4-(Methylnitrosoamino)butanoic acid
Basic information
- CAS
61445-55-4- Standard SMILES
CN(CCCC(=O)O)N=O- InChIKey
SJLBIPLIGYWGJV-UHFFFAOYSA-N- Molecular formula
- C5H10N2O3
- Average molar mass
- 146.14 g/mol
- Monoisotopic mass
- 146.06914219
Overview
N-nitroso-N-methyl-4-aminobutyric acid is a nitrosamine that has methyl and 3-carboxypropyl substituents. It is a tobacco-derived nitrosamino acid that is a known animal and potential human carcinogen. It induces bladder transitional cell carcinomas in rats and has recently been identified as a contaminant in certain blood pressure medications. It has a role as a carcinogenic agent, a xenobiotic metabolite, a plant metabolite and a rat metabolite. It is a monocarboxylic acid and a nitrosamine.
Names & identifiers
- Preferred name
- 4-(Methylnitrosoamino)butanoic acid
- IUPAC
- 4-[methyl(nitroso)amino]butanoic acid
- English name
- N-Nitroso-N-Methyl-4-Aminobutyric Acid
- Molecular formula
- C5H10N2O3
- Molecular weight
- 146.14
Names & synonyms
61445-55-4N-NITROSO-N-METHYL-4-AMINOBUTYRIC ACIDN-Methyl-N-(3-carboxypropyl)nitrosamine4-(Methylnitrosoamino)butanoic Acid4-(N-Nitroso-N-methylamino)butyric acidN-Nitrosomethyl-3-carboxypropylamineNNMAB7K7252TZ54CHEBI:176579RefChem:5165114-[methyl(nitroso)amino]butanoic acidNitrosomethyl-3-carboxypropylamine
Show more names
NMBAN56-004Losartan Impurity 17Losartan Impurity 41Azisartan Impurity 102Azilsartan Impurity 102Nitrosoamine MCP ImpurityRosuvastatin Impurity 186Losartan genotoxic impurity
CCRIS 11234-(methyl(nitroso)amino)butanoic acidRosuvastatin Impurity 61MFCD00869939Butanoic acid,4-(methylnitrosoamino)-UNII-7K7252TZ54nitroso-methyl-3-carboxypropylamineAS-63516
Database identifiers
- CAS
Properties
Computed structural properties
- XLogP
- 0
- Topological polar surface area
- 70 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 4
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 126
Physicochemical properties
- Melting point
- 25 °C · >25 °C
- Boiling point
- 265.74 °C · 265.74°C (rough estimate)
- Density
- 1.3394 · 1.3394 (rough estimate)
- refractive index
- 1.4954 · 1.4954 (estimate)
- storage temp.
- -20 °C · Hygroscopic, -20°C Freezer, Under Inert Atmosphere
- solubility
- Chloroform (Soluble), Dichloromethane (Slightly), Ethyl Acetate (Slightly)
- form
- Solid
- pka
- 4.57 · 4.57±0.10(Predicted)
- color
- Off-White to Yellow
- Stability
- Hygroscopic
- Major Application
- pharmaceutical (small molecules)
- InChI
- InChI=1S/C5H10N2O3/c1-7(6-10)4-2-3-5(8)9/h2-4H2,1H3,(H,8,9)
- InChIKey
- SJLBIPLIGYWGJV-UHFFFAOYSA-N
- SMILES
- C(O)(=O)CCCN(C)N=O
- FDA UNII
- 7 K7252TZ54 · 7K7252TZ54
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (75%): Toxic if swallowed [Danger Acute toxicity, oral]
P203, P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P354+P338, P317, P318, P319, P321, P330, P332+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 4 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 3 (75%)
Safety data
- wgk
- WGK 2
- Signal word
- Danger
- Symbol(GHS)
- GHS08,GHS07,GHS05,GHS06
- Storage Class
- 3 - Flammable liquids
- Hazard statements
- H351-H301-H335-H318-H315-H361
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 2
- Precautionary statements
- P264-P270-P301+P310-P321-P330-P405-P501-P280-P305+P351+P338-P310-P264-P280-P302+P352-P321-P332+P313-P362-P201-P202-P281-P308+P313-P405-P501-P201-P202-P281-P308+P313-P405-P501
Chemistry & industry
Applications
UsesN-Nitroso-N-methyl-4-aminobutyric acid EP reference standard is intended for use only as specifically prescribed in the European Pharmacopoeia. It is also used to prepare N-Nitrosamines spiking solution to detect the concentration of N-nitrosamines in active substances by liquid chromatography coupled with mass spectrometry according to the monograph 20542of European Pharmacopoeia.
Additional notes
DefinitionChEBI: N-nitroso-N-methyl-4-aminobutyric acid is a nitrosamine that has methyl and 3-carboxypropyl substituents. It is a tobacco-derived nitrosamino acid that is a known animal and potential human carcinogen. It induces bladder transitional cell carcinomas in rats and has recently been identified as a contaminant in certain blood pressure medications. It has a role as a carcinogenic agent, a rat metabolite, a xenobiotic metabolite and a plant metabolite. It is a monocarboxylic acid and a nitrosamine.
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