Hydrazinecarboxaldehyde, 1-methyl-

HCID 12962CAS 758-17-8

Basic information

Standard SMILES
CN(N)C=O
InChIKey
RSFOTOSOKJMMCB-UHFFFAOYSA-N
Molecular formula
C2H6N2O
Average molar mass
74.08 g/mol
Monoisotopic mass
74.04801281

Overview

structure

Names & identifiers

Preferred name
Hydrazinecarboxaldehyde, 1-methyl-
IUPAC
N-amino-N-methylformamide
English name
N-methyl-N-formylhydrazine
Molecular formula
C2H6N2O
Molecular weight
74.08

Names & synonyms

N-METHYL-N-FORMYLHYDRAZINE758-17-8N-Formyl-N-methylhydrazineMethylformylhydrazineHydrazinecarboxaldehyde, 1-methyl-Formic acid, 1-methylhydrazide1-Methyl-1-formylhydrazide2-Methyl-2-formylhydrazineFormic acid, methylhydrazideHydrazine, 1-formyl-1-methyl-3L13R06H7DNSC-122452
Show more names
1-Methyl-1-formylhydrazidMFH1-MethylformhydrazidN-MethylformhydrazideN-METHYL-N-FORMYLHYDRAZIDE
DTXSID2020840RefChem:163756DTXCID60840N-MethylformohydrazideN-amino-N-methylformamide1-Methyl-1-formylhydrazine1-Methylformylhydrazine1-formyl-1-methylhydrazine

Database identifiers

CAS
758-17-8
PubChem CID
12962
DTXSID
DTXSID2020840
UNII
3L13R06H7D
EC Number
970-987-9
Nikkaji
J34.716G

Properties

Computed structural properties

XLogP
-1
Topological polar surface area
46.3 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
5

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Hydrazides

Physicochemical properties

Melting point
219 · 219-222 °C(Solv: ethanol (64-17-5))
Boiling point
131.34 °C · 131.34°C (rough estimate)
Density
1.0968 · 1.0968 (rough estimate)
refractive index
1.4368 · 1.4368 (estimate)
storage temp.
2 · 2-8°C, protect from light, stored under nitrogen
solubility
Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P203, P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P318, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazards SummaryEmergency treatment: Hydrazines; Hydrazines can cause severe eye damage. They can cause seizures, liver injury, hemolysis, and delayed pulmonary edema. [HSDB] Oral LD50 (mouse) = 118 mg/kg; [RTECS]
Special Reports · 2 items

Toth B; Teratogenic hydrazines: a review; In Vivo Jan-Feb 7 (1): 101-10 (1993). The review summarizes the results of 30 hydrazines, which were studied in humans and in six animal species for teratogenic activities.

Michelot D, Toth B; Poisoning by Gyromitra esculenta--a review; J Appl Toxicol 11 (4): 235-43 (1991). Gyromitra esculenta and a few other mushrooms have caused severe poisonings and even deaths in humans.

Hazard Classes and CategoriesAcute Tox. 3 (100%)

Safety & protection

Disposal Methods · 1 item

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Preventive Measures · 2 items

Inhalation of salt dusts should be avoided. /Hydrazine & derivatives/

Engineering controls, such as process enclosure or local exhaust ventilation, shall be used when needed to keep concentrations of airborne hydrazines within acceptable levels. Ventilation systems shall be designed to prevent accumulation or recirculation of airborne hydrazines in the workplace environment and to remove hydrazines from the breathing zone of workers. /Hydrazines/

Personal Protective Equipment (PPE) · 3 items

All systems or equipment containing the hydrazines shall be designed to minimize the possibility of vapor or aerosol inhalation, skin or eye contact, and spill or leaks; such as full face shields, goggles, and full body protection clothing, including gloves and boots. /Hydrazines/

... VINYL COATED HAND PROTECTION, NATURAL OR RECLAIMED RUBBER PROTECTION, RUBBER APRONS, AND PLASTIC EYE AND FACE PROTECTION ... USED WHEN WORKING WITH SMALL QUANTITIES. WHERE POSSIBILITY OF GROSS SPLASHING EXISTS, FULL PROTECTIVE CLOTHING MADE OF RUBBER, NEOPRENE OR VINYL-COATED MATERIALS SHOULD BE WORN. FOR RESPIRATORY PROTECTION IN SITUATIONS WHERE RECOMMENDED TOLERANCE LIMITS ... EXCEEDED, RESPIRATORY PROTECTIVE EQUIPMENT SUCH AS APPROVED CANISTERS OR A GAS MASK OR SELF CONTAINED BREATHING APPARATUS MUST BE USED. /HYDRAZINE & DERIVATIVES/

All systems or equipment containing the hydrazines shall be designed to minimize the possibility of vapor or aerosol inhalation, skin or eye contact, and spill or leaks; such as full face shields, goggles, and full body protection clothing, including gloves and boots. /Hydrazines/

