(R)-Phenylephrine Hydrochlorid
- Iupac Name：hydron;3-[(1R)-1-hydroxy-2-(methylamino)ethyl]phenol;chloride
- CAS No.: 61-76-7
- Molecular Weight：203.666
- Modify Date.: 2022-11-29 11:23
- Introduction: Odorless white microcrystalline powder. Bitter taste. pH (1% aqueous solution) about 5.
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1. Names and Identifiers
- 1.1 Name
- (R)-Phenylephrine Hydrochlorid
- 1.2 Synonyms
(-)-3-[1(R)-Hydroxy-2-(methylamino)ethyl]phenol hydrochloride (R)-(-)-Phenylephrine (hydrochloride) (R)-3-Hydroxy-a-[(methylamino)methyl]benzenemethanol Hydrochloride )-3-Hydroxy-α-(methylaminomethyl)benzyl alcohol hydrochloride
(R)-(?Phenylephring Hydrochloride
(R)-(?(-)-3-HYDROXY-ALPHA-(METHYLAMINOMETHYL)BENZYL ALCOHOL HYDROCHLORIDE 1-m-Hydroxy-a-[(methylamino)methyl]benzyl Alcohol Hydrochloride 3-[(1R)-1-hydroxy-2-(méthylamino)éthyl]phénol chlorhydrate 3-[(1R)-1-Hydroxy-2-(methylamino)ethyl]benzololhydrochlorid 3-[(1R)-1-Hydroxy-2-(methylamino)ethyl]phenol hydrochloride (1:1) AK-Dilate AK-Nefrin almefrin benzenemethanol, 3-hydroxy-α-[(methylamino)methyl]-, (αR)-, hydrochloride Benzenemethanol, 3-hydroxy-α-[(methylamino)methyl]-, (αR)-, hydrochloride (1:1) consdrin efricel EINECS 200-517-3 emagrin fenilfar fenox Isophrin L-(3-HYDROXYPHENYL)-N-METHYLETHANOLAMINEHYDROCHLORIDE L-1-(M-HYDROXYPHENYL)-2-METHYLAMINOETHANOL HYDROCHLORIDE l-a-Hydroxy-b-methylamino-3-hydroxy-1-ethylbenzene Hydrochloride lexatol Metaoxedrin Mezaton MFCD00012605 m-Sympatol phenylephrine HCl PHENYLEPHRINE HCL BP ((R)-3-HYDROXY-ALPHA-(METHYLAMINO) METHYL] BENZENEMETHANOLHYDROCHL ORIDE) Phenylephrine hydrochloride Phenylephrine Hydrochloride (200 mg) Pyracort D rhinall synasal uri
- 1.3 CAS No.
- 61-76-7
- 1.4 CID
- 657210
- 1.5 EINECS(EC#)
- 200-517-3
- 1.6 Molecular Formula
- C9H14ClNO2 (isomer)
- 1.7 Inchi
- InChI=1S/C9H13NO2.ClH/c1-10-6-9(12)7-3-2-4-8(11)5-7;/h2-5,9-12H,6H2,1H3;1H/t9-;/m0./s1
- 1.8 InChkey
- OCYSGIYOVXAGKQ-FVGYRXGTSA-N
- 1.9 Canonical Smiles
- [H+].CNCC(C1=CC(=CC=C1)O)O.[Cl-]
- 1.10 Isomers Smiles
- [H+].CNC[C@@H](C1=CC(=CC=C1)O)O.[Cl-]
2. Properties
- 2.1 Melting point
- 140-145℃
- 2.1 Boiling point
- 341.1 °C at 760 mmHg
- 2.1 Refractive index
- -45.5 ° (C=1, H2O)
- 2.1 Flash Point
- 163.4 °C
- 2.1 Precise Quality
- 203.07100
- 2.1 PSA
- 52.49000
- 2.1 logP
- 1.83790
- 2.1 Solubility
- >=10 g/100 mL at 21 oC
- 2.2 Appearance
- White to almost white Crystalline Powder
- 2.3 Chemical Properties
- white to almost white crystalline powder
- 2.4 Color/Form
- White to almost white
- 2.5 Contact Allergens
- Phenylephrine hydrochloride is an alpha-adrenergicagonist, used as a mydriatic and decongestant ineyedrops.
- 2.6 PH
- pH (10g/L, 25℃) : 4.5～5.5
- 2.7 pKa
- pK1 8.77; pK2 9.84(at 25℃)
- 2.8 Water Solubility
- >=10 g/100 mL at 21 oC
- 2.9 Spectral Properties
- MAX ABSORPTION (PH 9.4 BORATE BUFFER): 237 NM (A= 258, 1%, 1 CM); 291 NM (A= 140, 1%, 1 CM); MAX ABSORPTION (0.2 M H3BO3): 272 NM (A= 83, 1%, 1 CM)
- 2.10 StorageTemp
- 2-8°C
3. Use and Manufacturing
- 3.1 Definition
- ChEBI: A hydrochloride that is the monohydrochloride salt of phenylephrine.
