(R)-Phenylephrine Hydrochlorid

(R)-Phenylephrine Hydrochlorid Basic information
Product Name:(R)-Phenylephrine Hydrochlorid
Synonyms:(-)-3-[1(R)-Hydroxy-2-(methylamino)ethyl]phenol hydrochloride;Phenylephrine Hydrochloride (200 mg);PHENYLEPHRINE HCL BP ((R)-3-HYDROXY-ALPHA-(METHYLAMINO) METHYL] BENZENEMETHANOLHYDROCHL ORIDE);(-)-3-HYDROXY-ALPHA-(METHYLAMINOMETHYL)BENZYL ALCOHOL HYDROCHLORIDE;L-1-(M-HYDROXYPHENYL)-2-METHYLAMINOETHANOL HYDROCHLORIDE;L-(3-HYDROXYPHENYL)-N-METHYLETHANOLAMINEHYDROCHLORIDE;L-A-HYDROXY-B-METHYLAMINO-3-HYDROXY-1-ETHYLBENZENE HYDROCHLORIDE;L(-)-PHENYLEPHRINE HCL
CAS:61-76-7
MF:C9H13NO2.ClH
MW:203.67
EINECS:200-517-3
Product Categories:Adrenergic Agents;AFRIN;Amines;Aromatics;Chiral Reagents;API;Intermediates & Fine Chemicals;Pharmaceuticals;pharmaceutical raw material;Pharmaceutical intermediates;61-76-7
Mol File:61-76-7.mol
(R)-Phenylephrine Hydrochlorid Structure
(R)-Phenylephrine Hydrochlorid Chemical Properties
Melting point 143-145 °C(lit.)
alpha -47 º (c=2, H2O)
refractive index -45.5 ° (C=1, H2O)
Fp 9℃
storage temp. 2-8°C
solubility Freely soluble in water and in ethanol (96 per cent).
form Crystalline Powder
pkapK1 8.77; pK2 9.84(at 25℃)
color White to almost white
PHpH (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 Reference61-76-7(CAS DataBase Reference)
EPA Substance Registry SystemPhenylephrine 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
ToxicityLD50 in rats (mg/kg): 17 ±1.1 i.p.; 33 ±2.0 s.c. (Warren, Werner)
MSDS Information
(R)-Phenylephrine Hydrochlorid Usage And Synthesis
DescriptionR-(-)-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.
Chemical PropertiesPhenylephrine 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 Propertieswhite to almost white crystalline powder
OriginatorNeosynephrine, Badrial, France ,1953
UsesPhenylephrine 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.
UsesDECONGESTANTS
Uses(R)-Phenylephrine Hydrochloride is an α-Adrenergic agonist. Mydriatic; decongestant.
DefinitionChEBI: A hydrochloride that is the monohydrochloride salt of phenylephrine.
Manufacturing Process4.5 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 nameAfrin 4 Hour Nasal Spray (Schering-Plough Health Care); Biomydrin (Parke-Davis); Mydfrin (Alcon); Neo-Synephrine (Sterling Health U.S.A.); Nostril (Boehringer Ingelheim).
Therapeutic FunctionAdrenergic
General DescriptionOdorless white microcrystalline powder. Bitter taste. pH (1% aqueous solution) about 5.
Air & Water ReactionsMay be sensitive to prolonged exposure to air and light. Water soluble.
Reactivity ProfilePhenylephrine hydrochloride is incompatible with acids, acid chlorides, acid anhydrides and oxidizing agents. Phenylephrine hydrochloride is also incompatible with butacaine, alkalis and ferric salts.
Fire HazardFlash point data for Phenylephrine hydrochloride are not available; however, Phenylephrine hydrochloride is probably combustible.
Biological Activityα 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 allergensPhenylephrine hydrochloride is an alpha-adrenergic agonist, used as a mydriatic and decongestant in eyedrops.
Safety ProfilePoison 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 TreatmentsPhenylephrine 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.
storageDesiccate at RT
(R)-Phenylephrine Hydrochlorid Preparation Products And Raw materials
Raw materialsDiethyl ether-->Toluene-->Benzyl alcohol-->Hydrogen-->Hydrochloric acid
Preparation ProductsN-Boc-(R)-Phenylephrine
Phenylephrine Naxagolide Ursodeoxycholic acid (1R,2S)-(-)META-HYDROXYEPHEDRINE HYDROCHLORIDE Topotecan hydrochloride Benzyl alcohol (R)-A,A-BIS(3-METHOXYPHENYL)-2-PYRROLIDINEMETHANOL HYDROCHLORIDE Chenodeoxycholic acid (-)-2-[METHYLAMINO]-1-PHENYLPROPANE Isoprenaline hydrochloride Epinephrine Hydrochloride Phenylephrine hydrochloride N-[(1R,2R)-1,2,3,4-TETRAHYDRO-1-HYDROXY-7-METHOXY-2-NAPHTHALENYL]-CHLOROACETAMIDE Ethyl acetate Benzyl L(-)-Epinephrine DL-PHENYLEPHRINE HYDROCHLORIDE CHLOROPHOSPHONAZO III Phenylephrine Hcl

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