Toxicology

InteractionsSINGLE SC INJECTIONS OF N-METHYL-N-FORMYLHYDRAZINE (MFH) WERE GIVEN ALONE & JOINTLY WITH PYRIDOXINE HYDROCHLORIDE TO SWISS MICE. THE TOXIC SYMPTOMS CAUSED BY MFH WERE ONLY SLIGHTLY INHIBITED BY THIS VITAMIN.
Adverse EffectsNeurotoxin - Other CNS neurotoxin
Natural Pollution SourcesN-METHYL-N-FORMYLHYDRAZINE IS A STABLE CONSTITUENT OF THE EDIBLE FALSE MOREL MUSHROOM GYROMITRA ESCULENTA.
Non-Human Toxicity Excerpts · 5 items

SEPARATE ADMIN OF 0.005-0.00025% N-METHYL-N-FORMYLHYDRAZINE (MFH) IN DRINKING WATER TO 6-WK-OLD RANDOMLY BRED SWISS MICE FOR REMAINDER OF THEIR LIFETIME INDUCED LUNG NEOPLASMS. AT HIGH DOSE, 64% OF FEMALES & 48% OF MALES DEVELOPED LUNG NEOPLASMS, WHILE CORRESPONDING TUMOR INCIDENCES AT LOWER DOSE LEVEL WERE 62% IN FEMALES & 54% IN MALES. IN THE UNTREATED CONTROLS, LUNG TUMOR INCIDENCES WERE 29% IN FEMALES & 19% IN MALES. THE LESIONS WERE CLASSIFIED AS ADENOMAS & ADENOCARCINOMAS OF THE LUNGS.

SOLUTIONS OF 0.002 & 0.001% N-METHYL-N-FORMYLHYDRAZINE (MFH) WERE ADMIN SEPARATELY DAILY IN DRINKING WATER TO 6-WK-OLD RANDOMLY BRED SWISS MICE FOR LIFE. TUMORS WERE OBSERVED IN THE LUNGS, BLOOD VESSELS, LIVER & GALL BLADDER. 0.002% SOLN GAVE RISE TO TUMORS OF THE ABOVE TISSUES IN INCIDENCES OF 76, 27, 28 & 11% RESPECTIVELY, WHILE 0.001% SOLN WAS 75, 23, 7 & 6%. HISTOPATHOLOGICALLY, THE NEOPLASMS WERE ADENOMAS & ADENOCARCINOMAS OF LUNGS, ANGIOMAS & ANGIOSARCOMAS OF BLOOD VESSELS, BENIGN HEPATOMAS, LIVER CELL CARCINOMAS & ADENOMAS & ADENOCARCINOMAS OF GALL BLADDER.

SINGLE SC INJECTIONS OF N-METHYL-N-FORMYLHYDRAZINE WERE GIVEN TO RANDOMLY BRED MICE. THE FEMALES RECEIVED 180 MUG/G, WHILE 2 GROUPS OF MALES WERE TREATED WITH EITHER 120 OR 100 MUG/G. THE TREATMENT RESULTED IN INDUCTION OF TUMORS OF LUNGS WITH AN INCIDENCE OF 40% IN THE FEMALES. IN MALES TREATED WITH THE HIGHER AND LOWER DOSES, THE INCIDENCES OF PREPUTIAL GLAND TUMORS WERE 12 AND 12%, RESPECTIVELY. HISTOPATHOLOGY, THE TUMORS WERE CLASSIFIED AS ADENOMAS AND ADENOCARCINOMAS OF LUNGS, SQUAMOUS CELL PAPILLOMAS, AND CARCINOMAS OF PREPUTIAL GLANDS.

MFH WAS ADMIN IN DRINKING WATER AS A 0.0078% SOLN TO RANDOMLY BRED SYRIAN GOLDEN HAMSTERS FOR LIFE BEGINNING @ 6 WK OF AGE. THE TREATMENT GAVE RISE TO BENIGN AND MALIGNANT LIVER CELL TUMORS, MALIGNANT HISTIOCYTOMAS AND TUMORS OF THE GALL BLADDER AND BILE DUCTS. THE TUMOR INCIDENCE IN THESE 4 TREATED TISSUES WAS 43, 34, 11 AND 8%, RESPECTIVELY, WHILE IN UNTREATED CONTROLS IT WAS 0%.

For more Non-Human Toxicity Excerpts (Complete) data for N-METHYL-N-FORMYLHYDRAZINE (14 total), please visit the HSDB record page.

