Phenylephrine

Base Information

• Chemical Name: Phenylephrine
• CAS No.: 59-42-7
• Molecular Formula: C9H13NO2
• Molecular Weight: 167.208
• European Community (EC) Number: 200-424-8,215-810-1
• UNII: 1WS297W6MV
• DSSTox Substance ID: DTXSID9023465
• Nikkaji Number: J8.601K
• Wikipedia: Phenylephrine
• Wikidata: Q421910
• NCI Thesaurus Code: C62067
• RXCUI: 8163
• Pharos Ligand ID: RDLQTF8DU779
• Metabolomics Workbench ID: 38062
• ChEMBL ID: CHEMBL1215
• Mol file: 59-42-7.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

Chemical Property:

• Vapor Pressure: 3.18E-05mmHg at 25°C
• Melting Point: 171°C
• Refractive Index: -55.5 ° (C=5, 1mol/L HCl)
• Boiling Point: 341.1 °C at 760 mmHg
• PKA: pKa 8.9 (Uncertain)
• Flash Point: 163.4 °C
• PSA: 52.49000
• Density: 1.159 g/cm³
• LogP: 1.03590
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Slightly soluble in water, sparingly soluble in methanol, slightly soluble in ethanol (96 per cent). It dissolves in dilute mineral acids and in dilute solutions of alkali hydroxides.
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 167.094628657
• Heavy Atom Count: 12
• Complexity: 130

Purity/Quality:

99% ^*data from raw suppliers

L-Phenylephrine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38-41-37/38
• Safety Statements: 26-36-45-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNCC(C1=CC(=CC=C1)O)O
• Isomeric SMILES: CNC[C@@H](C1=CC(=CC=C1)O)O
• Recent ClinicalTrials: POTS Adrenergic Ab (CIHR Aims #1&2)
• Recent EU Clinical Trials: Influence of continuous administration of phenylephrine versus dobutamine on spinal oxygen saturation, measured with near-infrared spectroscopy (NIRS).
• Recent NIPH Clinical Trials: Development and evaluation of a new method to determine baroreflex sensitivity, and its application to clinical investigations
• Description: This synthetic drug has both chemical and pharmacological similarities to norepinephrine. A characteristic quality of phenylephrine is the distinctly expressed selectivity to α- adrenoreceptors, especially α1-adrenoreceptors. Although phenylephrine increases the contractibility of blood vessels, in practical terms it is not considered a cardiostimulant.
• Uses: L-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. Because L-phenylephrine acts on adrenergic α1 receptors in the arterioles of the nasal mucosa to produce constriction, it has been examined clinically as an oral decongestant. Phenylephrine is used in hypotension, paroxysmal supraventricular tachycardia, and shock. It is also used locally, particularly in the form of nasal spray, for relieving edema.
• Clinical Use: Phenylephrine is a potent direct-acting α1-agonist with clinical effects similar to those of noradrenaline. It causes widespread vasoconstriction with an increase in arterial pressure, reflex bradycardia and decrease in cardiac output. It may be administered by i.v. bolus (50–100μg boluses) and i.v. infusion (50–150μgmin –1) to maintain arterial pressure during general anaesthesia or other causes of low SVR. It may also be used topically as a nasal decongestant or mydriatic. There is some evidence suggesting a paradoxical reduction in cerebral oxygen delivery.

Technology Process of Phenylephrine

There total 13 articles about Phenylephrine 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: 99.0%

(S)-phenylephrine (614-03-9) → Phenylephrin (59-42-7)

Guidance literature:

(S)-phenylephrine; With sulfuric acid; acetic anhydride; at 105 ℃; for 12h;

With water; at 95 ℃; for 3h; optical yield given as %ee; enantioselective reaction;

DOI:10.1016/j.procbio.2010.06.003

Reference yield: 92.0%

→ 1,3-oxazolidine (504-76-7) + Phenylephrin (59-42-7)

Guidance literature:

Reference yield: 90.0%

(R)-phenylephrine-(R)-naproxen (1280541-42-5) → Phenylephrin (59-42-7)

Guidance literature:

(R)-phenylephrine-(R)-naproxen; With hydrogenchloride; In water; toluene; at 75 - 80 ℃; for 0.5h; pH=< 2;

With ammonium hydroxide; In water; at 1 - 15 ℃; pH=~ 9; Product distribution / selectivity;

upstream raw materials:

(S)-phenylephrine

Phenylephrine

3-Hydroxyphenyl-ω-methylaminoacetophenone hydrochloride

α-methylamino-m-hydroxy-acetophenone sulfate

Downstream raw materials:

(-)-1-acetoxy-1-(3-acetoxy-phenyl)-2-methylamino-ethane

1-{(R)-2-Hydroxy-2-[3-(quinolin-2-ylmethoxy)-phenyl]-ethyl}-1,3-dimethyl-urea

3-Ethyl-1-{(R)-2-hydroxy-2-[3-(quinolin-2-ylmethoxy)-phenyl]-ethyl}-1-methyl-urea

Ethyl-carbamic acid (R)-2-(3,3-diethyl-1-methyl-ureido)-1-[3-(quinolin-2-ylmethoxy)-phenyl]-ethyl ester

Refernces

• 1、 Tokoshima, Daisuke,Hanaya, Kengo,Shoji, Mitsuru,Sugai, Takeshi. "Whole-cell yeast-mediated preparation of (R)-2-chloro-1-(3-nitrophenyl) ethanol as a synthetic precursor for (R)-phenylephrine". . p. 95 - 99. Retrieved 2013/10/01.
• 2、 Kureshy, Rukhsana I.,Dangi, Balchand,Das, Anjan,Khan, Noor-Ul H.,Abdi, Sayed H.R.,Bajaj, Hari C.. "Recyclable Cu(II)-macrocyclic salen complexes catalyzed nitroaldol reaction of aldehydes: A practical strategy in the preparation of (R)-phenylephrine". . p. 74 - 79. Retrieved 2012/10/07.