154-41-6 Usage
Description
DL-Norephedrine hydrochloride, also known as Phenylpropanolamine hydrochloride, is a psychoactive amphetamine that acts as a potent norepinephrine releasing agent. It is characterized by its white crystalline powder form, with a bitter taste and solubility in water and alcohol, but insolubility in ether, chloroform, and benzene. DL-Norephedrine hydrochloride is less effective as a dopamine releasing agent and does not affect serotonin release.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 154-41-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,5 and 4 respectively; the second part has 2 digits, 4 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 154-41:
(5*1)+(4*5)+(3*4)+(2*4)+(1*1)=46
46 % 10 = 6
So 154-41-6 is a valid CAS Registry Number.
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
154-41-6Relevant articles and documents
Simple preparation process of syn phenylpropanolamines from racemic O-TBDPS cyanohydrins
Li, Qing-Lan,Tang, Shi,Zhou, Dong,Tang, Xin-Mei
supporting information, p. 1600 - 1607 (2014/06/09)
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.
NON-CATALYTIC REDUCTION OF Α-OXIMINOKETONES AND Α-OXIMINOALCOHOLS TO ERYTHRO-2-AMINO-1-ARYLALKAN-1-OLS
Oppong-Boachie, Francis Kwabena
, p. 293 - 298 (2007/10/02)
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.
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