7286. Phenylephrine

Nomenclature

CAS number: 59-42-7
(αR)-3-Hydroxy-α-[(methylamino)methyl]benzenemethanol; (-)-m-hydroxy-α-[(methylamino)methyl]benzyl alcohol; l-1-(m-hydroxyphenyl)-2-methylaminoethanol; l-α-hydroxy-β-methylamino-3-hydroxy-1-ethylbenzene; m-methylaminoethanolphenol; metaoxedrin.
C9H13NO2; mol wt 167.21.
C 64.65%, H 7.84%, N 8.38%, O 19.14%.

Description and references

α-Adrenergic agonist. Prepn: H. Legerlotz, US 1932347 (1933 to Frederick Stearns); E. D. Bergmann, M. Sulzbacher, J. Org. Chem. 16, 84 (1951); M. K. Gurjar et al., Org. Process Res. Dev. 2, 422 (1998). Spectrophotometric determn: S. A. Shama, J. Pharm. Biomed. Anal. 30, 1385 (2002). Toxicity data: M. R. Warren, H. W. Werner, J. Pharmacol. Exp. Ther. 86, 284 (1946). Clinical efficacy in mydriasis: V. Tanner, A. G. Casswell, Eye 10, 95 (1996). Clinical evaluation in fecal incontinence: M. J. Cheetham et al., Gut 48, 356 (2001). Comprehensive description: C. A. Gaglia, Jr., Anal. Profiles Drug Subs. 3, 483-512 (1974). Review of ophthalmologic uses: S. M. Meyer, F. T. Fraunfelder, Ophthalmology 87, 1177-1180 (1980); of clinical trials vs ephedrine, q.v., in treatment of hypotension during cesarean delivery: A. Lee et al., Anesth. Analg. 94, 920-926 (2002).

Chemical structure

Properties

mp 170-171°.

Derivative

Hydrochloride.

Nomenclature

CAS number: 61-76-7
Ak-Dilate (Akorn); Ak-Nefrin (Akorn); Alconefrin (Polymedica); Incostop (SLA Pharma); Mydfrin (Alcon); Neo-Synephrine (Bayer); Nostril (Novartis); Prefrin (Allergan); Rhinall (Scherer).
C9H13NO2.HCl; mol wt 203.67.
C 53.07%, H 6.93%, N 6.88%, O 15.71%, Cl 17.41%.

Properties

Bitter crystals, mp 140-145°. [α]D -44.0° (c = 2.16 in H2O). pK1 8.77; pK2 9.84. uv max (0.05 N HCl): 216, 274, 279 nm (ε × 10-3 5.91, 1.81, 1.65). uv max (0.05 N NaOH): 239, 292.5 (ε × 10-3 8.95, 3.04). Freely sol in water or alcohol. LD50 in rats (mg/kg): 17 ±1.1 i.p.; 33 ±2.0 s.c. (Warren, Werner).

Therapeutic Category

Mydriatic; decongestant; in treatment of fecal incontinence.

Keywords

α-Adrenergic Agonist; Decongestant; Mydriatic