2706-50-5

Usage

Uses

Used in Pharmaceutical Industry:
rac AMphetamine Hydrochloride is used as a CNS stimulant for the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy. Its stimulant effects help increase focus, attention, and reduce impulsiveness in individuals with ADHD. Additionally, it is used to promote wakefulness in patients suffering from narcolepsy, a condition characterized by excessive daytime sleepiness.
Used in Weight Loss Applications:
In the weight loss industry, rac AMphetamine Hydrochloride is used as an anorexic agent to suppress appetite and promote weight loss. Its ability to decrease hunger and increase metabolism makes it a potential treatment option for obesity and related health conditions.
Used in Research and Development:
rac AMphetamine Hydrochloride is also utilized in the research and development of new medications and therapies. Its psychoactive properties and effects on the CNS make it a valuable compound for studying the mechanisms of addiction, mental health disorders, and the development of novel treatments for various conditions.

Safety Profile

Poison by subcutaneous,intravenous, and intraperitoneal routes. When heated to decomposition it emits very toxic fumes of HCl and NOx.See other amphetamine entries.

Upstream product

• 345308-53-4 C₂₁H₂₂NOP 
• 31731-87-0 1-methyl-2-phenylethylmagnesium bromide 
• 39861-30-8 2-chloro-1-methyl-2-phenyl-ethylamine; hydrochloride 
• 3198-15-0 (1R,2S)-(-)-norephedrine hydrochloride 
• 51-64-9 dexamfetamine 
• 698-87-3 3-phenyl-2-propanol 
• 61380-47-0 (±)-1-phenylpropanyl-2-yl methansulfonate 
• 103-65-1 phenylpropane 
• 1009-67-2 2-methyl-3-phenylpropanoic acid 
• 13213-36-0 1-phenylpropan-2-one oxime 
• 82572-07-4 C₂₁H₂₀NOP 
• 300-57-2 allylbenzene 
• 7761-64-0 diethyl (1-phenylpropan-2-yl)phosphoramidate 

Downstream Products

• 17590-01-1 amphetaminil 
• 103994-79-2 3-[(1-Methyl-2-phenyl-ethylamino)-methyl]-5-pyridin-4-yl-3H-[1,3,4]oxadiazole-2-thione; hydrochloride 
• 33061-37-9 N-(1-Methyl-2-phenylethyl)harnstoff 
• 6338-74-5 4-methyl-N-(1-phenylpropan-2-yl)benzenesulfonamide 
• 22293-47-6 3-(α-methylphenethyl)sydnone imine 

Relevant academic research and scientific papers

Synthesis of α-Substituted Primary Benzylamines through Copper-Catalyzed Cross-Dehydrogenative Coupling

A copper-catalyzed route to α-substituted, primary benzylamines by C-H functionalization of alkylarenes is described. The method directly affords the amine hydrochloride salt. Catalyst loadings down to 0.1 mol % in combination with scalability, insensitivity to air and moisture, and no need for column chromatography makes the procedure highly practical. The facile synthesis of the racemate of a blockbuster drug highlights the relevance for the development of pharmaceuticals. Preliminary mechanistic data are also included.

Catalytic Staudinger Reduction at Room Temperature

We report an efficient catalytic Staudinger reduction at room temperature that enables the preparation of a structurally diverse set of amines from azides in excellent yields. The reaction is based on the use of catalytic amounts of triphenylphosphine as a phosphine source and diphenyldisiloxane as a reducing agent. Our catalytic Staudinger reduction exhibits a high chemoselectivity, as exemplified by reduction of azides over other common functionalities, including nitriles, alkenes, alkynes, esters, and ketones.