Antidote and Emergency Treatment · 5 items

Specific treatment for exposure consists of thorough washing of all exposed skin areas with soap and water, copious irrigation of the eyes, and prompt removal of the patient from the source of exposure. /Hydrazines/

After inhalation, observation for progressive respiratory distress is necessary. Chest X-ray and arterial blood gases should be monitored. Administration of oxygen, intubation, and assisted ventilation may become necessary. Pneumonia and bronchitis need to be excluded. /Hydrazines/

If ingestion has occurred, gastric lavage or emesis should be followed by administration of activated charcoal and catharsis. Emesis is most effective if it is initiated within 30 minutes of ingestion. /Hydrazines/

Pyridoxine may be antidotal. The suggested dose is 25 mg per kg with half of this dose given intramuscularly and two-thirds given IV over 3 hours. Seizures should be controlled with diazepam, phenytoin, or phenobarbital. Blood sugar levels should be monitored for severe hypoglycemia, which may appear with or without preceding significant hyperglycemia. The patient should be observed for evidence of intravascular hemolysis, methemoglobinemia, and consequent deterioration of renal function. Patients who are symptomatic or who demonstrate a methemoglobin level greater than 30 per cent should be treated with methylene blue 1 to 2 mg per kg slowly IV every 4 hours as needed. Improvement is dramatic if diagnosis is correct. Liver function should be monitored because hydrazines are known hepatotoxins. /Hydrazines/

Elimination is enhanced by forced diuresis and acidification of the urine. Hemodialysis and peritoneal dialysis should be effective, but insufficient human data exist on the use of these modalities. Treatment is otherwise symptomatic and supportive. /Hydrazines/

Safety data

Toxicity
LD50 oral in mouse: 118mg/kg
Hazardous Substances Data
758-17-8(Hazardous Substances Data)

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 5 items

N-METHYL-N-FORMYLHYDRAZINE (MFH) IS FORMED BY HYDROLYSIS FROM GYROMITRIN, THE MAIN TOXIN OF THE EDIBLE MUSHROOM GYROMITRA ESCULENTA. CYTOCHROME P-450 MEDIATES THE OXIDN OF MFH TO HYDROXYLAMINE DERIV & FURTHER TO NITROSAMIDE. THIS NITROSAMIDE FORMATION MAY BE THE REASON FOR THE KNOWN HEPATOCARCINOGENICITY OF METHYLFORMYLHYDRAZINE.

AFTER ORAL APPLICATION OF THE EDIBLE MUSHROOM POISON GYROMITRIN A TIME AND DOSE DEPENDENT DECR OF CYTOCHROME P-450 WAS FOUND IN RAT LIVER MICROSOMES. THE MAXIMAL DECR TO ABOUT 50-60% OF THE CONTROL (AFTER 200 MG/KG, 80% OF LD50) WAS OBSERVED 8-12 HR AFTER APPLICATION, A NORMALIZATION OCCURRED AFTER 48 HR. COMPARABLE RESULTS WERE OBTAINED AFTER APPLICATION OF N-METHYL-N-FORMYLHYDRAZINE WHICH IS FORMED FROM GYROMITRIN RAPIDLY BY HYDROLYSIS.

MONOMETHYLHYDRAZINE, BUT NOT N-METHYL-N-FORMYLHYDRAZINE (MFH), A MUSHROOM POISON, CAN BE OXIDIZED BY THE WEAK OXIDANT 2,6-DICHLOROPHENOLINDOPHENOL. MFH MUST BE ACTIVATED IN VIVO INTO TOXIC METABOLITES WHICH ARE ULTIMATELY RESPONSIBLE FOR THE KNOWN HIGH CARCINOGENICITY OF MFH.

GYROMITRIN IS RAPIDLY HYDROLYSED, NON-ENZYMATICALLY, BOTH IN VITRO AND IN VIVO, TO ACETALDEHYDE AND N-METHYL-N-FORMYLHYDRAZINE; THE LATTER IS HYDROLYSED UNDER PHYSIOLOGICAL CONDITIONS AT A MUCH SLOWER RATE TO FORM N-METHYLHYDRAZINE AND FORMIC ACID. AT 37 °C, 1 MM GYROMITRIN WAS HYDROLYSED TO N-METHYLHYDRAZINE, WITH A HALF-LIFE OF 122 MIN AT PH 2; WHEREAS AT PH 3 ONLY 9% APPEARED AS N-METHYLHYDRAZINE AFTER 72 HR.

N-METHYLHYDRAZINE WAS...FOUND IN THE MOUSE STOMACH AFTER ORAL ADMIN OF 4 MG/ANIMAL GYROMITRIN. GYROMITRIN, N-METHYLHYDRAZINE AND N-METHYL-N-FORMYLHYDRAZINE WERE FOUND IN THE PERITONEAL FLUID OF MICE 3 HR AFTER ORAL ADMIN OF 9 MG GYROMITRIN.

Uses & manufacturing

UsesFound in the edible mushroom Gyromitra esculenta (false morel) and hydrolyzed to N-Methylhydrazine and formic acid; [HSDB]

Applications

UsesN-Methyl-N-formylhydrazine is a substituent used in the synthesis of Marbofloxacin (M197000), a fluorinated quinolone antibacterial agent.

Suppliers45 total

青岛鼎新海诺商贸有限公司18661607483
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
上海炎泽化工有限公司15345144255 19975051755 · [email protected]
济南润丰生物科技有限公司15628881692 · [email protected]
安耐吉化学&3A(安徽泽升科技有限公司)021-58432009 400-005-6266 · [email protected]

Related reactions

12 records

Linked notes

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