(R)-Phenylephrine Hydrochlorid Chemical Properties

Melting point:

143-145 °C(lit.)

alpha 

-47 º (c=2, H2O)

refractive index 

-45.5 ° (C=1, H2O)

Flash point:

9℃

storage temp. 

2-8°C

solubility 

Freely soluble in water and in ethanol (96 per cent).

form 

Crystalline Powder

pka

pK1 8.77; pK2 9.84(at 25℃)

color 

White to almost white

PH

pH (10g/L, 25℃) : 4.5～5.5

Water Solubility 

>=10 g/100 mL at 21 ºC

Merck 

14,7286

BRN 

4158948

Stability:

Hygroscopic

LogP

-0.310

CAS DataBase Reference

61-76-7(CAS DataBase Reference)

EPA Substance Registry System

Phenylephrine hydrochloride (61-76-7)

Safety Information

Hazard Codes 

Xn,T,F

Risk Statements 

22-36/37/38-39/23/24/25-23/24/25-11

Safety Statements 

26-36-37/39-45-36/37-16-7

RIDADR 

3249

WGK Germany 

3

RTECS 

DO7525000

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

29225090

Toxicity

LD50 in rats (mg/kg): 17 ±1.1 i.p.; 33 ±2.0 s.c. (Warren, Werner)

MSDS

• Language:English Provider:(R)-(-)-1-(3-Hydroxyphenyl)-2-methylaminoethanol hydrochloride
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

(R)-Phenylephrine Hydrochlorid Usage And Synthesis

Description

R-(-)-Phenylephrine is an adrenergic α_1A receptor agonist (K_i = 1.4 μM) that demonstrates selectivity against the α_1B and α_1C receptor subtypes (K_is = 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.

Chemical Properties

Phenylephrine Hydrochloride is white or nearly white crystalline substance, odorless, bitter taste. Solutions are acid to litmus paper, freely soluble in water and in alcohol. Levorotatory in solution.

Chemical Properties

white to almost white crystalline powder

Originator

Neosynephrine, Badrial, France ,1953

Uses

(R)-Phenylephrine Hydrochloride is an α-Adrenergic agonist. Mydriatic; decongestant.

Uses

Phenylephrine hydrochloride is used medically as a vasoconstrictor and pressor drug. It is chemically related to epinephrine and ephedrine. Actions are usually longer lasting than the latter two drugs. The action of phenylephrine hydrochloride contrasts sharply with epinephrine and ephedrine, in that its action on the heart is to slow the rate and to increase the stroke output, inducing no disturbance in the rhythm of the pulse. In therapeutic doses, it produces little if any stimulation of either the spinal cord or cerebrum. The drug is intended for the maintenance of an adequate level of blood pressure during spinal and inhalation anesthesia and for the treatment of vascular failure in shock, shock-like states, and drug-induced hypotension, or hypersensitivity. It is also used to overcome paroxysmal supraventricular tachycardia, to prolong spinal anesthesia, and as a vasoconstrictor in regional analgesia. Caution is required in the administration of phenylephrine hydrochloride to elderly persons, or to patients with hyperthyroidism, bradycardia, partial heart block, myocardial disease, or severe arteriosclerosis. The brand name Neo-Synephrine? is also used to designate another product (nose drops) which does not contain phenylephrine hydrochloride. The nose drops contain xylometazoline hydrochloride.

Uses

DECONGESTANTS

Definition

ChEBI: A hydrochloride that is the monohydrochloride salt of phenylephrine.

Manufacturing Process

4.5 g of the hydrochloride of m-hydroxymethylaminoacetophenone aredissolved in a small amount of water; to the solution a solution of colloidal palladium obtained from palladiumchloride is added, and the mixture is treated with hydrogen.
After diluting the reaction liquid with acetone it is filtered, and the residue obtained after the evaporation of the filtrate in vacuo, and complete drying over pentoxide of phosphorus is then dissolved in absolute alcohol, and to this is added about the same volume of dry ether, until turbidity just commences to occur. After a short time the hydrochloride of the m-hydroxyphenylethanolmethylamine will separate out as a colorless mass of crystals at a melting point of 142°C to 143°C.

brand name

Afrin 4 Hour Nasal Spray (Schering-Plough Health Care); Biomydrin (Parke-Davis); Mydfrin (Alcon); Neo-Synephrine (Sterling Health U.S.A.); Nostril (Boehringer Ingelheim).

