N-Methylephedrine
Title: N-Methylephedrine
CAS Registry Number: 552-79-4
CAS Name: a-[1-(Dimethylamino)ethyl]benzenemethanol
Additional Names: erythro-a-[1-(dimethylamino)ethyl]benzyl alcohol; 2-dimethylamino-1-phenylpropanol; N,N-dimethylnorephedrine
Molecular Formula: C11H17NO
Molecular Weight: 179.26
Percent Composition: C 73.70%, H 9.56%, N 7.81%, O 8.93%
Literature References: Isoln of l-form from Ephedra distachya L. (E. vulgaris Rich.), and allied Gnetaceae: Smith, J. Chem. Soc. 1927, 2056; Wolfes, Arch. Pharm. 268, 327 (1930). Prepn of l-form: Smith, loc. cit.; of d-, l-, and dl-forms, and resolution of racemic mixture: Nagai, Kanao, Ann. 470, 157 (1929); of dl-form: Pfanz, Müller, Arch. Pharm. 288, 11 (1955).
 
Derivative Type: dl-Form
Properties: Crystals from petr ether or methanol, mp 63.5-64.5°. Readily sol in the usual solvents.
Melting point: mp 63.5-64.5°
 
Derivative Type: dl-Form hydrochloride
Trademarks: Metheph (Napp)
Properties: Crystals from acetone, mp 207-208°.
Melting point: mp 207-208°
 
Derivative Type: d-Form
Properties: Crystals, mp 87-87.5°. [a]D20 +29.2° (c = 4 in methanol).
Melting point: mp 87-87.5°
Optical Rotation: [a]D20 +29.2° (c = 4 in methanol)
 
Derivative Type: d-Form hydrochloride
Properties: Crystals from ethyl acetate, mp 192°. [a]D20 +30.1°.
Melting point: mp 192°
Optical Rotation: [a]D20 +30.1°
 
Derivative Type: l-Form
Properties: Crystals from petr ether, mp 87-88°. [a]D -29.5° (c = 4.5 in methanol).
Melting point: mp 87-88°
Optical Rotation: [a]D -29.5° (c = 4.5 in methanol)
 
Derivative Type: l-Form hydrochloride
Properties: Crystals from ethyl acetate or alcohol, mp 192°. [a]D20 -29.8° (c = 4.6). Readily sol in water; less sol in alcohol; sparingly sol in acetone.
Melting point: mp 192°
Optical Rotation: [a]D20 -29.8° (c = 4.6)
 
Derivative Type: b-Camphorsulfonate
Additional Names: N-Methylephedrine camsylate
Trademarks: Tybraine (Nicholas)
 
Therap-Cat: Analeptic.
Keywords: Bronchodilator; Ephedrine Derivatives.

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