Methoxyamine is the

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

with the formula CH₃ONH₂. Also called ''O''-methylhydroxylamine, it a colourless volatile liquid that is soluble in polar organic solvent and in water. It is a derivative of

hydroxylamine Hydroxylamine is an inorganic compound with the formula . The material is a white crystalline, hygroscopic compound.Greenwood and Earnshaw. ''Chemistry of the Elements.'' 2nd Edition. Reed Educational and Professional Publishing Ltd. pp. 431–43 ...

with the

hydroxyl In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...

hydrogen replaced by a

methyl In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula . In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in many ...

group. Alternatively, it can be viewed as a derivative of

methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical and the simplest aliphatic alcohol, with the formula C H3 O H (a methyl group linked to a hydroxyl group, often abbreviated as MeOH). It is a ...

with the hydroxyl hydrogen replaced by an

amino In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent s ...

group. It is an isomer of N-methylhydroxylamine and

aminomethanol Aminomethanol is the amino alcohol with the chemical formula of H2NCH2OH. With an amino group and an alcohol group on the same carbon atom, the compound is also an hemiaminal. In aqueous solution, methanolamine exists in equilibrium with formald ...

. It decomposes in an exothermic reaction (-56 kJ/mol) to

methane Methane ( , ) is a chemical compound with the chemical formula (one carbon atom bonded to four hydrogen atoms). It is a group-14 hydride, the simplest alkane, and the main constituent of natural gas. The relative abundance of methane on Eart ...

and

azanone Nitroxyl (common name) or azanone (IUPAC name) is the chemical compound HNO. It is well known in the gas phase. Nitroxyl can be formed as a short-lived intermediate in the solution phase. The conjugate base, NO−, nitroxide anion, is the redox re ...

unless stored as a hydrochloride salt.

Synthesis

Methoxyamine is prepared via ''O''-alkylation of hydroxylamine derivatives. For example, it is obtained by ''O''-methylation of

acetone oxime Acetone oxime (acetoxime) is the organic compound with the formula (CH3)2CNOH. It is the simplest example of a ketoxime. It is a white crystalline solid that is soluble in water, ethanol, ether, chloroform, and ligroin. It is used as a reagent ...

followed by hydrolysis of the ''O''-methylated oxime: :(CH₃)₂CNOCH₃ + H₂O → (CH₃)₂CO + H₂NOCH₃ The other broad method involves

ysis of hydroxylamine sulfonates: :H₂NOSO₃⁻ + CH₃OH → H₂NOCH₃ + HSO₄⁻

Reactions

Analogous to the behavior of hydroxylamine, methoxyamine condenses with ketones and aldehydes to give imines. Methoxyamine is used as a

synthon In retrosynthetic analysis, a synthon is a hypothetical unit within a target molecule that represents a potential starting reagent in the retroactive synthesis of that target molecule. The term was coined in 1967 by E. J. Corey. He noted in 19 ...

for NH₂⁺. It undergoes deprotonation by

methyl lithium Methyllithium is the simplest organolithium reagent with the empirical formula CH3Li. This s-block organometallic compound adopts an oligomeric structure both in solution and in the solid state. This highly reactive compound, invariably used in s ...

to give CH₃ONHLi. This ''N''-lithio derivative is attacked by organolithium compounds to give, after hydrolysis, amines: : H₂NOCH₃ + CH₃Li → LiHNOCH₃ + CH₄ : LiHNOCH₃ + RLi → RNHLi + LiOCH₃ : RNHLi + H₂O → RNH₂ + LiOH

Uses

Methoxyamine has potential medicinal uses. Itcovalently binds to apurinic/apyrimidinic (AP) DNA damage sites and inhibits base excision repair (BER), which may result in an increase in DNA strand breaks and apoptosis.This agent may potentiate the anti-tumor activity of alkylating agents.NCI
/ref> Methoxyamine Examples of drugs incorporating the methoxyamine unit are

brasofensine Brasofensine (NS-2214, BMS-204756) is a phenyltropane that had been under development by Bristol-Myers Squibb for the treatment of Parkinson's and Alzheimer's diseases. In animal models of Parkinson's disease, brasofensine was effective in stimu ...

and

gemifloxacin Gemifloxacin mesylate (trade name Factive, Oscient Pharmaceuticals) is an oral broad-spectrum quinolone antibacterial agent used in the treatment of acute bacterial exacerbation of chronic bronchitis and mild-to-moderate pneumonia. Vansen Ph ...

References

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External links

Sigma-Aldrich Methoxyamine Hydrochloride
Hydroxylamines