Phenylephrine Hydrochloride

Base Information

• Chemical Name: Phenylephrine Hydrochloride
• CAS No.: 61-76-7
• Deprecated CAS: 50741-76-9,644-22-4,827-62-3,644-22-4,827-62-3
• Molecular Formula: C9H14ClNO2
• Molecular Weight: 203.669
• Hs Code.: 29225090
• European Community (EC) Number: 200-517-3
• NSC Number: 757273
• UNII: 04JA59TNSJ
• DSSTox Substance ID: DTXSID3021142
• Wikidata: Q27107758
• NCI Thesaurus Code: C29363
• RXCUI: 8164
• ChEMBL ID: CHEMBL1200339
• Mol file: 61-76-7.mol

Synonyms:(R)-3-Hydroxy-alpha-((methylamino)methyl)benzenemethanol;Metaoxedrin;Metasympatol;Mezaton;Neo Synephrine;Neo-Synephrine;Neosynephrine;Phenylephrine;Phenylephrine Hydrochloride;Phenylephrine Tannate;Tannate, Phenylephrine

Chemical Property of Phenylephrine Hydrochloride

Chemical Property:

• Appearance/Colour: white to almost white crystalline powder
• Melting Point: 143-145 °C(lit.)
• Refractive Index: -45.5 ° (C=1, H2O)
• Boiling Point: 341.1 °C at 760 mmHg
• PKA: pK1 8.77; pK2 9.84(at 25℃)
• Flash Point: 163.4 °C
• PSA: 52.49000
• LogP: 1.83790
• Storage Temp.: Desiccate at RT
• Solubility.: Freely soluble in water and in ethanol (96 per cent).
• Water Solubility.: >=10 g/100 mL at 21 ºC
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 203.0713064
• Heavy Atom Count: 13
• Complexity: 130

Purity/Quality:

98%99% ^*data from raw suppliers

(R)-(?)-Phenylephrine hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,T,F
• Statements: 22-36/37/38-39/23/24/25-23/24/25-11
• Safety Statements: 26-36-37/39-45-36/37-16-7

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CNCC(C1=CC(=CC=C1)O)O.Cl
• Isomeric SMILES: CNC[C@@H](C1=CC(=CC=C1)O)O.Cl
• Recent ClinicalTrials: Sex Differences in Sympathetic Vascular Reactivity at High Altitude
• Recent EU Clinical Trials: Prospective intraindividual comparison of the mydriasis of a standardized intracameral anaesthetics with the topical preoperative drop application
• 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). 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.
• 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. DECONGESTANTS (R)-Phenylephrine Hydrochloride is an α-Adrenergic agonist. Mydriatic; decongestant.

Technology Process of Phenylephrine Hydrochloride

There total 25 articles about Phenylephrine Hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

methylamine (74-89-5) + 3-((R)-1-Hydroxy-2-iodo-ethyl)-phenol (603983-68-2) → phenylephrine hydrochloride (61-76-7,827-62-3)

Guidance literature:

methylamine; 3-((R)-1-Hydroxy-2-iodo-ethyl)-phenol; In tetrahydrofuran; water; at 20 ℃; for 3h;

With hydrogenchloride; at 20 ℃;

DOI:10.1016/S0040-4039(03)01554-5

Reference yield: 90.0%

C13H21NO4 → phenylephrine hydrochloride (61-76-7,827-62-3)

Guidance literature:

With hydrogenchloride; In methanol; for 1h; Reflux;

DOI:10.1021/op970128+

Reference yield: 85.0%

3-Hydroxyphenyl-ω-methylaminoacetophenone hydrochloride (94240-17-2) → phenylephrine hydrochloride (61-76-7,827-62-3)

Guidance literature:

With hydrogen; [Rh(cod)(R-Binapine)]BF₄; In methanol; at 65 ℃; for 18.25h; under 21752.2 - 24752.5 Torr; Product distribution / selectivity;

upstream raw materials:

(R)-2-(Benzyl-methyl-amino)-1-(3-benzyloxy-phenyl)-ethanol; hydrochloride

methylamine

3-((R)-1-Hydroxy-2-iodo-ethyl)-phenol

3-(tert-butyl-dimethyl-sylanyloxy)benzaldehyde

Downstream raw materials:

(-)-m-octopamine

(3aR,5aR,9bS)-3a-hydroxy-3-((((2R)-2-hydroxy-2-(3-hydroxyphenyl)ethyl)(methyl)amino)methyl)-5a,9-dimethyl-3,3a,4,5,5a,6,7,8-octahydronaphtho[1,2-b]furan-2(9bH)-one

tert-butyl [(2R)-2-hydroxy-2-(3-hydroxyphenyl)ethyl](methyl)carbamate

5-(3-hydroxyphenyl)-3-methyl-2-oxazolidone

Refernces

• 1、 Dai, Shuangxiong,Li, Guohua,Zhang, Wenbo,Zhang, Cuiyan,Song, Xiaoling,Huang, Di. "Efficient synthesis of (R)-phenylephrine using a polymer-supported Corey-Bakshi-Shibata catalyst". supporting information. p. 740 - 743. Retrieved 2017/05/16.
• 2、 McGarrity, John F.,Zanotti-Gerosa, Antonio. "A feasibility study on the synthesis of phenylephrine via ruthenium-catalyzed homogeneous asymmetric hydrogenation". experimental part. p. 2479 - 2486. Retrieved 2011/02/22.