- 3.2 General Description
- Odorless white microcrystalline powder. Bitter taste. pH (1% aqueous solution) about 5.
- 3.3 Usage
- 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.
4. Safety and Handling
- 4.1 Symbol
- GHS07
- 4.1 Hazard Codes
- Xn
- 4.1 Signal Word
- Warning
- 4.1 Risk Statements
- R22;R36/37/38
- 4.1 Safety Statements
- S26;S37/39
- 4.1 Exposure Standards and Regulations
- The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl phenylephrine hydrochloride, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Phenylephrine Hydrochloride/
Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: phenylephrine hydrochloride (less than 0.08 percent) is included in ophthalmic vasoconstrictor drug products. /Phenylephrine hydrochloride/
Nasal decongestant active active ingredients. The active ingredient of the product consists of any of the following when used in the dosage limits and in the dosage forms established for each ingredient. Oral nasal decongestants: phenylephrine hydrochloride, phenylephrine bitartrate in an effervescent dosage form. Topical nasal decongestants: Phenylephrine hydrochloride. /Phenylephrine hydrochloride; Phenylephrine bitartrate/
Vasoconstrictor active ingredients. The active ingredient of the product consists of any of the following when used in the concentration or within the concentration range established for each ingredient. Phenylephrine hydrochloride 0.25 percent.
Ophthalmic vasoconstrictors. The active ingredient of the product consists of one of the following, within the established concentration for each ingredient. Phenylephrine hydrochloride, 0.08 to 0.2 percent.
- 4.2 Packing Group
- III
- 4.2 Octanol/Water Partition Coefficient
- log Kow = -0.31 (est)
- 4.3 Fire Hazard
- Flash point data for Phenylephrine hydrochloride are not available; however, Phenylephrine hydrochloride is probably combustible.
- 4.4 Hazard Class
- 6.1(b)
- 4.4 Hazard Declaration
- H302-H315-H319-H335
- 4.4 DisposalMethods
- SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
- 4.5 RIDADR
- UN 3249
- 4.5 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.
- 4.6 Caution Statement
- P261-P305 + P351 + P338
- 4.6 Formulations/Preparations
- Oral: Strips, orally dissolving: 1.25 mg Triaminic Infant Thin Strips Decongestant, (Novartis) 2.5 mg Triaminic Thin Strips Cold, (Novartis). Tablets: 10 mg Sudafed PE, (Pfizer). Parenteral: Injection: 10 mg/mL Neo-Synephrine Hydrochloride (with sodium metabisulfite), (Sanofi-Aventis), Phenylephrine Hydrochloride Injection, (American Regent), Phenylephrine Hydrochloride Injection, (Baxter). Topical: Cream: 0.25% with Glycerin 12%, (Petrolatum); 18%, and Shark Liver Oil 3% Preparation H (with cetyl alcohol, methylparaben, and stearyl alcohol), (Wyeth). Gel: 0.25% with Witch Hazel 50% Preparation H (with methylparaben and propylparaben), (Wyeth). Ointment: 0.25% with Mineral Oil 14%, Petrolatum 71.9%, and Shark Liver Oil 3% Preparation H (with methylparaben and propylparaben), (Wyeth). Suppository: 0.25% with Cocoa Butter 85.5% and Shark Liver Oil 3% Preparation H (with methylparaben and propylparaben), (Wyeth).
Nasal: Solution: 0.25% Neo-Synephrine Mild Formula Spray (with benzalkonium chloride), (Bayer); 0.5% Neo-Synephrine Regular Strength (with benzalkonium chloride; drops and spray), (Bayer), Vicks Sinex for Sinus Relief (with benzalkonium chloride; regular or metered pump mist spray), (Procter & Gamble); 1% Neo-Synephrine Extra Strength (with benzalkonium chloride; drops and spray), (Bayer). Ophthalmic: Solution: 0.12% Ocu-Phrin, Ocumed Relief (with benzalkonium chloride), (Allergan); 2.5% AK-Dilate (with benzalkonium chloride and sodium bisulfite), (Akorn), Mydfrin (with benzalkonium chloride and sodium bisulfite), (Alcon) Neo-Synephrine Hydrochloride (with benzalkonium chloride), (Sanofi-Aventis), Ocu-Phrin, (Ocumed); 10% AK-Dilate (with benzalkonium chloride and sodium bisulfite), (Akorn), Neo-Synephrine Hydrochloride (with benzalkonium chloride; plain and viscous), (Sanofi-Aventis), Ocu-Phrin, (Ocumed). Parenteral: Injection: 10 mg/mL Neo-Synephrine Hydrochloride (with sodium metabisulfite), (Sanofi-Aventis), Phenylephrine Hydrochloride Injection, (American Regent), Phenylephrine Hydrochloride Injection, (Baxter). /Phenylephrine hydrochloride/
Ophthalmic: Solution: 0.12% Ocu-Phrin, (Ocumed), Relief (with benzalkonium chloride; viscous), (Allergan); 2.5% AK-Dilate (with benzalkonium chloride and sodium bisulfite), (Akorn), Mydfrin (with benzalkonium chloride and sodium bisulfite), (Alcon), Neo-Synephrine Hydrochloride (with benzalkonium chloride), (Sanofi-Aventis), Ocu-Phrin, (Ocumed), Phenylephrine Hydrochloride Ophthalmic Solution, (Bausch & Lomb), Phenylephrine Hydrochloride Ophthalmic Solution, (Falcon); 10% AK-Dilate (with benzalkonium chloride and sodium bisulfite), (Akorn), Neo-Synephrine Hydrochloride (with benzalkonium chloride; plain and viscous), (Sanofi-Aventis), Ocu-Phrin, (Ocumed). /Phenylephrine hydrochloride/
- 4.7 WGK Germany
- 3
- 4.7 RTECS
- DO7525000
- 4.7 Safety
- Hazard Codes:Xn
Risk Statements:22-36/37/38
22:Harmful if swallowed
36/37/38:Irritating to eyes, respiratory system and skin
Safety Statements:26-36-37/39
26:In case of contact with eyes, rinse immediately with plenty
of water and seek medical advice
36:Wear suitable protective clothing
37/39:Wear suitable protective clothing, gloves and eye/face
protection
RIDADR:3249
WGK Germany:3
HazardClass:6.1(b)
PackingGroup:III
- 4.8 Specification
-
white to almost white crystalline powder
usageEng:α-Adrenergic agonist. Mydriatic; decongestant.
