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MedKoo Cat#: 318196 | Name: Metaxalone
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Metaxalone is a muscle relaxant used to relax muscles and relieve pain caused by strains, sprains, and other musculoskeletal conditions. It is considered to be a moderately strong muscle relaxant, with relatively low incidence of side effects. Metaxalone appears to interact with the cytochrome p450 system and may act as a general central nervous system depressant.

Chemical Structure

Metaxalone
CAS#1665-48-1

Theoretical Analysis

MedKoo Cat#: 318196

Name: Metaxalone

CAS#: 1665-48-1

Chemical Formula: C12H15NO3

Exact Mass: 221.1052

Molecular Weight: 221.26

Elemental Analysis: C, 65.14; H, 6.83; N, 6.33; O, 21.69

Price and Availability

Size Price Availability Quantity
1g USD 250.00 2 weeks
2g USD 350.00 2 weeks
5g USD 650.00 2 weeks
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Related CAS #
No Data
Synonym
Metaxalone; Skelaxin; Methaxalonum; Metaxalon; Zorane; AHR 438; 3B2-1432; I06-0370;
IUPAC/Chemical Name
5-[(3,5-dimethylphenoxy)methyl]-1,3-oxazolidin-2-one
InChi Key
IMWZZHHPURKASS-UHFFFAOYSA-N
InChi Code
InChI=1S/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)
SMILES Code
CC1=CC(=CC(=C1)OCC2CNC(=O)O2)C
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Metaxalone (AHR438;NSC170959) is a muscle relaxant used to relax muscles.
In vitro activity:
The aim of this study was to investigate whether metaxalone might exert antioxidant and anti-inflammatory effects in HMC3 microglial cells. Control cells and IL-1β-stimulated cells were subsequently treated with metaxalone (10, 20, and 40 µM) for six hours. Metaxalone decreased MAO-A activity and expression, reduced NF-kB, TNF-α, and IL-6, enhanced IL-13, and also increased PPARγ, PGC-1α, and Nrf2 expression. Reference: Int J Mol Sci. 2021 Aug 5;22(16):8425. https://pubmed.ncbi.nlm.nih.gov/34445126/
In vivo activity:
Mouse macrophage RAW264.7 cells were cultured in Dulbecco's Modification of Eagle's Medium containing 10% fetal bovine serum in the presence of metaxalone. Metaxalone (1-100 μM) was found to decrease the number of macrophages by inhibiting the proliferation and stimulating the death of RAW264.7 cells in vitro. Furthermore, levels of caspase-3 were increased by metaxalone or β-caryophyllene and enhanced by their combination. Reference: Curr Mol Med. 2020;20(8):643-652. https://pubmed.ncbi.nlm.nih.gov/32065089/
Solvent mg/mL mM comments
Solubility
DMF 30.0 135.59
DMF:PBS (pH 7.2) (1:1) 0.5 2.26
DMSO 54.7 247.07
Ethanol 27.0 122.03
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 221.26 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Pallio G, D'Ascola A, Cardia L, Mannino F, Bitto A, Minutoli L, Picciolo G, Squadrito V, Irrera N, Squadrito F, Altavilla D. MAO-A Inhibition by Metaxalone Reverts IL-1β-Induced Inflammatory Phenotype in Microglial Cells. Int J Mol Sci. 2021 Aug 5;22(16):8425. doi: 10.3390/ijms22168425. PMID: 34445126; PMCID: PMC8395141. 2. Yamaguchi M, Levy RM. Metaxalone Suppresses Production of Inflammatory Cytokines Associated with Painful Conditions in Mouse Macrophages RAW264.7 Cells in Vitro: Synergistic Effect with β-caryophyllene. Curr Mol Med. 2020;20(8):643-652. doi: 10.2174/1566524020666200217102508. PMID: 32065089.
In vitro protocol:
Pallio G, D'Ascola A, Cardia L, Mannino F, Bitto A, Minutoli L, Picciolo G, Squadrito V, Irrera N, Squadrito F, Altavilla D. MAO-A Inhibition by Metaxalone Reverts IL-1β-Induced Inflammatory Phenotype in Microglial Cells. Int J Mol Sci. 2021 Aug 5;22(16):8425. doi: 10.3390/ijms22168425. PMID: 34445126; PMCID: PMC8395141.
In vivo protocol:
Yamaguchi M, Levy RM. Metaxalone Suppresses Production of Inflammatory Cytokines Associated with Painful Conditions in Mouse Macrophages RAW264.7 Cells in Vitro: Synergistic Effect with β-caryophyllene. Curr Mol Med. 2020;20(8):643-652. doi: 10.2174/1566524020666200217102508. PMID: 32065089.
