Methoxyamine

Methoxyamine is the organic compound 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 with the hydroxyl hydrogen replaced by a methyl group. Alternatively, it can be viewed as a derivative of methanol with the hydroxyl hydrogen replaced by an amino group. It is an isomer of N-methylhydroxylamine and aminomethanol. It decomposes in an exothermic reaction (-56 kJ/mol) to methane and azanone unless stored as a hydrochloride salt.

Methoxyamine
Names
IUPAC name
Methoxyamine
Other names
Methoxylamine; (Aminooxy)methane; O-Methylhydroxylamine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.000.600
UNII
Properties
CH5NO
Molar mass 47.057 g·mol−1
Appearance Colorless liquid
Odor Ammoniacal
Density 1.0003 g/mL
Melting point 42 °C (108 °F; 315 K)
Boiling point 50 °C (122 °F; 323 K)
Miscible
Vapor pressure 297.5 mmHg at 25°C
1.4164
Hazards
Safety data sheet Santa Cruz (HCl)
NFPA 704 (fire diamond)
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilHealth code 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasReactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
1
3
1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Synthesis

Methoxyamine is prepared via O-alkylation of hydroxylamine derivatives. For example, it is obtained by O-methylation of acetone oxime followed by hydrolysis of the O-methylated oxime:[1]

(CH3)2CNOCH3 + H2O → (CH3)2CO + H2NOCH3

The other broad method involves methanolysis of hydroxylamine sulfonates:

H2NOSO3− + CH3OH → H2NOCH3 + HSO4−

Reactions

Like hydroxylamine, methoxyamine forms oximes upon treatment with ketones and aldehydes.

Methoxyamine is used as a synthon for NH2+. It undergoes deprotonation by methyl lithium to give CH3ONHLi. This N-lithio derivative is attacked by organolithium compounds to give, after hydrolysis, amines:[2]

H2NOCH3 + CH3Li → LiHNOCH3 + CH4
LiHNOCH3 + RLi → RNHLi + LiOCH3
RNHLi + H2O → RNH2 + LiOH

Uses

Methoxyamine is an orally bioavailable small molecule inhibitor with potential adjuvant activity.[3] Methoxyamine covalently 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.[3] This agent may potentiate the anti-tumor activity of alkylating agents.

Examples of drugs incorporating the methoxyamine unit are brasofensine and gemifloxacin.

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References
  1. Review: Houben-Weyl, Methoden der organische Chemie, vol 10.1, p 1186. Patent: Klein, Ulrich; Buschmann, Ernst; Keil, Michael; Goetz, Norbert; Hartmann, Horst "Process for preparing O-substituted hydroxylammonium salts." Ger. Offen. to BASF, (1994), DE 4233333 A1 19940407.
  2. Bruce J. Kokko, Scott D. Edmondson "O-Methylhydroxylamine" in eEROS, 2008. doi:10.1002/047084289X.rm192m.pub2
  3. NCI
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