N-Methyl-N-nitrosoharnstoff

NMU · N-NITROSO-N-METHYLUREA · MNU · N-NITROSOMETHYLUREA · N-METHYL-N-NITROSOUREA · NMH · Nitrosomethylurea · Methylnitrosourea

https://huagongshe.com/de/chemical/12699

Molekülstruktur von N-Methyl-N-nitrosoharnstoff

Identifikatoren & physikalische Daten

CAS No.	28606-00-0
Summenformel	C2H5N3O2
Durchschnittliche Molmasse	103,08 g/mol
Monoisotopische Masse	103,0381764 g/mol
SMILES	CN(N=O)C(N)=O
InChIKey	ZRKWMRDKSOPRRS-UHFFFAOYSA-N
PubChem CID	12699
ChEMBL	CHEMBL288958
ChEBI	CHEBI:50102
EC No.	211-678-4
DTXSID	DTXSID4021006
Lokaler Name	N-Methyl-N-nitrosoharnstoff

Chemische & physikalische Eigenschaften

XLogP	0
Polarare Oberfläche (TPSA)	75,8
H-Brücken-Donoren	1
H-Brücken-Akzeptoren	3
Frei drehbare Bindungen	0
Schwere Atome	7
Formalladung	0
Komplexität	90,9
Stoffklassen	Hazardous Air Pollutants (HAPs)Nitrogen Compounds -> NitrosaminesCarcinogens
LogP (Verteilungskoeffizient)	log Kow = -0.03-0.4
Dichte	less than 1.0 (NTP, 1992)1.5048 (rough estimate)
Color/Form	Colorless or yellow plates from ethanol
Löslichkeit	less than 1 mg/mL at 64 °F (NTP, 1992)In water, 1.443X10+4 mg/l at 24 °CSoluble in waterSoluble in ethanol, etherDMSO: 125 mg/mL (1212.65 mM)14.56g/L(temperature not stated)
Decomposition	Melting point: 124 °C (decomposition).When heated to decomposition it emits toxic fumes of /nitrogen oxides/.
Schmelzpunkt	255 °F (decomposes) (NTP, 1992)123 °C119-124°C
Dampfdruck	Non-volatile (NTP, 1992)0.02 [mmHg]
Physical Description	N-nitroso-n-methylurea appears as pale yellow crystals or light yellow moist powder. (NTP, 1992)Colorless or yellow solid[HSDB]
Stability/Shelf Life	Decomposes to diazomethane in alkaline solutionsstability in aqueous solutions is pH-dependent (at 20 °C).The pure compound is sensitive to humidity and light and should be refrigerated for storage.This must be stored under refrigeration to avoid sudden decomposition after storage at ambient temp or slightly above (30 °C).... N-methyl-N-nitrosourea (MNU) ... The kinetics of N-methyl-N-nitrosourea hydrolyses are shown to be first order in N-methyl-N-nitrosourea with a steep rise in rate above pH 8. ... base-induced hydrolysis of N-methyl-N-nitrosourea is initiated by deprotonation at the carbamoyl group. The critical reactive species are shown to be the methyldiazonium ion (Me-N2+) and cyanate (NCO-). Investigations of reactions of (13CH3) N-methyl-N-nitrosourea with 2'-deoxyguanosine (dGuo) and 2'-deoxyguanosine 5'-monophosphate (dGuo-5P) showed that: a) the site of methylation of 2'-deoxyguanosine is highly pH-dependent (relatively more N-1 and O-methylation compared to N-7 occurs at higher pH)b) the principal site of methylation of 2'-deoxyguanosine 5'-monophosphate by N-methyl-N-nitrosourea is at phosphatec) incorporation of deuterium into methyl groups occurs in D20 at higher pH. Methylation of the oligonucleotide d(GT(15N)GCAC) by N-methyl-N-nitrosourea in D20 showed partial deuteriation of the N7-methyl groups of the guanines, whilst methylation by N-methyl-N-nitrosourea in water indicated no significant preference for either guanine with respect to N7-methylation.
Other Experimental Properties	Decomposes to diazomethane in alkaline solutionsstability in aqueous solutions is pH dependent: pH 4.0, half-life 125 hourspH 6.0, half-life 24 hourspH 7.0, half-life 1.2 hourspH 8.0, half-life 0.1 hoursand pH 9, half-life 0.03 hours (at 20 °C).
Siedepunkt	193.27°C (rough estimate)
Brechungsindex	1.4264 (estimate)
Lagerbedingungen	2-8°C
Aggregatzustand	Solid
pKa (Säurekonstante)	12.36±0.50(Predicted)
Farbe	Off-white to light brown
Henry-Konstante	1.9×102 mol/(m3Pa) at 25℃, Mirvish et al. (1976)
Stabilität	Stable. Flammable. Incompatible with strong oxidizing agents, strong bases, strong acids.
CAS Datenbank	684-93-5(CAS DataBase Reference)
NIST chemische Informationen	Urea, 1-methyl-1-nitroso-(684-93-5)
EPA chemische Informationen	N-Nitroso-N-methylurea (684-93-5)

