390-28-3

Basic information

• Product Name: methoxamine
• Synonyms: 2-Amino-1-(2,5-dimethoxyphenyl)propan-1-ol;a-(1-Aminoethyl)-2,5-dimethoxybenzyl alcohol;Benzenemethanol, a-(1-aminoethyl)-2,5-dimethoxy- (9CI);Benzyl alcohol, a-(1-aminoethyl)-2,5-dimethoxy- (8CI);Methoxamine (6CI);Methoxamin;α-(1-Aminoethyl)-2,5-dimethoxybenzenemethanol;α-(1-Aminoethyl)-2,5-dimethoxybenzyl alcohol
• CAS NO: 390-28-3
• Molecular Formula: C₁₁H₁₇NO₃
• Molecular Weight: 211.26
• EINECS: 206-867-3
• Mol File: 390-28-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 85-86 °C
• Boiling Point: 368.4°Cat760mmHg
• Flash Point: 176.6°C
• Appearance: /
• Density: g/cm³
• PKA: 11.87±0.45(Predicted)
• CAS DataBase Reference: methoxamine(CAS DataBase Reference)
• NIST Chemistry Reference: methoxamine(390-28-3)
• EPA Substance Registry System: methoxamine(390-28-3)

Safety Data

• Hazardous Substances Data: 390-28-3(Hazardous Substances Data)

Usage

Originator

Vasoxyl ,Burroughs-Wellcome,US,1949

Manufacturing Process

2,5-Dimethoxypropiophenone is treated in absolute ether with methyl nitrite and hydrogen chloride. The hydrochloride of 2,5-dimethoxy-αisonitrosopropiophenone crystallizes out of the solution. It is removed, the base is liberated and crystallized from benzene-heptane forming yellow leaflets that melt at about 97° to 98°C. This isonitrosoketone is dissolved in absolute alcohol containing an excess of hydrogen chloride and is hydrogenated with palladized charcoal, yielding β-(2,5-dimethoxyphenyl)-βketoisopropylamine hydrochloride, a salt that melts at about 176°C with decomposition. 12.3 g (1/20 mol) of β-(2,5-dimethoxyphenyl)-β-ketoisopropylamine hydrochloride (MP 176°C) is dissolved in 50 cc of water and hydrogenated with platinum oxide platinum black in the customary Adams-Burgess Parr apparatus. About 1/20 mol of hydrogen is absorbed, after which the solution is filtered off from the catalyst, evaporated to dryness in vacuo and recrystallized from absolute alcohol, absolute ether being added to decrease solubility. The hydrochloride is thus obtained in substantially theoretical yield. It crystallizes in plates and melts at 215°C.

Therapeutic Function

Hypertensive

InChI:InChI=1/C11H17NO3/c1-7(12)11(13)9-6-8(14-2)4-5-10(9)15-3/h4-7,11,13H,12H2,1-3H3

Upstream product

• 100619-48-5 (1RS,2RS)-2-acetylamino-1-(2,5-dimethoxy-phenyl)-propan-1-ol 
• 14367-75-0 1-Acetoxy-1-(2,5-dimethoxy-phenyl)-2-nitro-propan 
• 103565-48-6 2,5-dimethoxy-α-aminopropiophenone hydrochloride 
• 742095-47-2 (RS)-2-trifluoroacetamido-1-(2,5-dimethoxyphenyl)-1-propanone 

Downstream Products

• 68718-65-0 6c-(2,5-dimethoxy-phenyl)-5r-methyl-morpholin-3-one 
• 13699-29-1 (1R,2S)-Methoxamine 
• 36981-98-3 cis-2-(2,5-dimethoxy-phenyl)-3-methyl-morpholine 
• 68718-67-2 2r-(2,5-dimethoxy-phenyl)-4-isopropyl-3c-methyl-morpholine 
• 30275-30-0 1-phenyl-2-(p-tolyl)ethylamine 

Relevant articles and documents

Synthesis method of methoxamine hydrochloride

The invention discloses a method for synthesizing methoxamine hydrochloride, and belongs to the technical field of organic synthesis. According to the technical scheme, 2, 5-dimethoxybenzaldehyde serves as an initial raw material, 3-(2, 5-dimethoxyphenyl)-3-hydroxy-2-methylpropanamide is obtained through (a) hydrolysis after a Grignard reaction or (b) ammonolysis after a Reformatsky reaction or (c) the Reformatsky reaction, then the prepared 3-(2, 5-dimethoxyphenyl)-3-hydroxy-2-methylpropanamide is subjected to a Hofmann degradation reaction and then salified, and the 3-(2, 5-dimethoxyphenyl)-3-hydroxy-2-methylpropanamide is obtained. The methoxamine hydrochloride is obtained; according to the technical scheme, 2, 5-dimethoxybenzaldehyde which is simple and easy to obtain is adopted as a starting raw material, any one of three reaction routes of (a)-(c) can be selected to synthesize a key intermediate 3-(2, 5-dimethoxyphenyl)-3-hydroxy-2-methylpropanamide, then the key intermediate is subjected to Hofmann degradation and salification, and methoxamine hydrochloride is obtained. The provided reaction conditions are mild, the reaction process is safe and controllable, the total reaction yield is high, the purity is high, and the method can be used for large-scale production.

Patch and production method thereof

The present invention relates to a patch containing a substrate, a non-crosslinked adhesive layer (A) containing a drug laminated on one surface of the substrate and a crosslinked adhesive layer (B) laminated on the adhesive layer (A). According to the present invention, the percutaneous absorbability of the drug can be improved, and a patch free of problems such as adhesive residue and adhesive bleed can be provided.