Cross-Coupling of Alkyl Redox-Active Esters with Benzophenone Imines: Tandem Photoredox and Copper Catalysis

Alkyl amines are an important class of organic compounds in medicinal and materials chemistry. Until now very have been very few methods for the synthesis of alkyl amines by metal-catalyzed cross-coupling of alkyl electrophiles with nitrogen nucleophiles. Described here is an approach to employ tandem photoredox and copper catalysis to enable the cross-coupling of alkyl N-hydroxyphthalimide esters, readily derived from alkyl carboxylic acids, with benzophenone-derived imines. Hydrolysis of the coupling products furnish alkylated primary amines. Primary, secondary, and tertiary alkyl groups can be transferred, and the coupling tolerates a diverse set of functional groups. The method allows rapid functionalization of natural products and drugs, and can be used to expedite syntheses of pharmaceuticals from readily available chemical feedstocks.

Sustainable organophosphorus-catalysed Staudinger reduction

A highly efficient and sustainable catalytic Staudinger reduction for the conversion of organic azides to amines in excellent yields has been developed. The reaction displays excellent functional group tolerance to functionalities that are otherwise prone to reduction, such as sulfones, esters, amides, ketones, nitriles, alkenes, and benzyl ethers. The green nature of the reaction is exemplified by the use of PMHS, CPME, and a lack of column chromatography.

Stereoretentive Deuteration of α-Chiral Amines with D2O

We present the direct and stereoretentive deuteration of primary amines using Ru-bMepi (bMepi = 1,3-(6′-methyl-2′-pyridylimino)isoindolate) complexes and D2O. High deuterium incorporation occurs at the α-carbon (70-99%). For α-chiral amines, complete retention of stereochemistry is achieved when using an electron-deficient Ru catalyst. The retention of enantiomeric purity is attributed to a high binding affinity of an imine intermediate with ruthenium, as well as to a fast H/D exchange relative to ligand dissociation.

From the production of amphetamine phenylpropanolamine

A process for making compound of formula Ifrom a phenylpropanolamine salt of formula IIwherein:R1 is hydrogen or a lower alkyl group;each R2 is independently a hydrogen, halogen, lower alkyl group, lower alkoxy groups, lower alkyl group substituted with 1 to 5 halogens, lower alkoxy groups substituted with 1 to 5 halogens, or both R2 together when on adjacent carbons constitute a -O(CH2)xO- where x is 1 to 4, thereby forming a ring structure fused with the phenyl group;R3 is a C1-C8-alkyl group, a C1-C12-aralkyl group, C1-C12-alkaryl group, or a phenyl group, each optionally substituted by 1 to 5 substituents selected from halogen, hydroxy, or C1-C6-alkyl; andHX is an equivalent of an organic or inorganic acid,the process comprising:(a) acylating the phenylpropanolamine salt of formula II with an acylating agent in a solvent at elevated temperature to make a reaction mixture containing an O-acylated phenylpropanolamine salt of formula III which can be isolated by the addition of a crystallization solvent, or optionally this mixture can be used in the next step; and(b) hydrogenating the O-acylated phenylpropanolamine salt to make the compound of formula I in the presence of a catalyst.

Synthesis of primary amines by the electrophilic amination of Grignard reagents with 1,3-dioxolan-2-one O-sulfonyloxime

(Chemical equation presented) Primary amines are prepared by the electrophilic amination of Grignard reagents with 4,4,5,5-tetramethyl-1,3- dioxolan-2-one O-phenylsulfonyloxime and the acidic hydrolysis of the resulting imines.

Synthesis of primary sec-alkylamines via nucleophilic ring-opening of N-phosphorylated aziridines

The novel ring-opening reaction of various 2-alkyl- and 2,2-dimethyl-N-(diethoxyphosphoryl)aziridines (1) and (10) with copper-modified Grignard reagents proceeds regiospecifically at the less hindered carbon. The diethyl N-sec-alkylphosphoramidates (2) thus obtained may efficiently be converted to primary sec-alkylamine hydrochlorides (3) by refluxing with 20% hydrochloric acid. 2,3-Disubstituted N-phosphorylated aziridines except N-phosphorylated cyclohexenimine (4) do not react under the described conditions. Copper-mediated reaction of 2-phenyl-N-(diethoxyphosphoryl)aziridine (7) with Grignard reagents affords a mixture of regioisomers (8) and (9) but still with the preference of ring-opening at the carbon of lesser substitution.