7916. Pseudoephedrine

Nomenclature

CAS number: 90-82-4
(αS)-α-[(1S)-1-(Methylamino)ethyl]benzenemethanol; (1S,2S)-2-methylamino-1-phenylpropan-1-ol; d-ψ-ephedrine; d-isoephedrine.
C10H15NO; mol wt 165.23.
C 72.69%, H 9.15%, N 8.48%, O 9.68%.

Description and references

Sympathomimetic amine found in plants of the genus Ephedra (Ephedraceae) known in traditional medicine as Ma Huang. α-Adrenergic agonist; (+)-threo-isomer of ephedrine, q.v. Isoln from E. vulgaris: A. Ladenburg, C. Oelschl"agel, Ber. 22, 1823 (1889). Synthesis: E. Sp"ath, R. G"ohring, Monatsh. Chem. 41, 319 (1920). HPLC determn in Ma Huang: B. J. Gurley et al., J. Pharm. Sci. 87, 1547 (1998); in plasma: P. Guo et al., Biomed. Chromatogr. 13, 61 (1999). Toxicity: M. D. Fairchild, G. A. Alles, J. Pharmacol. Exp. Ther. 158, 135 (1967). Comprehensive description: S. A. Benezra, J. W. McRae, Anal. Profiles Drug Subs. 8, 489-507 (1979). Review of clinical pharmacology: D. T. D. Hughes et al., J. Clin. Hosp. Pharm. 8, 315-321 (1983). Clinical trial for prevention of otic barotrauma: J. S. Jones et al., Am. J. Emerg. Med. 16, 262 (1998); in nasal congestion: D. Taverner et al., Clin. Otolaryngol. 24, 47 (1999).

Chemical structure

Properties

Crystals from ether, mp 118-118.7°. [α]D20 +51.2° (in ethanol). Sparingly sol in water. Freely sol in alc or ether.

Derivative

Hydrochloride.

Nomenclature

CAS number: 345-78-8
Efidac 24 (Innomed); Galpseud (Thorton & Ross); Galsud (Thorton & Ross); Rhinalair (Fabre); Otrinol (Novartis); Sudafed (Pfizer).
C10H15NO.HCl; mol wt 201.69.
C 59.55%, H 8.00%, N 6.94%, O 7.93%, Cl 17.58%.

Properties

Needles, mp 182.5-183.5°. [α]D20 +62.05°. uv max (ethanol): 208, 251, 257, 264 nm (ε 8300, 161, 201, 161). pKa 9.22. Soly at 25° (g/ml): water 2.0; chloroform 0.011; ethanol 0.278. Practically insol in ether. Partition coefficient (25°): 0.010 (n-octanol/water, pH 1.2); 0.049 (n-octanol/water, pH 6.0). LD50 i.p. in mice: 1.0 mmole/kg (Fairchild, Alles).

Derivative

Sulfate.

Nomenclature

CAS number: 7460-12-0
C20H30N2O2.H2SO4; mol wt 428.54.
C 56.05%, H 7.53%, N 6.54%, O 22.40%, S 7.48%.

Properties

White crystalline powder, bitter taste. mp 174-179°. [α]D20 + 56.0-58.0°. Very freely sol in water; freely sol in ethanol. Practically insol in ether.

Therapeutic Category

Decongestant (nasal).

Therapeutic Category (Veterinary)

In treatment of urinary incontinence; decongestant.

Keywords

Decongestant; α-Adrenergic Agonist