Sicherheit & Vorschriften

GHS-Einstufung	DangerH228 (100%): Flammable solid [Danger Flammable solids]P203, P210, P240, P241, P264, P270, P280, P301+P316, P318, P321, P330, P370+P378, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 42 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H301: Toxic if swallowed [Danger Acute toxicity, oral]
Regulatorische Informationen	Hazard Traits - CarcinogenicityDermatotoxicityUrea, N-methyl-N-nitroso-: Does not have an individual approval but may be used under an appropriate group standardThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
DOT-Kennzeichnung	Poison
Brandgefahren	Flash point data for this chemical are not availablehowever, it is probably combustible. (NTP, 1992)
Gesundheitsgefahren	SYMPTOMS: Exposure to this compound may cause nausea, vomiting, epigastric pain, diarrhea and leukopenia. It may also cause skin rashes. Eye contact may cause damage to the retina, degeneration of pigment epithelium and destruction of the rods and outer nuclear layer leading to thinning of the whole retina and migration of pigment. Retinal atrophy and cataracts have also been reported. It may cause acetonuria.
Gefahrenübersicht	N-Nitroso-n-methylurea has been studied in mutagenicity and genetics studies and for use as a cancer chemotherapy agent. No commercial use of N-nitroso-n-methylurea is known. Acute (short-term) exposure toN-nitroso-n-methylurea in humans causes dermatitis. No information is available on the chronic (long-term), reproductive, developmental, or carcinogenic effects of N-nitroso-n-methylurea in humans or animals. Tumors have been reported in the offspring of animals treated with N-nitroso-n- methylurea during their pregnancy. Animal studies have reported tumors of the brain, spinal cord, nerves, stomach, pancreas, and kidneys from oral exposure to N-nitroso-n-methylurea. EPA has classified N- nitroso-n-methylurea as a Group B2, probable human carcinogen.Reported cause of allergic contact dermatitis

Anwendungen & Verwendung

Beschreibung

N-Nitroso-N-methylharnstoff dient zur labormäßigen Darstellung von Diazomethan. Die Substanz ist wenig haltbar und muß kühl aufbewahrt werden (bei 4 bis 8℃). Bei Temperaturen über 30℃ erfolgt Zersetzung in Isocyansäuremethylester, Stickstoff und Wasser. Bei 20℃ ist der Stoff nur einige Monate haltbar.

Beschreibung

Methylnitrosourea (MNU) is a methylated nitrosourea compound with alkylating,mutagenic, teratogenic, carcinogenic, and cytotoxic properties. The toxic effects of MNU are caused by the transfer of its methyl group to nucleobases in nucleic acids.

Verwenden

Precursor of Diazomethane. It has a cytotoxicity effect. This product contains an undetermined amount of water