ChemicalBook > Product Catalog > Analytical Chemistry > Standard > Pharmaceutical Impurity Reference Standards > Phenylephrine
Phenylephrine Chemical Properties
- Melting point:171°C
- Boiling point:295.79°C (rough estimate)
- Density 1.1222 (rough estimate)
- refractive index -55.5 ° (C=5, 1mol/L HCl)
- solubility Slightly soluble in water, sparingly soluble in methanol, slightly soluble in ethanol (96 per cent). It dissolves in dilute mineral acids and in dilute solutions of alkali hydroxides.
- form neat
- pkapKa 8.9 (Uncertain)
- CAS DataBase Reference59-42-7(CAS DataBase Reference)
- NIST Chemistry ReferenceBenzenemethanol, 3-hydroxy-«alpha»-[(methylamino)methyl]-, (r)-(59-42-7)
Phenylephrine Usage And Synthesis
- Chemical PropertiesWhite or almost white, crystalline powder.
- UsesL-Phenylephrine is an adrenergic α1A receptor agonist (Ki = 1.4 μM) that demonstrates selectivity against the α1B and α1C receptor subtypes (Kis = 23.9 and 47.8 μM, respectively). By stimulating adrenergic α1 receptors, L-phenylephrine can induce aortic smooth muscle contractions, although reported relative affinity and potency values in rabbit are 5-fold weaker compared to that of L-norepinephrine. This compound is frequently used to precontract smooth muscle in preparations designed to study the properties of various vasodilator agents. Because L-phenylephrine acts on adrenergic α1 receptors in the arterioles of the nasal mucosa to produce constriction, it has been examined clinically as an oral decongestant.
- DefinitionChEBI: A member of the class of the class of phenylethanolamines that is (1R)-2-(methylamino)-1-phenylethan-1-ol carrying an additional hydroxy substituent at position 3 on the phenyl ring.
- brand nameAfrin 4 Hour Nasal Spray (Schering-Plough Health Care); Biomydrin (Parke-Davis); Mydfrin (Alcon); Neo-Synephrine (Sterling Health U.S.A.); Nostril (Boehringer Ingelheim);Fenox;Forte;Isopto;Minims;Visadron.
- General Description(Neo-Synephrine, a prototypical selectivedirect-acting 1-agonist) differs from E only inlacking a p-OH group. It is orally active, and its DOA isabout twice that of E because it lacks the catechol moietyand thus is not metabolized by COMT. However, its oralbioavailability is less than 10% because of its hydrophilicproperties (log P＝0.3), intestinal 3 -O-glucuronidation/sulfation and metabolism by MAO. Lacking the p-OHgroup, it is less potent than E and NE but it is a selectiveα1-agonist and thus a potent vasoconstrictor. It is usedsimilarly to metaraminol and methoxamine for hypotension.Another use is in the treatment of severe hypotensionresulting from either shock or drug administration. It alsohas widespread use as a nonprescription nasal decongestantin both oral and topical preparations. When applied tomucous membranes, it reduces congestion and swelling byconstricting the blood vessels of the membranes. In theeye, it is used to dilate the pupil and to treat open-angleglaucoma. In addition, it is used in spinal anesthesia toprolong the anesthesia and to prevent a drop in blood pressureduring the procedure. It is relatively nontoxic and produceslittle CNS stimulation. Metaraminol is just anotherexample.
- Safety ProfilePoison by ingestion, subcutaneous, intravenous, intraperitoneal, and intraduodenal routes. Human systemic effects by ocular route: blood pressure increase. An experimental teratogen. Other experimental reproductive effects. A nasal decongestant. When heated to decomposition it emits toxic fumes of NOx.
- Veterinary Drugs and TreatmentsPhenylephrine has been used to treat hypotension and shock (after
adequate volume replacement), but many clinicians prefer to use
an agent that also has cardiostimulatory properties. Phenylephrine
is recommended for use to treat hypotension secondary to drug
overdoses or idiosyncratic hypotensive reactions to drugs such as
phenothiazines, adrenergic blocking agents, and ganglionic blockers.
Its use to treat hypotension resulting from barbiturate or other
CNS depressant agents is controversial. Phenylephrine has been
used to increase blood pressure to terminate attacks of paroxysmal
supraventricular tachycardia, particularly when the patient is also
hypotensive. Phenylephrine has been used to both treat hypotension
and prolong the effects of spinal anesthesia.
Ophthalmic uses of phenylephrine include use for some diagnostic eye examinations, reducing posterior synechiae formation, and relieving pain associated with complicated uveitis. It has been applied intranasally in an attempt to reduce nasal congestion.
- Phenylephrine Phenethyl alcohol N,N-Dimethyl-1,4-phenylenediamine Doxifluridine Ursodeoxycholic acid Methyl Methyl acrylate Methyl bromide Benzyl alcohol D-METHAMPHETAMINE 2-Aminobenzylchloride DL-PHENYLEPHRINE HYDROCHLORIDE Chenodeoxycholic acid CHLOROPHOSPHONAZO III (-)-2-[METHYLAMINO]-1-PHENYLPROPANE Methylparaben Tris Base Phenylephrine hydrochloride
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