Introduction：Basic information about Afloqualone CAS 56287-74-2, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Afloqualone Basic information
| Product Name: | Afloqualone |
| Synonyms: | Afloqualone 6-Amino-2-(fluoromethyl)-3-(2-methylphenyl)-quinazolin-4-one;6-Amino-2-fluoromethyl-3-(o-tolyl)-quinazolin-4(3H)-one;H-495;HQ 495;HQ-495;Afloquanone;6-aMino-2-fluoroMethyl-3-(o-tolyl)-4(3h)-quinaz...;6-amino-2-(fluoromethyl)-3-(2-methylphenyl)-4(3h)-quinazolinon |
| CAS: | 56287-74-2 |
| MF: | C16H14FN3O |
| MW: | 283.3 |
| EINECS: | 1592732-453-0 |
| Product Categories: | API;Other APIs |
| Mol File: | 56287-74-2.mol |
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Afloqualone Chemical Properties
| Melting point | 195-196°C |
| Boiling point | 492.5±55.0 °C(Predicted) |
| density | 1.2529 (estimate) |
| storage temp. | under inert gas (nitrogen or Argon) at 2–8 °C |
| solubility | DMSO (Slightly), Methanol (Slightly) |
| form | Solid |
| pka | 2.73±0.70(Predicted) |
| color | White to Off-White |
| InChI | InChI=1S/C16H14FN3O/c1-10-4-2-3-5-14(10)20-15(9-17)19-13-7-6-11(18)8-12(13)16(20)21/h2-8H,9,18H2,1H3 |
| InChIKey | VDOSWXIDETXFET-UHFFFAOYSA-N |
| SMILES | N1C2=C(C=C(N)C=C2)C(=O)N(C2=CC=CC=C2C)C=1CF |
| CAS DataBase Reference | 56287-74-2(CAS DataBase Reference) |
Safety Information
| Toxicity | LD50 in mice (mg/kg): 315.1 i.p. (Tani) |
Afloqualone Usage And Synthesis
| Description | Afloqualone is a centrally acting muscle relaxant useful in the management ofvarious spastic conditions, including cerebral palsy, cervical spondylosis, andmultiple sclerosis. It is closely related to the hypnotidsedative methaqualone. |
| Description | Afloqualone (Item No. 21834) is an analytical reference standard categorized as a quinazolinone. This product is intended for research and forensic applications. |
| Originator | Tanabe (Japan) |
| Uses | Afloqualone acts as a muscle relaxant in humans and may be used in the treatment of muscle spasms affecting rheumatoid arthritis. |
| Definition | ChEBI: Afloqualone is an organic molecular entity. |
| Manufacturing Process | 14.4 g (0.053 mol) of N-(2-amino-5-nitrobenzoyl)-o-toluidine and 6.3 g (0.08mol) of pyridine are dissolved in 300 ml of tetrahydrofuran. 12.2 g (0.126mol) of fluoroacetyl chloride are added to the solution for 10 minutes underice-cooling. The solution is stirred at the same temperature for 30 minutesand then at room temperature for 2.5 hours. The reaction solution is allowedto stand at room temperature overnight. The crystalline precipitate is collectedby filtration, washed with water and then dried. 16.4 g of N-(2-fluoroacetamido-5-nitrobenzoyl)-o-toluidine are obtained. Yield: 93.7%; MP238-239°C.
16.5 g (0.05 mol) of N-(2-fluoroacetamido-5-nitrobenzoyl)-o-toluidine and25.5 g (0.25 mol) of acetic acid anhydride are dissolved in 250 ml of glacialacetic acid. The solution is refluxed for 2 hours under heating. Then, thereaction solution is evaporated to remove solvent. The residue thus obtainedis poured into ice-water, and the aqueous mixture is adjusted to pH 9 withpotassium carbonate. The crystalline precipitate is collected by filtration. 15.5g of 2-fluoromethyl-3-(o-tolyl)-6-nitro-4(3H)-quinazolinone are obtained.Yield: 98.7%; MP 155-158°C (recrystallized from ethanol).
A mixture of 2.0 g (0.064 mol) of 2-fluoromethyl-3-(o-tolyl)-6-nitro-4(3H)-quinazolinone, 0.2 g of 5% palladium-carbon and 100 ml of acetic acid isshaken for 30 minutes in hydrogen gas. The initial pressure of hydrogen gas isadjusted to 46 lb and the mixture is heated with an infrared lamp during thereaction. After 30 minutes of this reaction, the pressure of hydrogen gasdecreases to 6 lb. After the mixture is cooled, the mixture is filtered toremove the catalyst. The filtrate is evaporated to remove acetic acid, and theresidue is dissolved in chloroform. The chloroform solution is washed with 5%aqueous sodium hydroxide and water, successively. Then, the solution is driedand evaporated to remove solvent. The oily residue thus obtained is dissolvedin 2 ml of chloroform, and the chloroform solution is passed through a columnof 200 g of silica gel. The silica gel column is eluted with ethyl acetatebenzene(1:1). Then, the eluate is evaporated to remove solvent. The crudecrystal obtained is washed with isopropyl ether and recrystallized from isopropanol. 0.95 g of 2-fluoromethyl-3-(o-tolyl)-6-amino-4(3H)-quinazolinoneis obtained. Yield: 52.5%; MP 195-196°C. |
| Brand name | AROFUTO |
| Therapeutic Function | Muscle relaxant |
| References | [1] T OCHIAI R I. Pharmacological studies on 6-amino-2-fluoromethyl-3-(O-tolyl)-4(3H)-quinazolinone (afloqualone), a new centrally acting muscle relaxant. (II) Effects on the spinal reflex potential and the rigidity.[J]. Japanese journal of pharmacology, 1982: 427-438. DOI: 10.1254/jjp.32.427 |
Afloqualone Preparation Products And Raw materials
| Raw materials | FLUOROACETYL CHLORIDE-->Hydrogen-->Acetic anhydride |
