m-Xylene (CED0000041)

Record Information

Version

1.0

Creation Date

2009-03-06 18:58:00 UTC

Update Date

2026-08-24 10:24:06 UTC

Accession Number

CHEM000054

Identification

Common Name

m-Xylene

Class

Small Molecule

Description

m-Xylene belongs to the xylenes, a subclass of benzene and substituted derivatives within the organic compounds. This exogenous benzenoid has the formula C8H10 and an average molecular weight of 106.17 g/mol. At room temperature, it exists as a liquid. