Norpseudoephedrine
Title: Norpseudoephedrine
CAS Registry Number: 492-39-7
CAS Name: (aS)-a-[(1S)-1-Aminoethyl]benzenemethanol
Additional Names: D-threo-2-amino-1-hydroxy-1-phenylpropane; (1S,2S)-2-amino-1-phenylpropan-1-ol; nor-d-y-ephedrine; d-y-norephedrine; d-norisoephedrine; cathine; katine
Molecular Formula: C9H13NO
Molecular Weight: 151.21
Percent Composition: C 71.49%, H 8.67%, N 9.26%, O 10.58%
Literature References: Sympathomimetic amine naturally occurring in the leaves of the khat plant, Catha edulis Forsk. (Celastraceae) and in several species of Ephedra (Ephedraceae) known in traditional medicine as Ma Huang. Isoln from C. edulis: A. Beitter, Arch. Pharm. 239, 17 (1901); O. Wolfes, ibid. 268, 81 (1930); from Ma Huang: S. Smith, J. Chem. Soc. 1928, 51. Physical measurements: C. S. Gibson, B. Levin, ibid. 1929, 2754. Synthesis: W. N. Nagai, S. Kanao, Ann. 470, 157 (1929); J. Sicher, M. Pankova, Collect. Czech. Chem. Commun. 20, 1409 (1955). Pharmacology: H. Hofmann et al., Arzneim.-Forsch. 5, 367 (1955). Clinical pharmacokinetics: F. Frosch, ibid. 27, 665, 1076 (1977). Clinical evaluation for weight reduction: H. Muth, G. Issmeier, Ther. Ggw. 119, 1173 (1980). HPLC determn in urine: P. J. van der Merwe et al., J. Chromatogr. B 661, 357 (1994).
Properties: Prisms from benzene, mp 77.5-78°. [a]20546 +37.9° (c = 3 in methanol). pKa 8.92. Sol in alcohol, chloroform, ether, dil acids.
Melting point: mp 77.5-78°
pKa: pKa 8.92
Optical Rotation: [a]20546 +37.9° (c = 3 in methanol)
 
Derivative Type: Hydrochloride
CAS Registry Number: 2153-98-2
Trademarks: Amorphan (Heumann); Adiposetten (Reiss); Exponcit N (Salutas Fahlberg-List); Fasupond (Eu Rho Pharma); Minusin (Doetsch, Grether)
Molecular Formula: C9H13NO.HCl
Molecular Weight: 187.67
Percent Composition: C 57.60%, H 7.52%, N 7.46%, O 8.53%, Cl 18.89%
Properties: Prisms from alcohol, mp 180-181°. [a]D20 +42.53°. Sol in water.
Melting point: mp 180-181°
Optical Rotation: [a]D20 +42.53°
 
NOTE: This is a controlled substance (stimulant): 21 CFR, 1308.14.
Use: In the optical resolution of externally compensated acids.
Therap-Cat: Anorexic.
Keywords: Anorexic.

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