Therapeutic Function

Adrenergic

General Description

Odorless white microcrystalline powder. Bitter taste. pH (1% aqueous solution) about 5.

Air & Water Reactions

May be sensitive to prolonged exposure to air and light. Water soluble.

Reactivity Profile

Phenylephrine hydrochloride is incompatible with acids, acid chlorides, acid anhydrides and oxidizing agents. Phenylephrine hydrochloride is also incompatible with butacaine, alkalis and ferric salts.

Fire Hazard

Flash point data for Phenylephrine hydrochloride are not available; however, Phenylephrine hydrochloride is probably combustible.

Biological Activity

α 1 -adrenoceptor agonist; pK i values are 5.86, 4.87 and 4.70 for α 1D , α 1B and α 1A receptors respectively.

Contact allergens

Phenylephrine hydrochloride is an alpha-adrenergic agonist, used as a mydriatic and decongestant in eyedrops.

Safety Profile

Poison by ingestion, intraperitoneal, subcutaneous, intravenous,and intramuscular routes. Mutation data reported. When heated to decomposition it emits very toxic fumes of HCl and NOx.

Veterinary Drugs and Treatments

Phenylephrine is a vasoconstrictor used to differentiate conjunctival vascular injection (blanches with phenylephrine application) versus deep episcleral injection (blanches incompletely) associated with uveitis, glaucoma, or scleritis. It is also used prior to conjunctival surgery to reduce hemorrhage and in combination with atropine prior to cataract or other intraocular surgeries that require maximal pupillary dilation. Phenylephrine can be used to confirm the diagnosis of Horner’s syndrome. Dilution of 2.5% phenylephrine solution with saline (1:10) produces a 0.25% solution. Normal eyes will not demonstrate mydriasis in response to this low concentration of phenylephrine. Third order Horner’s syndrome of greater than two weeks duration is associated with receptor up regulation and therefore a response to 0.25% phenylephrine is noted. In this way, the diagnosis of Horner’s is confirmed and a suggestion as to whether or not the condition is 2nd or 3rd order in nature.
In dogs, maximum mydriasis persists for about 2 hours and effects may last for up to 18 hours. Phenylephrine has significant alpha adrenergic effects (vasoconstriction and pupillary dilation) and minimal effects on beta receptors. When used alone, phenylephrine is reportedly not efficacious in the cat unless used with other mydriatics.

storage

Desiccate at RT

(R)-Phenylephrine Hydrochlorid(61-76-7)Related Product Information

• Ethyl acetate
• Topotecan hydrochloride
• Ursodeoxycholic acid
• Isoprenaline hydrochloride
• Epinephrine Hydrochloride
• Benzyl alcohol
• L(-)-Epinephrine
• CHLOROPHOSPHONAZO III
• Chenodeoxycholic acid
• DL-NORPHENYLEPHRINE HYDROCHLORIDE
• N-methyl-5,6-dihydroxyindole
• 2,2-Dichloro-1-(3-hydroxyphenyl)-ethanone
• N-(2-Succinyl) Phenylephrine
• Phenylephrine Impurity 32
• N-ACETYL-4-BENZOQUINONE IMINE
• 1,2,3,4-Tetrahydro-4,6-dihydroxy-2-methyl-isoquinoline
• 3-Hydroxy-4-[[(2R)-2-hydroxy-2-(3-hydroxyphenyl)ethyl]MethylaMino]-4-oxo-butanoic Acid
• Phenylephrine EP Impurity D
• Phenylephrine Hcl