1: Surmaitis RM, Nappe TM, Cook MD. Serotonin syndrome associated with therapeutic metaxalone in a patient with cirrhosis. Am J Emerg Med. 2016 Feb;34(2):346.e5-6. doi: 10.1016/j.ajem.2015.06.043. Epub 2015 Jun 19. PubMed PMID: 26159819. 2: Bishop-Freeman SC, Miller A, Hensel EM, Winecker RE. Postmortem Metaxalone (Skelaxin®) Data from North Carolina. J Anal Toxicol. 2015 Oct;39(8):629-36. doi: 10.1093/jat/bkv066. PubMed PMID: 26378137. 3: Curtis B, Jenkins C, Wiens AL. A rare fatality attributed solely to metaxalone. J Anal Toxicol. 2015 May;39(4):321-3. doi: 10.1093/jat/bkv008. Epub 2015 Feb 10. PubMed PMID: 25673649. 4: Martini DI, Nacca N, Haswell D, Cobb T, Hodgman M. Serotonin syndrome following metaxalone overdose and therapeutic use of a selective serotonin reuptake inhibitor. Clin Toxicol (Phila). 2015 Mar;53(3):185-7. doi: 10.3109/15563650.2015.1009993. Epub 2015 Feb 11. PubMed PMID: 25671244. 5: Bosak AR, Skolnik AB. Serotonin syndrome associated with metaxalone overdose. J Med Toxicol. 2014 Dec;10(4):402-5. doi: 10.1007/s13181-014-0404-5. PubMed PMID: 24805103; PubMed Central PMCID: PMC4252289. 6: Rao RN, Farah H, Sahu PK, Janarthan M, Naidu ChG. Development and validation of a stability-indicating assay including the isolation and characterization of degradation products of metaxalone by LC-MS. Biomed Chromatogr. 2013 Dec;27(12):1733-40. doi: 10.1002/bmc.2987. Epub 2013 Jul 23. PubMed PMID: 23881540. 7: Goswami D, Saha A, Gurule S, Khuroo A, Monif T, Vats P. Metaxalone estimation in biological matrix using high-throughput LC-MS/MS bioanalytical method. J Chromatogr B Analyt Technol Biomed Life Sci. 2012 Aug 1;902:132-6. doi: 10.1016/j.jchromb.2012.05.034. Epub 2012 Jun 4. PubMed PMID: 22766230. 8: Trivedi RK, Patel MC. Development of a Stability-Indicating RP-UPLC Method for Rapid Determination of Metaxalone and its Degradation Products in Solid Oral Dosage Form. Sci Pharm. 2012 Jun;80(2):353-66. doi: 10.3797/scipharm.1112-08. Epub 2012 Feb 21. PubMed PMID: 22896822; PubMed Central PMCID: PMC3383218. 9: Panda SS, Patanaik D, Ravi Kumar BV. New Stability-Indicating RP-HPLC Method for Determination of Diclofenac Potassium and Metaxalone from their Combined Dosage Form. Sci Pharm. 2012;80(1):127-37. doi: 10.3797/scipharm.1109-16. Epub 2011 Dec 5. PubMed PMID: 22396909; PubMed Central PMCID: PMC3293350. 10: Forrester MB. Pediatric metaxalone ingestions reported to Texas poison control centers, 2000-2007. Pediatr Emerg Care. 2010 Jan;26(1):15-8. doi: 10.1097/PEC.0b013e3181c330dc. PubMed PMID: 20042913. 11: Forrester MB. Adult metaxalone ingestions reported to Texas poison control centers, 2000-2006. Hum Exp Toxicol. 2010 Jan;29(1):55-62. doi: 10.1177/0960327108098150. Epub 2009 Nov 19. PubMed PMID: 19933254. 12: Zhang J, Fan X, Liu Y, Bo L, Liu X. Synthesis of poly(ethylene glycol)-metaxalone conjugates and study of its controlled release in vitro. Int J Pharm. 2007 Mar 6;332(1-2):125-31. Epub 2006 Sep 29. PubMed PMID: 17067768. 13: Nirogi RV, Kandikere VN, Shukla M, Mudigonda K, Shrivastava W, Datla PV. Quantification of metaxalone in human plasma by liquid chromatography coupled to tandem mass spectrometry. J Anal Toxicol. 2006 May;30(4):245-51. PubMed PMID: 16803662. 14: Poklis JL, Ropero-Miller JD, Garside D, Winecker RE. Metaxalone (Skelaxin)-related death. J Anal Toxicol. 2004 Sep;28(6):537-41. PubMed PMID: 15516312. 15: KLEBER JW, NASH JF, LEE CC. QUALITATIVE AND QUANTITATIVE TESTS FOR METAXALONE. J Pharm Sci. 1964 Dec;53:1522-3. PubMed PMID: 14255136. 16: FATHIE K. A SECOND LOOK AT A SKELETAL MUSCLE RELAXANT: A DOUBLE-BLIND STUDY OF METAXALONE. Curr Ther Res Clin Exp. 1964 Nov;6:677-83. PubMed PMID: 14240758. 17: BROWN WE. EVALUATION OF METAXALONE (SKELAXIN). JAMA. 1964 Jan 25;187:291-2. PubMed PMID: 14074467. 18: Moore KA, Levine B, Fowler D. A fatality involving metaxalone. Forensic Sci Int. 2005 May 10;149(2-3):249-51. PubMed PMID: 15749367. 19: Toth PP, Urtis J. Commonly used muscle relaxant therapies for acute low back pain: a review of carisoprodol, cyclobenzaprine hydrochloride, and metaxalone. Clin Ther. 2004 Sep;26(9):1355-67. Review. PubMed PMID: 15530999. 20: Kuykendall JR, Rhodes RS. Auditory hallucinations elicited by combined meclizine and metaxalone use at bedtime. Ann Pharmacother. 2004 Nov;38(11):1968-9. Epub 2004 Sep 28. PubMed PMID: 15454584.

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