DL-Norephedrine

Common Name dl-norephedrine hydrochloride 2-amino-1-phenyl-1-propanol hydrochloride... 

Common Name dl-Norephedrine hydrochloride 2-Amino-l-phenyl-l-propanol hydrochloride... 

SYNS a-(l-AMINOETHYL)BENZENEMETHANOL HYDROCHLORIDE a-(l-AMINOETHYL)BENZYL ALCOHOL HYDROCHLORIDE ( )-2-AMINO-l-PHENYL-l-PROPANOL HYDROCHLORIDE O-HYDROXY-P-AMINOPROPYLBENZENE HYDROCHLORIDE MONHYDRIN MUCORAMA MYDRIATINE dl-NOREPHEDRINE HYDROCHLORIDE dl-l-PHENYL-2-AMINO-l-PROPANOL MONOHYDROCHLORIDE PHENYLPROPANOLAMINE HYDROCHLORIDE... 

DL-( )-Norephedrine hydrochloride [Propadrin, ( )- ijtAro-lJ. , 2 / -2-amino-l-phenyl-l-propanol hydrochloride] [154-41-6] m 194-196° (also 194° was reported), pK 8.20. It crystallises in plates from absolute EtOH or isoPrOH, and the )-oxalate has m 245°(dec) (plates from H2O). The 2,4-dinitrobenzoate has m 86-88° (from EtOH) and the 3,5-dinitrobenzoate has m 78-79° (from EtOH). It is a mixed anti-sympathomimetic and used as a nasal anticongestant. [cf Atkins Cramer J Am Chem Soc 52 4349 1930, Krantz Hartimg JA/w Pharm Assoc 19 461 1930, Fischer Plein JA/w Pharm Assoc 44 313 1955, Beilstein 13 I 252,13II371,13 III 1717,13 IV 1875.]... 

A soln. of benzoylglycolyl chloride in chloroform added during 1 hr. to a stirred soln. of dl-norephedrine and triethylamine in the same solvent, and refluxed 1 hr. dl-cri/f/iro-2-henzoylglycolylamino-l-hydroxy-l-phenylpropane (Y 94%) stirred and refluxed 16 hrs. with LiAlH4 in ether, and the product isolated as the hydrochloride dl-N-(2-hydroxyethyl)norephedrine hydro-... 

Hoover and Hass hydrogenated 2-nitro-l-phenyl-l-propanol over Raney Ni in ethanol in the presence of sufficient carbon dioxide to produce a pressure of 2.1 MPa and obtained the corresponding amino alcohol (a mixture of /-norephedrine and dl-norisoephedrine) in 87% yield.18 The formation of /V-ethylbenzylamine, a byproduct, was depressed to 5% under these conditions (eq. 9.6). Without carbon dioxide the yield of /V-clhylbcnzylaminc was approximately 45%. 

According to Chen, Wu, and Henriksen, norephedrines have a strong action, comparable to that of the ephedrines nor-d- -ephedrine has a weaker action than I or dl-ephedrine, but stronger than d- f -ephedrine. 

DL-2-(4-Hydroxyphenyl)-2-propylamine (4-hydroxyamphetamine) (C H ON) 2-(3,4,6-Trihydroxyphenyl)ethylamine (6-hydroxydopamine) (Cg H11O3N) DL-2-Amino-l-(4-hydroxyphenyl)ethanol (octopamine) DL-2-Amino-l-phenylpropanol (norephedrine) (C H gON)... 

A soln. of 0.5 g. dl-N-(2-hydroxyethyl) norephedrine hydrochloride (prepn. s. 500) in coned, sulfuric acid left 17 hrs. at room temp., and the product isolated as the hydrochloride 0.4 g. dl-frans-3-methyl-2-phenylmorpholine hydrochloride. F. H. Clarke, J, Org. Chem. 27, 3251 (1962). 

Kaddoumi, A. Nakashima, M.N. Nakashima, K. Fluorometric determination of DL-fenfluramine, DL-norfenfluramine and phentermine in plasma by achiral and chiral high-performance liquid chromatography, J.Chromatogr.B, 2001, 763, 79-90. [fluorescence detection derivatization human rat LOD 10 nM ephedrine norephedrine]... 

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