2-Methyl-2-nitrosopropane

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2-Methyl-2-nitrosopropane


IUPAC name	2-Methyl-2-nitrosopropane
Other names	t-Nitrosobutane
Identifiers
Abbreviations	NMP
CAS number	[6841-96-9]
SMILES	CC(C)(C)N=O
Properties
Molecular formula	C₄H₉NO
Molar mass	87.12 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

2-Methyl-2-nitrosopropane (MNP or t-nitrosobutane, chemical formula (CH₃)₃CNO) is a spintrap. This molecule forms adducts with unstable free radicals to form a more stable paramagnetic nitroxide radical that can be detected by electron spin resonance spectroscopy. It is particularly useful for trapping carbon-centered tyrosyl radicals.^[1]

MNP is also the aerial oxidation product of t-butylhydroxylamine (NtBHA), which in turn is a hydrolysis product of phenylbutylnitrone and similar spintraps. MNP has pharmacological action, both by scavenging free radicals and possibly by releasing the messenger substance nitric oxide in the presence of light and under oxidizing conditions.^[2] Production of NtHBA and its parent spintrap MNP may account for the sometime antistroke action of the drug NXY-059.

MNP is also an efficient regulator of the radical polymerization of methyl methacrylate through the 'pseudoliving' chain mechanism.^[3]

[edit] Notes

^ see J. Biol. Chem. 271 (1996), 15498-15503
^ [1]
^ Dmitry F Grishin, Lyudmila L Semyonycheva, Elena V Kolyakina (1999). ""2-Methyl-2-nitrosopropane as a new regulator of the polymer chain growth"". Mendeleev Communications 9 (6): 250-251.