Adrenalone

Base Information

• Chemical Name: Adrenalone
• CAS No.: 99-45-6
• Molecular Formula: C9H11 N O3
• Molecular Weight: 181.191
• Hs Code.: 2922509090
• European Community (EC) Number: 202-756-9
• NSC Number: 243611
• UNII: EGU41QL329
• DSSTox Substance ID: DTXSID5048710
• Nikkaji Number: J4.970K
• Wikipedia: Adrenalone
• Wikidata: Q2186476
• NCI Thesaurus Code: C81339
• Metabolomics Workbench ID: 154205
• ChEMBL ID: CHEMBL2103996
• Mol file: 99-45-6.mol

Synonyms:adrenalone;adrenalone hydrochloride;Stryphnasal

Chemical Property of Adrenalone

Chemical Property:

• Melting Point: 235.5°C (rough estimate)
• Refractive Index: 1.5270 (estimate)
• Boiling Point: 405.6°Cat760mmHg
• PKA: 7.32±0.20(Predicted)
• Flash Point: 199.1°C
• PSA: 69.56000
• Density: 1.265g/cm³
• LogP: 0.89080
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Aqueous Acid (Slightly)
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 181.07389321
• Heavy Atom Count: 13
• Complexity: 184

Purity/Quality:

98%,99%, ^*data from raw suppliers

Adrenalone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNCC(=O)C1=CC(=C(C=C1)O)O
• Recent EU Clinical Trials: A DOUBLE BLIND PLACEBO CONTROLLED TRIAL OF TERLIPRESSIN IN THE MANAGEMENT OF SEVERE ALCOHOLIC HEPATITIS – A PRELIMINARY STUDY
• Uses: Adrenalone is a ketone derivative of Epinephrine (E588585) and a potential dopamine β oxidase inhibitor.
• Therapeutic Function: Hemostatic, Sympathomimetic, Vasoconstrictor

Technology Process of Adrenalone

There total 15 articles about Adrenalone 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%

tert-butyl (2-(3,4-bis((tert-butyldimethylsilyl)oxy)phenyl)-2-oxoethyl)(methyl)carbamate → adrenalone (99-45-6)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/acs.joc.9b02073

Reference yield: 70.0%

aq methylamine + hydrochloride salt of adrenalone + 2-chloro-3',4'-dihydroxyacetophenone (99-40-1) → adrenalone (99-45-6)

Guidance literature:

In ethanol;

Reference yield:

2-chloro-3',4'-dihydroxyacetophenone (99-40-1) + methylamine (74-89-5) → adrenalone (99-45-6)

Guidance literature:

upstream raw materials:

3,4-Dimethoxy-ω-methylaminoacetophenon

N-(3,4-dimethoxy-phenacyl)-N-methyl-toluene-4-sulfonamide

2-chloro-3',4'-dihydroxyacetophenone

methylamine

Downstream raw materials:

4-(3,4-dihydroxy-phenyl)-1-methyl-1,3-dihydro-imidazol-2-one

Epinephrine

(S)-4-[1-hydroxy-2-(methylamino)ethyl]pyrocatechol

N-(2-(3,4-dihydroxyphenyl)-2-oxoethyl)-N-methylacetamide

Refernces

• 1、 -. "Preparation method of adrenalone hydrochloride". Paragraph 0014; 0033; 0038; 0043; 0046; 0047; 0058-0053. . Retrieved 2017/07/21.
• 2、 -. "Selective hydrogenolysis process". . . Retrieved 2008/06/13.