Epinephrine

Base Information

• Chemical Name: Epinephrine
• CAS No.: 51-43-4
• Deprecated CAS: 51028-73-0
• Molecular Formula: C9H13NO3
• Molecular Weight: 183.207
• Hs Code.: 29373100
• European Community (EC) Number: 200-098-7
• UN Number: 2811
• UNII: YKH834O4BH
• DSSTox Substance ID: DTXSID5022986
• Nikkaji Number: J9.224J
• Wikipedia: Adrenaline
• Wikidata: Q132621
• NCI Thesaurus Code: C74941,C2292
• RXCUI: 3992
• Pharos Ligand ID: YGMZR3UB1NMG
• Metabolomics Workbench ID: 37056
• ChEMBL ID: CHEMBL679
• Mol file: 51-43-4.mol

Synonyms:4-(1-Hydroxy-2-(methylamino)ethyl)-1,2-benzenediol;Acetate, Epinephrine;Adrenaline;Adrenaline Acid Tartrate;Adrenaline Bitartrate;Adrenaline Hydrochloride;Epifrin;Epinephrine;Epinephrine Acetate;Epinephrine Bitartrate;Epinephrine Hydrochloride;Epinephrine Hydrogen Tartrate;Epitrate;Lyophrin;Medihaler-Epi

Chemical Property of Epinephrine

Chemical Property:

• Appearance/Colour: off-white powder
• Vapor Pressure: 1.45E-07mmHg at 25°C
• Melting Point: 215 °C (dec.)(lit.)
• Refractive Index: -51.5 ° (C=4, 1mol/L HCl)
• Boiling Point: 413.1 °C at 760 mmHg
• PKA: 8.66(at 25℃)
• Flash Point: 207.9 °C
• PSA: 72.72000
• Density: 1.283 g/cm³
• LogP: 0.74150
• Storage Temp.: 2-8°C
• Sensitive.: Air & Light Sensitive
• Solubility.: Practically insoluble in water, in ethanol (96 per cent) and in methylene chloride. It dissolves in hydrochloric acid.
• Water Solubility.: <0.01 g/100 mL at 18℃
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 183.08954328
• Heavy Atom Count: 13
• Complexity: 154
• Transport DOT Label: Poison

Purity/Quality:

Epinephrine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 23/24/25-52/53-36/37/38-33
• Safety Statements: 36/37/39-45-61-26-23

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CNCC(C1=CC(=C(C=C1)O)O)O
• Isomeric SMILES: CNC[C@@H](C1=CC(=C(C=C1)O)O)O
• Recent ClinicalTrials: Lidocaine Irrigation in Shoulder Arthroscopy
• Recent EU Clinical Trials: Ultrasound-guided Genicular Nerve Block an Analgesic Alternative to LIA for
• Recent NIPH Clinical Trials: Anesthetic efficacy of anterior technique for pulpectomy of mandibular posterior teeth
• Description: The combination of the catechol nucleus, the β-hydroxyl group, and the N-methyl give EPI a direct action and a strong affinity for all adrenergic receptors. Epinephrine and all other catechols are chemically susceptible to oxygen and other oxidizing agents, especially in the presence of bases and light, quickly decomposing to inactive quinones. Therefore, all catechol drugs are stabilized with antioxidants and dispensed in air-tight amber containers.
• Uses: L-Adrenaline (Epinephrine) belongs to a group of the compounds known as catecholamines, which play an important role in the regulation of physiological process in living organisms. The antioxidant activity and antioxidant mechanism of L-adrenaline was cla Gibberellic Acid-3 (GA-3) is a plant growth regulator
• Indications: Epinephrine administered subcutaneously is used to manage severe acute episodes of bronchospasm and status asthmaticus. In addition to its bronchodilator activity through β-adrenoceptor stimulation, a portion of the therapeutic utility of epinephrine in these acute settings may be due to a reduction in pulmonary edema as a result of pulmonary vasoconstriction, the latter effect resulting from α-adrenoceptor stimulation.
• Therapeutic Function: Vasoconstrictor
• Biological Functions: Epinephrine is found only in very low concentrations in the mammalian CNS, and it is unlikely to play a major role as a neurotransmitter.
• Clinical Use: The ability of epinephrine to stimulate β2-receptors hasled to its use by injection and by inhalation to relaxbronchial smooth muscle in asthma and in anaphylacticreactions. Several OTC preparations (e.g., Primatene, Bronkaid)used for treating bronchial asthma use E. It is also usedin inhibiting uterine contraction. Because of its α-activity, Eis used to treat hypotensive crises and nasal congestion, toenhance the activity of local anesthetics, and as a constrictorin hemorrhage.In addition, E is used in the treatment of open-angle glaucoma,where it apparently reduces intraocular pressure byincreasing the rate of outflow of aqueous humor from theanterior chamber of the eye. The irritation often experiencedon instillation of E into the eye has led to the developmentof other preparations of the drug that potentially are not asirritating. One such example is dipivefrin. Epinephrine is used in a variety of clinical situations, and although concern has been expressed about the use of epinephrine in asthma, it is still used extensively for the management of acute attacks.
• Drug interactions: Potentially hazardous interactions with other drugs Alpha-blockers: avoid with tolazoline. Anaesthetics: increased risk of arrhythmias if given with volatile anaesthetics. Antidepressants: increased risk of arrhythmias and hypertension if given with tricyclics; MAOIs and moclobemide may cause hypertensive crisis. Beta-blockers: increased risk of severe hypertension and bradycardia. Clonidine: possible increased risk of hypertension. Dopaminergics: effects possibly increased by entacapone; avoid concomitant use with rasagiline. Guanethidine: increased risk of hypertension. Sympathomimetics: effects possibly enhanced by dopexamine.

