1518-89-4

Basic information

• Product Name: l-p-Hydroxyamphetamine
• Synonyms: (-)-p-[(R)-2-Aminopropyl]phenol;4-[(2R)-2-Aminopropyl]phenol;4-[(R)-2-Aminopropyl]phenol;l-p-Hydroxyamphetamine;p-Hydroxy-l-amphetamine
• CAS NO: 1518-89-4
• Molecular Formula: C₉H₁₃NO
• Molecular Weight: 0
• Mol File: 1518-89-4.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: l-p-Hydroxyamphetamine(CAS DataBase Reference)
• NIST Chemistry Reference: l-p-Hydroxyamphetamine(1518-89-4)
• EPA Substance Registry System: l-p-Hydroxyamphetamine(1518-89-4)

Safety Data

• Hazardous Substances Data: 1518-89-4(Hazardous Substances Data)

Usage

Description

l-p-Hydroxyamphetamine, also known as (R)-4-(2-Aminopropyl)phenol, is a chemical compound with a unique structure that features a phenol group and an aminopropyl side chain. It is primarily used as a reagent in various research applications, particularly in the field of pharmaceuticals and drug metabolism.

Uses

Used in Pharmaceutical Research:
l-p-Hydroxyamphetamine is used as a reagent for the investigation of biotransformation products and metabolism of various drugs. It plays a crucial role in the multivariate optimization of zebrafish water tank models, which are essential for understanding the effects of different substances on aquatic organisms and their potential use in doping control analysis.
Used in Doping Control Analysis:
In the field of sports and anti-doping, l-p-Hydroxyamphetamine is employed for the analysis of biotransformation products and metabolism of specific drugs such as sibutramine, selegiline, JWH-073, and hexareline. This application helps in detecting the presence of these substances in athletes and ensuring fair competition by preventing the use of performance-enhancing drugs.
Used in Drug Metabolism Studies:
l-p-Hydroxyamphetamine is also utilized in the study of drug metabolism, which is vital for understanding how drugs are broken down and processed within the body. This knowledge can be applied to improve drug design, efficacy, and safety, ultimately leading to better pharmaceutical treatments for various medical conditions.

Upstream product

• 144556-91-2 N-[(R)-2-(4-hydroxy-phenyl)-1-methyl-ethyl]-toluene-4-sulfonamide 
• 64-13-1 2-amino-1-(4-methyoxyphenyl)propane 
• 1351781-81-1 C₁₂H₁₇NO₃ 
• 3938-96-3 ethyl 2-methoxyacetate 
• 103-86-6 p-hydroxyamphetamine 
• 17354-63-1 4-(2-nitro-propenyl)-anisole 
• 123-11-5 4-methoxy-benzaldehyde 
• 735231-40-0 C₁₇H₂₁NO 
• 770-39-8 4-methoxyphenylacetone 

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.

Enzymatic enantiomeric resolution of phenylethylamines structurally related to amphetamine

Both enantiomers of several phenylethylamines, structurally related to amphetamine, have been prepared in good yields and excellent enantiomeric purity by enzymatic kinetic resolution using CAL-B and ethyl methoxyacetate as the acyl donor. In the case of the 4-hydroxyderivative of amphetamine (compound 4i), the S enantiomer racemized possibly in a dynamic kinetic resolution (DKR) under the enzymatic conditions used. The Royal Society of Chemistry 2011.