Andarine

Base Information

• Chemical Name: Andarine
• CAS No.: 401900-40-1
• Molecular Formula: C₁₉H₁₈F₃N₃O₆
• Molecular Weight: 441.364
• European Community (EC) Number: 803-892-7
• UNII: 7UT2HAH49H
• DSSTox Substance ID: DTXSID40193187
• Nikkaji Number: J2.012.585C
• Wikipedia: Andarine
• Wikidata: Q4753617
• Pharos Ligand ID: 3LZ9JUR2RU1N
• Metabolomics Workbench ID: 150599
• ChEMBL ID: CHEMBL125236
• Mol file: 401900-40-1.mol

Synonyms:3-(4-acetylamino-phenoxy)-2-hydroxy-2-methyl-N-(4-nitro-3-trifluoromethylphenyl)propionamide;3-(4-acetylaminophenoxy)-2-hydroxy-2-methyl-N-(4-nitro-3-trifluoromethylphenyl)-propionamide;andarine;S-4 cpd

Chemical Property of Andarine

Chemical Property:

• Appearance/Colour: Pale yellow solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 70-74 °C
• Refractive Index: 1.605
• Boiling Point: 698.735 °C at 760 mmHg
• PKA: 12.13±0.29(Predicted)
• Flash Point: 376.381 °C
• PSA: 133.48000
• Density: 1.472 g/cm³
• LogP: 4.00970
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: 1.2 mg/mL in water
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 441.11476979
• Heavy Atom Count: 31
• Complexity: 663

Purity/Quality:

99% ^*data from raw suppliers

Andarine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): 9666695
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1=CC=C(C=C1)OCC(C)(C(=O)NC2=CC(=C(C=C2)[N+](=O)[O-])C(F)(F)F)O
• Isomeric SMILES: CC(=O)NC1=CC=C(C=C1)OC[C@@](C)(C(=O)NC2=CC(=C(C=C2)[N+](=O)[O-])C(F)(F)F)O
• Description: Andarine (S-4) is the arylpropionamide-derived compound [S-3-(4-acetylamino-phenoxy)-2-hydroxy-2-methyl-N-(4-nitro-3-trifluoromethyl-phenyl)-propionamide] first described by Yin et al. to be a selective androgen receptor modulator (SARM). Andarine (S-4) was shown by in vitro and in vivo studies to be an effective anabolic agonist, without side-effects often associated with anabolic-androgenic steroids, relating principally to substrate affinity for 5α-reductase to produce DHT in the prostate. Unfortunately the benefits that SARMs such as andarine (S-4) may provide to clinical medicine have the potential for misuse in sports where athletes and/or their handlers may seek to gain unfair advantage with the assumption that these compounds are undetectable by anti-doping laboratories. SARMs are therefore prohibited for use by the International Federation of Horseracing Authorities and the World Anti-Doping Agency (WADA).
• Uses: It is a potent and tissue-selective androgen receptor modulator (SARM)

Technology Process of Andarine

There total 6 articles about Andarine 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: 86.0%

4-acetaminophenol (103-90-2,8055-08-1) + N-[4-nitro-3-(trifluoromethyl)phenyl]-(2R)-3-bromo-2-hydroxy-2-methylpropanamide (206193-18-2) → Ostarine (885324-25-4,401900-40-1)

Guidance literature:

With potassium carbonate; benzyltri(n-butyl)ammonium chloride; In butanone; Heating / reflux;

Reference yield: 79.3%

4-acetaminophenol (103-90-2,8055-08-1) + (S)-(-)-3-bromo-2-hydroxy-2-methyl-N-[(4-nitro-3-trifluoromethyl)phenyl]propanamide (216665-24-6) → (2R)-3-(4-acetamidophenoxy)-N-[(4-nitro-3-(trifluoromethyl)phenyl)]-2-hydroxy-2-methylpropanamide (885324-25-4,401900-40-1)

Guidance literature:

With benzyltri(n-butyl)ammonium chloride; potassium carbonate; In isopropyl alcohol; for 4h; Inert atmosphere; Reflux;

Reference yield:

N-[4-nitro-3-(trifluoromethyl)phenyl]-(2R)-3-bromo-2-hydroxy-2-methylpropanamide (206193-18-2) → Ostarine (885324-25-4,401900-40-1)

Guidance literature:

Multi-step reaction with 2 steps

1: K₂CO₃ / acetone / Heating

2: K₂CO₃ / propan-2-ol / Heating

With potassium carbonate; In isopropyl alcohol; acetone;

DOI:10.1021/jm030336u

upstream raw materials:

4-acetaminophenol

(S)-N-(4-nitro-3-(trifluoromethyl)phenyl)-2-methyloxirane-2-carboxamide

N-[4-nitro-3-(trifluoromethyl)phenyl]-(2R)-3-bromo-2-hydroxy-2-methylpropanamide

4-nitro-3-(trifluoromethyl)benzeneamine

Refernces

• 1、 -. "METHODS OF TREATING UROLOGICAL DISORDERS USING SARMs". Paragraph 0424-0425. . Retrieved 2016/05/10.
• 2、 -. "Compositions comprising 5-alpha reductase inhibitors, and SARMs and methods of use thereof". Page/Page column 23. . Retrieved 2010/11/24.