Phenylpropanolamine
Structural Formula Vector Image
Title: Phenylpropanolamine
CAS Registry Number: 14838-15-4
CAS Name: (aS)-rel-a-[(1R)-1-Aminoethyl]benzenemethanol
Additional Names: (1RS,2SR)-2-amino-1-phenyl-1-propanol; erythro-2-amino-1-phenyl-1-propanol; dl-norephedrine
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; racemic mixture of d- and l-norephedrine. Prepn: F. W. Calliess, Arch. Pharm. 250, 141 (1912); P. Rabe, Ber. 45, 2163 (1912); F. W. Hoover, H. B. Hass, J. Org. Chem. 12, 506 (1947); and prepn of enantiomers: W. N. Nagai, S. Kanao, Ann. 470, 157 (1929); C. Jarowski, W. H. Hartung, J. Org. Chem. 8, 564 (1943). Crystal structure: A. Podder et al., Indian J. Phys. 53A, 652 (1979). HPLC determn in plasma and urine: K. Yamashita et al., J. Chromatogr. 527, 103 (1990). Clinical studies of decongestant activity: O. K. Haugeto et al., J. Otolaryngol. 10, 359 (1981); M. Bende et al., Rhinology 23, 43 (1985); in stress incontinence: E. Fossberg et al., Urol. Int. 38, 293 (1983); in weight loss: D. E. Schteingart, Int. J. Obes. 16, 487 (1992). Toxicity: E. I. Goldenthal, Toxicol. Appl. Pharmacol. 18, 185 (1971). Comprehensive description: I. Kanfer et al., Anal. Profiles Drug Subs. 12, 357-383 (1983). Review of anorexic effects: P. J. Wellman, Neurosci. Biobehav. Rev. 14, 339-355 (1990); of toxicology: R. Hanzlick, G. Davis, Am. J. Forensic Med. Pathol. 13, 37-41 (1992). Evaluation of risk of hemorrhagic stroke: W. N. Kernan et al., N. Engl. J. Med. 343, 1826 (2000).
Properties: mp 101-101.5°.
Melting point: mp 101-101.5°
 
Derivative Type: Hydrochloride
CAS Registry Number: 154-41-6
Trademarks: Boxogetten (Cheplapharm); Kontexin (Pfizer); Monydrin (AstraZeneca); Proin (PRN); Propalin (V oquinol); UriCon (ProLabs)
Properties: Crystals, mp 190-194°. Odor resembling that of crude benzoic acid. pKa 9.44±0.04. Freely sol in water, alcohol. Practically insol in ether, chloroform, benzene. The aq soln is neutral to litmus. LD50 orally in rats: 1490 mg/kg (Goldenthal).
Melting point: mp 190-194°
pKa: pKa 9.44±0.04
Toxicity data: LD50 orally in rats: 1490 mg/kg (Goldenthal)
 
Derivative Type: (+)-Form hydrochloride
Properties: [a]D25 +32° (water). mp 171-172°.
Melting point: mp 171-172°
Optical Rotation: [a]D25 +32° (water)
 
Derivative Type: D-threo-Form see Norpseudoephedrine
 
Therap-Cat: Decongestant (nasal); anorexic; in treatment of urinary incontinence.
Therap-Cat-Vet: In treatment of urinary incontinence in dogs and cats; decongestant (nasal).
Keywords: a-Adrenergic Agonist; Anorexic; Decongestant.

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