1518-86-1

Basic information

• Product Name: Hydroxyamphetamine
• Synonyms: Hydroxyamphetamine;4-hydroxyamphetamine;Paredrinex;Pulsoton;α-Methyramine;4-(2-azanylpropyl)phenol
• CAS NO: 1518-86-1
• Molecular Formula: C9H13NO
• Molecular Weight: 0
• EINECS: 203-152-8
• Mol File: 1518-86-1.mol
• Article Data: 19

Chemical Properties

• Melting Point: 125-126°
• Boiling Point: 273.23°C (rough estimate)
• Flash Point: 122.7°C
• Appearance: /
• Density: 1.0406 (rough estimate)
• Vapor Pressure: 0.0024mmHg at 25°C
• Refractive Index: 1.5270 (estimate)
• PKA: pKa 9.6 (Uncertain)
• CAS DataBase Reference: Hydroxyamphetamine(CAS DataBase Reference)
• NIST Chemistry Reference: Hydroxyamphetamine(1518-86-1)
• EPA Substance Registry System: Hydroxyamphetamine(1518-86-1)

Safety Data

• Hazardous Substances Data: 1518-86-1(Hazardous Substances Data)

Usage

General Description

Hydroxyamphetamine is an effective,indirect-acting sympathomimetic drug. It differs from amphetaminein the presence of p-OH group and so it has littleor no CNS-stimulating action. It is used to dilate the pupilfor diagnostic eye examinations and for surgical procedureson the eye. It is sometimes used with cholinergic blockingdrugs like atropine to produce a mydriatic effect, which ismore pronounced than that produced by either drug alone.

Veterinary Drugs and Treatments

Hydroxyamphetamine is an indirectly acting sympathomimetic which is used to diagnose Cranial Nerve III denervation syndromes such as Horner’s Syndrome. Hydroxyamphetamine stimulates release of norepinephrine from postganglionic neurons and therefore amplifies pupil dilation response in hypersensitive, denerved neurons.

InChI:InChI=1/C9H13NO/c1-7(10)6-8-2-4-9(11)5-3-8/h2-5,7,11H,6,10H2,1H3

Upstream product

• 64-13-1 2-amino-1-(4-methyoxyphenyl)propane 
• 60-15-1 2-amino-1-phenylpropane 
• 17354-63-1 4-(2-nitro-propenyl)-anisole 
• 4397-53-9 p-benzyloxybenzaldehyde 
• 7176-38-7 1-(4-Benzyloxyphenyl)-2-nitro-1-propen 
• 7176-39-8 2-(4-benzyloxy-phenyl)-1-methyl-ethylamine 
• 3938-96-3 ethyl 2-methoxyacetate 
• 103-86-6 p-hydroxyamphetamine 
• 123-11-5 4-methoxy-benzaldehyde 
• 735231-40-0 C₁₇H₂₁NO 
• 770-39-8 4-methoxyphenylacetone 
• 1351781-81-1 C₁₂H₁₇NO₃ 
• 144556-91-2 N-[(R)-2-(4-hydroxy-phenyl)-1-methyl-ethyl]-toluene-4-sulfonamide 
• 37629-51-9 1-methoxy-4-((E)-2-nitroprop-1-enyl)benzene 

Downstream Products

• 103153-58-8 4-[2-(1-methyl-2-phenyl-ethylamino)-propyl]-phenol 
• 62401-66-5 p-Hydroxy-fenetyllin 
• 1241224-85-0 C₁₉H₂₅N₃O₂ 
• 1241565-96-7 C₁₈H₃₀N₂O₂ 
• 1281135-71-4 1-[2-(4-hydroxy-phenyl)-1-methyl-ethyl]-3-(2-thiophen-2-yl-ethyl)-urea 
• 27566-05-8 4-(2-(benzylamino)propyl)phenol 
• 3673-98-1 rac. 2-(4-Hydroxy-phenyl)-1-methyl-2'-phenoxy-diaethylamin 
• 60677-79-4 (2,6-Dichloro-4-{1-hydroxy-2-[2-(4-hydroxy-phenyl)-1-methyl-ethylamino]-ethyl}-phenyl)-carbamic acid ethyl ester 

Relevant articles and documents

Iterative Alanine Scanning Mutagenesis Confers Aromatic Ketone Specificity and Activity of L-Amine Dehydrogenases

Direct reductive amination of prochiral ketones catalyzed by amine dehydrogenases is attractive in the synthesis of active pharmaceutical ingredients. Here, we report the protein engineering of L-Bacillus cereus amine dehydrogenase to allow reactivity on synthetically useful aromatic ketone substrates using an iterative, multiple-site alanine scanning mutagenesis approach. Mutagenesis libraries based on molecular docking, iterative alanine scanning, and double-proximity filter approach significantly expand the scope of active pharmaceutical ingredients relevant building blocks. The eventual quintuple mutant (A115G/T136A/L42A/V296A/V293A) showed reactivity toward aromatic ketones 12 a (5-phenyl-pentan-2-one) and 13 a (6-phenyl-hexan-2-one), which have not been reported to serve as targets of reductive amination by currently available amine dehydrogenases. Docking simulation and tunnel analysis provided valuable insights into the source of the acquired specificity and activity.

Improved synthetic method of (R)-1-aryl-2-propylamine

The invention provides an improved synthetic method of (R)-1-aryl-2-propylamine. The improved synthetic method comprises the following steps of: adopting 1-arylacetone as a raw material, adding (R)-1-phenylethylamine, carrying out reductive amination reaction with hydrogen under a common action of a Lewis acid additive and a transitional metal hydrogenation catalyst; carrying out Pd/C catalytic hydrogenation on an obtained intermediate to remove phenethyl on nitrogen and thus obtaining (R)-1-aryl-2-propylamine. The improved synthetic method provided by the invention has the beneficial effectsthat the operation is simple, the adopted Lewis acid additive is low in cost and easy in obtaining, the yield and the enantioselectivity of a product are high, and the application value for industrialsynthesis of (R)-1-aryl-2-propylamine is very high.

MOF-derived cobalt nanoparticles catalyze a general synthesis of amines

The development of base metal catalysts for the synthesis of pharmaceutically relevant compounds remains an important goal of chemical research. Here, we report that cobalt nanoparticles encapsulated by a graphitic shell are broadly effective reductive amination catalysts. Their convenient and practical preparation entailed template assembly of cobaltdiamine- dicarboxylic acid metal organic frameworks on carbon and subsequent pyrolysis under inert atmosphere.The resulting stable and reusable catalysts were active for synthesis of primary, secondary, tertiary, and N-methylamines (more than 140 examples).The reaction couples easily accessible carbonyl compounds (aldehydes and ketones) with ammonia, amines, or nitro compounds, and molecular hydrogen under industrially viable and scalable conditions, offering cost-effective access to numerous amines, amino acid derivatives, and more complex drug targets.