61-76-7 Usage
Chemical Properties
Different sources of media describe the Chemical Properties of 61-76-7 differently. You can refer to the following data:
1. white to almost white crystalline powder
2. 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.
Originator
Neosynephrine, Badrial, France ,1953
Uses
Different sources of media describe the Uses of 61-76-7 differently. You can refer to the following data:
1. 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.
2. DECONGESTANTS
3. (R)-Phenylephrine Hydrochloride is an α-Adrenergic agonist. Mydriatic; decongestant.
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).
General Description
Odorless white microcrystalline powder. Bitter taste. pH (1% aqueous solution) about 5.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 61-76-7 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 1 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 61-76:
(4*6)+(3*1)+(2*7)+(1*6)=47
47 % 10 = 7
So 61-76-7 is a valid CAS Registry Number.
InChI:InChI=1/C9H13NO2.2ClH/c1-10-6-9(12)7-3-2-4-8(11)5-7;;/h2-5,9-12H,6H2,1H3;2*1H/t9-;;/m0../s1
61-76-7Relevant articles and documents
Preparation method of L-phenylephrine hydrochloride
-
, (2020/10/04)
The invention relates to a preparation method of L-phenylephrine hydrochloride, and specifically discloses a preparation method of L-phenylephrine hydrochloride, which comprises the steps of chlorination reaction, chiral reduction reaction, amination salifying and recrystallization. The preparation method has the advantages of cheap and easily available raw materials, simple operation process, loweconomic cost, high product yield and the like, and the product quality meets the standard requirements of Chinese Pharmacopoeia and European Pharmacopoeia.
Efficient synthesis of (R)-phenylephrine using a polymer-supported Corey-Bakshi-Shibata catalyst
Dai, Shuangxiong,Li, Guohua,Zhang, Wenbo,Zhang, Cuiyan,Song, Xiaoling,Huang, Di
, p. 740 - 743 (2017/05/16)
An efficient and mild synthetic route to (R)-phenylephrine hydrochloride using Corey-Bakshi-Shibata (CBS) catalyst was reported. In order to avoid a lengthy recovery process of the catalyst from homogeneous reaction, a polymer-supported CBS catalyst was prepared, and a preliminary attempt was made to achieve a continuous reduction on a laboratory scale, which contributes to synthesis of (R)-phenylephrine in a cost-effective way.
PROCESS FOR RESOLUTION OF 1-(3-HYDROXYPHENYL)-2-METHYLAMINO ETHANOL
-
, (2012/05/07)
Resolution of the title compound to its active isomer (R)-1-(3-hydroxyphenyl)-2-methylamino ethanol with (R)-naproxen as a resolving agent.
A feasibility study on the synthesis of phenylephrine via ruthenium-catalyzed homogeneous asymmetric hydrogenation
McGarrity, John F.,Zanotti-Gerosa, Antonio
experimental part, p. 2479 - 2486 (2011/02/22)
We report a feasibility study on a new route to (R)-phenylephrine, based on the ruthenium-catalyzed asymmetric hydrogenation of an aminoketone precursor. The direct and fast asymmetric reduction of aminoketones or their hydrochloride salts is achievable at low catalyst loadings (molar substrate to catalyst ratio, S/C, >25,000/1, TOF up to 25,000 h-1) with high enantioselectivity (>95% ee), without the need for N-protection nor isolation of the free base prior to reaction.
PROCESS FOR THE PREPARATION OF OPTICALLY ACTIVE 2-AMINO-1-PHENYLETHANOLS
-
Page/Page column 14, (2008/12/08)
Optically active 2-amino-l-phenylethanols of formula (I) or its mirror image, wherein R1 is C1-6 alkyl or aryl-substituted C1-6 alkyl and R2 through R6 are independently hydrogen, hydroxy or C1-6 alkoxy, or salts thereof are prepared by asymmetric hydrogenation of the corresponding 2-aminoaceto-phenones in the presence of a rhodium complex catalyst comprising a chiral diphosphine ligand, wherein each phosphorus atom is part of a heterocyclic ring system which contains at least one chiral carbon atom directly bound to the phosphorus atom.
PROCESS FOR THE PREPARATION OF OPTICALLY ACTIVE 2-AMINO-1-PHENYLETHANOLS
-
Page/Page column 12, (2008/12/06)
Optically active 2-amino-l-phenylethanols of formula (I) or its mirror image, wherein R1 is hydrogen, C1-6alkyl or aryl-substituted C1-6alkyl and R2 through R6 are independently hydrogen, hydroxy or C1-6alkoxy, or salts thereof are prepared by asymmetric hydrogenation of the corresponding 2-aminoacetophenones in the presence of a ruthenium complex catalyst comprising a chiral phosphine ligand.
Oral pharmaceutical compositions containing cyclodextrins as taste masking agent
-
, (2008/06/13)
The application discloses oral pharmaceutical compositions which are tasted in the mouth during administration. Fast-dissolving tablets, chewable tablets and effervescent dispersions are exemplified. To mask the taste of unpleasant-tasting active ingredients, it has been found that blending with cyclodextrin without the conventional complex formation is effective. Consequently more economical modes of manufacture such as simple granulation and dry blending can be used.
Enantioselective synthesis of (R)-phenylephrine hydrochloride
Pandey, Rajesh Kumar,Upadhyay, Puspesh Kumar,Kumar, Pradeep
, p. 6245 - 6246 (2007/10/03)
An efficient method for the synthesis of enantiomerically pure (R)-phenylephrine hydrochloride 1 is described using a Sharpless asymmetric dihydroxylation as the key step.
Method for preparing of L-phenylephrine hydrochloride
-
, (2008/06/13)
The present invention relates to an improved process for preparing L-phenylephrine hydrochloride 3 on an industrial scale by asymmetric hydrogenation as the key step and a special sequence of subsequent steps, using [Rh(COD)Cl]2 as catalyst and a chiral, two-pronged phosphine ligand such as (2R,4R)-4-(dicyclohexylphosphino)-2-(diphenylphosphino-methyl)-N-methyl-aminocarbonyl-pyrrolidine as the catalyst system.
A practical synthesis of (R)-(-)-phenylephrine hydrochloride
Gurjar, Mukund K.,Krishna, L. Murali,Sarma, Bugga V.N.,Chorghade, Mukund S.
, p. 422 - 424 (2013/09/08)
(R)-(-)-Phenylephrine hydrochloride is a clinically potent adrenergic agent and β-receptor sympathomimetic drug, exclusively marketed in the optically active form. An asymmetric synthesis has been developed with high enantiomeric excess based on hydrolytic kinetic resolution of a styrene oxide derivative using (R,R)-SalenCoIIIOAc complex.
