154-41-6

Usage

Uses

Used in Forensic Applications:
DL-Norephedrine hydrochloride is used as a forensic tool for the detection and analysis of psychoactive substances in various investigations.
Used in Research Applications:
DL-Norephedrine hydrochloride is utilized as a research compound to study the effects of norepinephrine releasing agents on the central nervous system and their potential applications in the development of pharmaceuticals for various conditions.
Used in Pharmaceutical Industry:
DL-Norephedrine hydrochloride is used as an active pharmaceutical ingredient in the development of medications targeting the central nervous system, particularly those related to norepinephrine regulation.
Used in Chemical Research:
DL-Norephedrine hydrochloride is employed as a chemical compound in research studies to understand its properties, interactions, and potential applications in various chemical processes and reactions.

Originator

Propadrine, MSD ,US ,1941

Manufacturing Process

In one route as described in US Patent 2,151,517, 10.7 kg of technical benzaldehyde is vigorously agitated with a solution of 11.0 kg of sodium bisulfite in 50.0 liters of water until the formation of the addition-product is complete. Simultaneously, 8.25 kg of nitroethane is dissolved in a solution of 4.5 kg of caustic soda in 20.0 liters of water and the resultant warm solution is added with vigorous stirring to the magma of benzaldehyde sodium bisulfite. The mixture is agitated for 30 minutes and then allowed to stand overnight.The aqueous portion of the mixture is now siphoned off from the supernatant layer of oily phenylnitropropanol and replaced with a fresh solution of 11.0 kg of sodium bisulfite in 50.0 liters of water. The mixture of phenylnitropropanol and bisulfite solution is now vigorously agitated for 15 minutes in order to remove and recover small amounts of unreacted benzaldehyde, and is then again allowed to stratify. This time, the phenylnitropropanol is siphoned off and filtered to remove a small amount of resinous material. The aqueous solution of sodium bisulfite remaining behind is reacted with benzaldehyde, as described above, thus making the process continuous.The 1-phenyl-2-nitropropanol thus obtained is a colorless oil, specific gravity 1.14 at 20°C, odorless when pure, volatile with steam and boiling at 150° to 165°C under a pressure of 5 mm of mercury. It is soluble in alcohol, ether, acetone, chloroform, carbon tetrachloride, benzene and glacial acetic acid. The yield of 1-phenyl-2-nitropropanolobtained by this procedure is 17.1 to 17.7 kg.It is hydrogenated and converted to the hydrochloride in subsequent steps. The hydrogen chloride has a melting point of 192°-194°C.In an alternative route described in US Patent 3,028,429 propiophenone may be reacted with an alkyl nitrite to give isonitrosopropiophenone which is then hydrogenated and finally converted to the hydrochloride.

Therapeutic Function

Nasal decongestant, Anorexic

Air & Water Reactions

Water soluble.

Reactivity Profile

DL-Norephedrine hydrochloride is incompatible with strong oxidizing agents.

Hazard

Poison by ingestion.

Fire Hazard

Flash point data for DL-Norephedrine hydrochloride are not available; however, DL-Norephedrine hydrochloride is probably combustible.

Safety Profile

Poison by ingestion, subcutaneous, intravenous, intraperitoneal, and intramuscular routes. An experimental teratogen. When heated to decomposition it emits very toxic fumes of HCl and NOx. Used as a raw material in cold and diet tablets.

InChI:InChI=1/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/t7-,9-/m1/s1

Upstream product

• 26251-08-1 2-nitro-1-phenylpropan-1-ol 
• 532-28-5 (RS)-mandelonitrile 
• 910471-77-1 2-(tert-butyldiphenylsilyloxy)-2-phenylacetonitrile 
• 119-51-7 1-phenyl-1,2-propanedione 2-oxime 
• 38222-78-5 threo-1-benzoyloxy-1-phenyl-2-propylammonium chloride 
• 38222-77-4 trans-2,5-diphenyl-4-methyl-1,3-oxazoline 
• 154-41-6 erythro-1-phenyl-1-hydroxy-2-propylammonium chloride 
• 4380-71-6 erythro-2-benzoylamino-1-phenylpropan-1-ol 
• 100-52-7 benzaldehyde 
• 42407-55-6 (1RS,2RS)-2-dibenzylamino-1-phenyl-propan-1-ol; hydrochloride 

Downstream Products

• 1201-56-5 (+/-)-N-methylephedrine 
• 93-55-0 1-phenyl-propan-1-one 
• 60-15-1 2-amino-1-phenylpropane 
• 14593-16-9 N-acetylamphetamine 
• 93860-66-3 O,N-diacetylnorephedrine 

Relevant academic research and scientific papers

Simple preparation process of syn phenylpropanolamines from racemic O-TBDPS cyanohydrins

In this article, a practically interesting route for the diastereoselective synthesis of phenylpropanolamines has been demonstrated for the first time. Using racemic O-tert-butyldiphenylsilyl (TBDPS) cyanohydrins as the starting materials, various syn phenylpropanolamines and derivatives (e.g., norpseudophedrine) have been successfully prepared in exellent diastereoselectivity via a practically interesting process.

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.

NON-CATALYTIC REDUCTION OF Α-OXIMINOKETONES AND Α-OXIMINOALCOHOLS TO ERYTHRO-2-AMINO-1-ARYLALKAN-1-OLS

A non-catalytic reduction of α-oximinoketones 1 and α-oximinoalcohols 2 to erythro-2-amino-1-arylalkan-1-ols 3 with lithium aluminium hydride is reported.The erythro-2-amino-1-arylalkan-1-ols are isolated as their hydrochlorides 5 and characterised as the erythro isomers by benzoylation.

STEREOCHEMICAL COURSE OF THE REACTION OF 2-HALOETHYL ISOTHIOCYANATES WITH NUCLEOPHILES. sTEREOSPECIFIC ROUTE TO 4,5-DISUBSTITUTED Δ2-THIAZOLINES AND THIAZOLIDINE-2-THIONES

Diastereoisomeric 1-chloro-1-phenyl-2-isothiocyanatopropanes have been prepared.They reacted stereospecifically with CH3ONa, diethylamine, aniline and NaSH to give pure cis or trans-4,5-disubstituted Δ2-thiazolines and thiazolidine-2-thiones whose configuration was determined using the nuclear Overhauser effect.The preponderant conformation of diastereoisomeric 1-chloro-1-phenyl-2-isothiocyanatopropanes was estimated on the basis of coupling constants of vicinal protons.