Metaxalone | CAS#1665-48-1

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

MedKoo CAT#: 318196

CAS#: 1665-48-1

Description: 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

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 318196
Name: Metaxalone
CAS#: 1665-48-1
Chemical Formula: C12H15NO3
Exact Mass: 221.11
Molecular Weight: 221.256
Elemental Analysis: C, 65.14; H, 6.83; N, 6.33; O, 21.69

Price and Availability

Size	Price	Availability
1g	USD 250	2 weeks
2g	USD 350	2 weeks
5g	USD 650	2 weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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

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Product Data:

Product Data

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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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
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

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.

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.

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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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