1665-48-1 Usage
Description
Metaxalone is a white crystalline solid that functions as a muscle relaxant. It is used to relax muscles and relieve pain, particularly in the context of musculoskeletal conditions. The exact molecular or cellular actions of metaxalone are not fully known, but its efficacy in reducing muscle spasm, limitations in normal motion, and pain is well-documented.
Uses
Used in Pharmaceutical Industry:
Metaxalone is used as a skeletal muscle relaxant for the treatment of painful peripheral musculoskeletal conditions and spasticity from upper motor neuron syndromes. It helps in reducing muscle spasm, limitations in normal motion, and pain associated with these conditions.
Used in Pain Management:
Metaxalone is used as an adjunct therapy in combination with analgesics to address low back pain and other musculoskeletal pain issues. Its muscle-relaxing properties complement the pain-relieving effects of analgesics, providing a more comprehensive approach to pain management.
While the provided materials do not specify other industries where Metaxalone might be used, its primary application is within the pharmaceutical industry for the treatment of musculoskeletal conditions and pain management.
Originator
Skelaxin,Robins,US,1962
Manufacturing Process
Urea (118 g, 1.96 mols) was added to 192 g (0.98 mol) of 3-(3',5'- dimethylphenoxy)-1,2-propane-diol which had previously been heated to 150°C. The reaction mixture was then heated rapidly to 195° to 200°C and maintained at this temperature for 5 hours with constant stirring. The resulting mixture was partitioned between water and ethyl acetate and the ethyl acetate layer was dried over sodium sulfate and concentrated. The residue was distilled in vacuo and the fraction boiling at 220° to 225°C/1.5 mm was collected. Yield, 172 g (79%). The distillate was crystallized from dry ethyl acetate; MP, 121.5° to 123°C.
Therapeutic Function
Muscle relaxant
Check Digit Verification of cas no
The CAS Registry Mumber 1665-48-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,6,6 and 5 respectively; the second part has 2 digits, 4 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 1665-48:
(6*1)+(5*6)+(4*6)+(3*5)+(2*4)+(1*8)=91
91 % 10 = 1
So 1665-48-1 is a valid CAS Registry Number.
InChI:InChI=1/C12H15NO3/c1-8-3-9(2)5-10(4-8)15-7-11-6-13-12(14)16-11/h3-5,11H,6-7H2,1-2H3,(H,13,14)
1665-48-1Relevant articles and documents
Solid Phase Behavior, Polymorphism, and Crystal Structure Features of Chiral Drug Metaxalone
Bredikhin, Alexander A.,Zakharychev, Dmitry V.,Gubaidullin, Aidar T.,Bredikhina, Zemfira A.
, p. 6627 - 6639 (2018/11/21)
In addition to the previously known A-rac and B-rac polymorphs of the chiral drug metaxalone 1, an enantiopure A-(S)-form was obtained and studied. According to X-ray analysis, the crystalline organization of this form is close to the A-rac-1 polymorph. Crystallization of metaxalone melts is accompanied by the formation of a previously unknown metastable C-phase, which in the case of both racemic and enantiomeric samples are transformed into A-rac-1 or A-(S)-1. Analysis of the PXRD and IR spectra of crystalline samples revealed a similarity of the internal structure for the A-(S)-1, A-rac-1, C-(S)-1, and C-rac-1 crystalline forms and the essential difference of all of these phases from the B-rac-1 phase. According to the thermochemical data, the dependences of the change in the Gibbs free energy for all the phases studied are plotted in the interval from the melting point to 20 °C. Under standard conditions, the crystalline modifications of metaxalone, relative to δG0, form such a series: B-rac-1 A-(S)-1 ≈ A-rac-1 C-rac-1 C-(S)-1. A model that describes all the experimentally revealed features of metaxalone crystallization is proposed.
PROCESS FOR PREPARATION OF METAXALONE
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Page/Page column 2, (2012/01/03)
An improved process for the preparation of Metaxalone of formula I wherein, reacting 3,5-dimethyl phenol with 3-chloro-1,2-propane diol in presence of a base, to produce 3-(3,5-dimethylphenoxy)propane-1,2-diol which is further reacted with urea in presence of polyalkylene glycol to obtain Metaxalone, which is optionally crystallized in ethyl acetate in presence of mineral acid.
METAXALONE SYNTHESIS
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Page/Page column 2-4, (2008/06/13)
A process for preparing metaxalone comprising reacting 3-(3,5-dimethylphenoxy)-1-amino-2-propanol with methyl carbamate in the presence of a strong base to obtain metaxalone.