Safety Statements:26-36-37/39
26:In case of contact with eyes, rinse immediately with plenty
of water and seek medical advice
36:Wear suitable protective clothing
37/39:Wear suitable protective clothing, gloves and eye/face
protection
- 4.9 Toxicity
- LD50 in rats (mg/kg): 17 ±1.1 i.p.; 33 ±2.0 s.c. (Warren, Werner)
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Acute toxicity - Oral, Category 4
Skin sensitization, Category 1B
Hazardous to the aquatic environment, short-term (Acute) - Category Acute 2
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |  |
| Signal word | Warning |
| Hazard statement(s) | H302 Harmful if swallowed H317 May cause an allergic skin reaction H401 Toxic to aquatic life |
| Precautionary statement(s) | |
| Prevention | P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P272 Contaminated work clothing should not be allowed out of the workplace. P280 Wear protective gloves/protective clothing/eye protection/face protection. P273 Avoid release to the environment. |
| Response | P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P333+P313 If skin irritation or rash occurs: Get medical advice/attention. P321 Specific treatment (see ... on this label). P362+P364 Take off contaminated clothing and wash it before reuse. |
| Storage | none |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
61-76-7Total: 1 Synthesis Route
8. Other Information
- 8.0 Merck
- 14,7286
- 8.1 BRN
- 4158948
- 8.2 Target
- Value
- 8.3 Description
- R-(-)-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).1 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 (Item No. 16673).2 This compound is frequently used to precontract smooth muscle in preparations designed to study the properties of various vasodilator agents.3,4
- 8.4 Chemical Properties
- white to almost white crystalline powder
- 8.5 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.
- 8.6 Originator
- Neosynephrine, Badrial, France ,1953
- 8.7 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.
- 8.8 Uses
- α-Adrenergic agonist. Mydriatic; decongestant.
- 8.9 Uses
- DECONGESTANTS
- 8.10 Uses
- (R)-Phenylephrine Hydrochloride is an α-Adrenergic agonist. Mydriatic; decongestant.
- 8.11 Definition
- ChEBI: A hydrochloride that is the monohydrochloride salt of phenylephrine.
- 8.12 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.
- 8.13 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).
- 8.14 Therapeutic Function
- Adrenergic
- 8.15 General Description
- Odorless white microcrystalline powder. Bitter taste. pH (1% aqueous solution) about 5.
- 8.16 Air & Water Reactions
- May be sensitive to prolonged exposure to air and light. Water soluble.
- 8.17 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.
- 8.18 Fire Hazard
- Flash point data for Phenylephrine hydrochloride are not available; however, Phenylephrine hydrochloride is probably combustible.
- 8.19 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.
- 8.20 Contact allergens
- Phenylephrine hydrochloride is an alpha-adrenergic agonist, used as a mydriatic and decongestant in eyedrops.
- 8.21 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.
- 8.22 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.
9. Computational chemical data
- Molecular Weight: 203.666g/mol
- Molecular Formula: C9H14ClNO2
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 203.0713064
- Monoisotopic Mass: 203.0713064
- Complexity: 130
- Rotatable Bond Count: 3
- Hydrogen Bond Donor Count: 4
- Hydrogen Bond Acceptor Count: 4
- Topological Polar Surface Area: 52.5
- Heavy Atom Count: 13
- Defined Atom Stereocenter Count: 1
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 3
- CACTVS Substructure Key Fingerprint: AAADccByMAAEAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAAHgAQCAAADBThmAYyBoLAAgCAAiBCAAACAAAgIAAIiIAOCIgKNiKCkROEcAAk0BEYmAfQ0LIOAAABAAAAAAAAAAIAAAAAAAAAAAAAAA==
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11. Realated Product Infomation
skype
1YR
