1693-66-9

Basic information

• Product Name: p-Hydroxy-d-amphetamine
• Synonyms: (+)-p-[(S)-2-Aminopropyl]phenol;(+)-Paredrine;4-[(2S)-2-Aminopropyl]phenol;p-Hydroxy-d-amphetamine;D-1-p-Hydroxyphenyl-2-propylamine;D-4-Hydroxyamphetamine;(S)-4-(2-AMINOPROPYL)PHENOL
• CAS NO: 1693-66-9
• Molecular Formula: C₉H₁₃NO
• Molecular Weight: 151.21
• Mol File: 1693-66-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 279.2°C at 760 mmHg
• Flash Point: 122.7°C
• Appearance: /
• Density: 1.07g/cm³
• Vapor Pressure: 0.0024mmHg at 25°C
• Refractive Index: 1.562
• CAS DataBase Reference: p-Hydroxy-d-amphetamine(CAS DataBase Reference)
• NIST Chemistry Reference: p-Hydroxy-d-amphetamine(1693-66-9)
• EPA Substance Registry System: p-Hydroxy-d-amphetamine(1693-66-9)

Safety Data

• Hazardous Substances Data: 1693-66-9(Hazardous Substances Data)

Usage

Description

p-Hydroxy-d-amphetamine, also known as Paredrine, is a potent central nervous system stimulant and anorexic agent. It is a metabolite of (S)-Amphetamine (A634245) and is considered the more active isomer of Amphetamine. p-Hydroxy-d-amphetamine induces the release of catecholamines and serotonin by displacing the monoamines from their vesicular storage sites and blocks catecholamine reuptake. Due to its stimulating properties, p-Hydroxy-d-amphetamine is classified as a controlled substance.

Uses

Used in Pharmaceutical Industry:
p-Hydroxy-d-amphetamine is used as a CNS stimulant for its ability to increase alertness, attention, and energy levels. It is particularly useful in the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy, as well as for off-label uses such as weight loss and enhancing cognitive performance.
Used in Research Applications:
In the field of scientific research, p-Hydroxy-d-amphetamine serves as a valuable tool for studying the mechanisms of neurotransmitter release and reuptake, as well as the effects of monoamines on the central nervous system. This helps researchers better understand the role of these neurotransmitters in various physiological and pathological processes.
Used in Controlled Substances Regulation:
As a controlled substance, p-Hydroxy-d-amphetamine is subject to strict regulations and monitoring to prevent its misuse and abuse. This ensures that the compound is used responsibly and only for legitimate medical and research purposes, minimizing the potential for negative health consequences and illegal activities.

InChI:InChI=1/C9H13NO/c1-7(10)6-8-2-4-9(11)5-3-8/h2-5,7,11H,6,10H2,1H3/t7-/m0/s1

Upstream product

• 735231-40-0 C₁₇H₂₁NO 
• 123-11-5 4-methoxy-benzaldehyde 
• 64-13-1 2-amino-1-(4-methyoxyphenyl)propane 
• 17354-63-1 4-(2-nitro-propenyl)-anisole 
• 3938-96-3 ethyl 2-methoxyacetate 
• 103-86-6 p-hydroxyamphetamine 

Relevant articles and documents

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.

Microbial Hydrogenation of Nitroolefins

Micriorganisms which hydrogenate 2-nitro-1-phenyl-1-propene were screend in type cultures and soil samples.Some actinomycetes belonging to Rhodococcus, Nocardia and Mycobacterium asymmetrically reduced the substrate and gave optically active 2-nitro-1-phenylpropane.Among them, Rhodococcus rhodochrous IFO 3338 gave the best results.The satureted compound was obtained quantitatively, when cultivation was carried out for 3 days at 30 oC with a substrate concentration of 0.4percent.The optical purity of the product was seriously affected by the pH of the medium.The more acidic the medium, the higher the enantiomeric excess.The results suggested that non-enzymatic racemization of the product take place even under neutral conditions.Other substrates, such as 2-nitro-1-propene were also converted to optically active 2-nitro-1-substituted propane.