985). A mercapturate, N-acetyl-S-(Nmethylcarbamoyl)cysteine was identified as a major metabolite of NMF in the urine of mice, rats and patients (Kestell et al 1986). Formation of this novel metabolite involves oxidation of the formyl moiety and subsequent conjugation with glutathione (Threadgill et al 1987). On GLC analysis of the urine of mice which had received NMF, small amounts of formamide were also detected (Brindley et al 1982). Some evidence suggests that this metabolite was actually N-Hydroxy-methylformamide, the immediate product of N-methyl C-hydroxyla-tion of NMF, and not formamide (Kestell et al 1985). A^Hydroxymethylformamide, like N-hydroxymethyl-N-methylformamide, the principal metabolite of dimethylformamide, is thermally labile and breaks down to give formamide and formaldehyde; but it is stable in aqueous solution. In alkaline solution N-hydroxymethylformamide undergoes facile hydrolysis (Cooksey et al 1983). Only 14% of the radioactivity injected with [14C]methyl-NMF was exhaled as labeled carbon dioxide (Kestell et al 1985). Formate was not a urinary metabolite of NMF in mice (Kestell et al 1985).
When [14C]methyl-NMF (400 mg/kg) was injected i.p. in mice and drug plasma concentrations were determined during the first 24 h, the plasma concentration of radioactivity versus time curve was superimposable on the curve obtained by measuring unmetabolized NMF by GLC (Brindley et al 1982). Therefore, the metabolites of NMF appear to be rapidly eliminated from the blood into the urine. Radioactivity in the plasma was measurable for 8 days post NMF administration, but NMF was not detectable by GLC beyond 24 h after injection (Brindley et al 1982). The areas under the plasma concentration versus time curves after i.p., i.v. and oral administration of NMF in mice were found to be very similar (Brindley et al 1982). Similarly, the bioavailability of NMF was high in patients in a phase I clinical trial (Brindley et al 1983).
Contrary to an earlier report which claimed that NMF was biotransformed to formaldehyde by a rat liver homogenate (Barnes and Ranta, 1972), recent findings have shown that NMF does not undergo appreciable metabolism in vitro. Neither formaldehyde (or a formaldehyde precursor) could be detected as a metabolite of NMF in liver preparations or hepatocytes, nor was metabolism measurable as observed by the disappearance of substrate (Gescher et al 1982). However, NMF labeled with [14C] either in the methyl or the formyl moiety was metabolized by mouse liver microsomes in the presence of NADPH to a species which was bound covalently to microsomal protein. This covalent binding in vitro was abolished in the presence of glutathione (Pearson et al 1987a). Drug-derived radioactivity was incorporated into or bound to hepatic proteins also when [14C]NMF was administered to mice (Pearson et al 1987a). Intraperitoneal injection of NMF (200 mg/kg) in mice caused depletion of the liver glutathione pools by 79% 2 h after administration (Pearson et al 1987b). Incubation of isolated mouse hepatocytes with 7 mM NMF, which was the peak plasma concentration achieved after administration of 400 mg/kg in mice (Brindley et al 1982), led to a significant decrease in intracellular glutathione levels without an increase in glutathione disulfide (Whitby et al 1984b). Similarly, concentrations of NMF in the 0.1 M range caused glutathione depletion in cultures of human colon carcinoma cells (Cordeiro and Savarese, 1984, Cordeiro and Savarese, 1986). This depletion was accompanied by inhibition of cell growth.

Purification Methods

Dry it over molecular sieves for 2days, then distil it under reduced pressure through a column packed with glass helices. Fractionally crystallise it by partial freezing and the solid portion is distilled in a vacuum. [Beilstein 4 IV 170.]

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