Technology Process of Epinephrine

There total 32 articles about Epinephrine 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: 100.0%

(R)-4-(1-hydroxy-2-(methylamino)ethyl)benzen-1,2-diol L-tartrate (16536-89-3,8028-06-6) → L-epinephrine (51-43-4,51028-73-0)

Guidance literature:

With ammonium hydroxide; In water; at 5 - 10 ℃; for 0.5h; pH=8.5;

Reference yield: 97.0%

(R)-1-(3,4-Dimethoxy-phenyl)-2-methylamino-ethanol (41787-64-8) → L-epinephrine (51-43-4,51028-73-0)

Guidance literature:

With boron tribromide;

DOI:10.1016/S0040-4039(96)02515-4

Reference yield: 93.0%

epinephrine bitartrate (16536-89-3,8028-06-6) → L-epinephrine (51-43-4,51028-73-0)

Guidance literature:

With ammonium hydroxide; In water; at 5 - 15 ℃; for 3h; pH=9; Inert atmosphere; Darkness;

upstream raw materials:

R-(+)-2,2'-dinitrobiphenyl-6,6'-dicarbonsaeure-di-N,N'-1-(3,4-dihydroxyphenyl)-1-hydroxy-2-methylamido-ethan

(R)-1-(3,4-Dimethoxy-phenyl)-2-methylamino-ethanol

L-Tartaric acid

adrenalone

Downstream raw materials:

methylamine

(+/-)-epinine β-sulfonate < (+/-)-N-methyl-2-(3,4-dihydroxyphenyl)ethylammonium-2-sulfonate >

(R)-2-(acetyl-methyl-amino)-1-(3,4-dihydroxy-phenyl)-ethanol

C₁₂H₃₀N₆*C₉H₁₃NO₃*3H⁽¹⁺⁾

Refernces

• 1、 -. "PROCESS FOR THE SYNTHESIS OF OPTICALLY ACTIVE BETA-AMINO ALCOHOLS". Page/Page column 15. . Retrieved 2019/11/04.
• 2、 Hellinghausen, Garrett,Lopez, Diego A.,Lee, Jauh T.,Wang, Yadi,Weatherly, Choyce A.,Portillo, Abiud E.,Berthod, Alain,Armstrong, Daniel W.. "Evaluation of the Edman degradation product of vancomycin bonded to core-shell particles as a new HPLC chiral stationary phase". . p. 1067 - 1078. Retrieved 2018/08/01.