{{distinguish|N-Methylhydroxylamine}} {{Chembox | ImageFile = Methoxyamine.svg | ImageSize = 150px | ImageName = Methoxyamine | ImageFile1 = Methoxyamine-3D.jpg | ImageSize1 = 200px | ImageName1 = Methoxyamine | PIN = ''O''-Methylhydroxylamine<ref>{{cite book |author=International Union of Pure and Applied Chemistry |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=The Royal Society of Chemistry |pages=994 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}</ref> | OtherNames = Methoxylamine; (Aminooxy)methane |Section1={{Chembox Identifiers | CASNo = 67-62-9 | CASNo_Ref = {{cascite|correct|CAS}} | ChEMBL = 1213633 | ChemSpiderID = 3970 | EC_number = 200-660-1 | DrugBank = DB06328 | PubChem = 4113 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 9TZH4WY30J | InChI = 1S/CH5NO/c1-3-2/h2H2,1H3 | InChIKey = GMPKIPWJBDOURN-UHFFFAOYSA-N | SMILES = CON }} |Section2={{Chembox Properties | C=1 | N=1 | O=1 | H=5 | Appearance = Colorless liquid | Odor = Ammoniacal | BoilingPtC = 48.1 <ref name=Kokko>{{cite book |last1=Kokko |first1=Bruce J. |last2=Edmondson |first2=Scott D. |chapter=O -Methylhydroxylamine |title=Encyclopedia of Reagents for Organic Synthesis |date=14 March 2008 |pages=rm192m.pub2 |doi=10.1002/047084289X.rm192m.pub2|isbn=978-0471936237 }}</ref> | MeltingPtC = -86.4<ref name=Kokko/> | Solubility = Miscible | RefractIndex = 1.4164 | VaporPressure = 297.5 mmHg at 25°C }} |Section7={{Chembox Hazards | GHS_ref=<ref>{{cite web |title=O-Methylhydroxylamine |url=https://pubchem.ncbi.nlm.nih.gov/compound/4113#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref> | GHSPictograms = {{GHS05}}{{GHS07}} | GHSSignalWord = Danger | HPhrases = {{H-phrases|302|312|314|332}} | PPhrases = {{P-phrases|260|261|264|264+265|270|271|280|301+317|301+330+331|302+352|302+361+354|304+340|305+354+338|316|317|321|330|362+364|363|405|501}} | ExternalSDS = [http://datasheets.scbt.com/sc-257710.pdf Santa Cruz] (HCl) | NFPA-H = 3 | NFPA-F = 1 | NFPA-R = 1 | NFPA-S = }} }}
'''Methoxyamine''' is the organic compound with the formula CH<sub>3</sub>ONH<sub>2</sub>. Also called '''''O''-methylhydroxylamine''', it is 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, an alkoxyamine. 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.
==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:<ref>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.</ref> :(CH<sub>3</sub>)<sub>2</sub>CNOCH<sub>3</sub> + H<sub>2</sub>O → (CH<sub>3</sub>)<sub>2</sub>CO + H<sub>2</sub>NOCH<sub>3</sub>
The other broad method involves methanolysis of hydroxylamine sulfonates: :H<sub>2</sub>NOSO<sub>3</sub><sup>−</sup> + CH<sub>3</sub>OH → H<sub>2</sub>NOCH<sub>3</sub> + HSO<sub>4</sub><sup>−</sup>
Commercial products are usually the hydrochloride salt.<ref name=Kokko/>
==Reactions== Analogous to the behavior of hydroxylamine, methoxyamine condenses with ketones and aldehydes to give imines.
Methoxyamine is used as a synthon for NH<sub>2</sub><sup>+</sup>. It undergoes deprotonation by methyl lithium to give CH<sub>3</sub>ONHLi. This ''N''-lithio derivative is attacked by organolithium compounds to give, after hydrolysis, amines:<ref>{{cite book|doi=10.1002/047084289X.rm192m.pub2|chapter=O-Methylhydroxylamine |title=Encyclopedia of Reagents for Organic Synthesis |year=2008 |last1=Kokko |first1=Bruce J. |last2=Edmondson |first2=Scott D. |isbn=978-0471936237 }}</ref> : H<sub>2</sub>NOCH<sub>3</sub> + CH<sub>3</sub>Li → LiHNOCH<sub>3</sub> + CH<sub>4</sub> : LiHNOCH<sub>3</sub> + RLi → RNHLi + LiOCH<sub>3</sub> : RNHLi + H<sub>2</sub>O → RNH<sub>2</sub> + LiOH
==Uses== Methoxyamine has potential medicinal uses. It 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.This agent may potentiate the anti-tumor activity of alkylating agents.<ref name=NCI>[http://www.cancer.gov/drugdictionary?cdrid=599836 NCI]</ref>
Examples of drugs incorporating the methoxyamine unit are brasofensine and gemifloxacin.
==References== {{reflist}}
==External links== * [http://www.sigmaaldrich.com/catalog/product/aldrich/226904 Sigma-Aldrich Methoxyamine Hydrochloride]
Category:Hydroxylamines Category:Foul-smelling chemicals Category:Methoxy compounds