6714. Norpseudoephedrine

Nomenclature

CAS number: 492-39-7
(αS)-α-[(1S)-1-Aminoethyl]benzenemethanol; d-threo-2-amino-1-hydroxy-1-phenylpropane; (1S,2S)-2-amino-1-phenylpropan-1-ol; nor-d-ψ-ephedrine; d-ψ-norephedrine; d-norisoephedrine; cathine; katine.
C9H13NO; mol wt 151.21.
C 71.49%, H 8.67%, N 9.26%, O 10.58%.

Description and 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).

Chemical structure

Properties

Prisms from benzene, mp 77.5-78°. [α]20546 +37.9° (c = 3 in methanol). pKa 8.92. Sol in alcohol, chloroform, ether, dil acids.

Derivative

Hydrochloride.

Nomenclature

CAS number: 2153-98-2
Amorphan (Heumann); Adiposetten (Reiss); Exponcit N (Salutas Fahlberg-List); Fasupond (Eu Rho Pharma); Minusin (Doetsch, Grether).
C9H13NO.HCl; mol wt 187.67.
C 57.60%, H 7.52%, N 7.46%, O 8.53%, Cl 18.89%.

Properties

Prisms from alcohol, mp 180-181°. [α]D20 +42.53°. Sol in water.

Note

This is a controlled substance (stimulant): 21 CFR, 1308.14.

Use

In the optical resolution of externally compensated acids.

Therapeutic Category

Anorexic.

Keywords

Anorexic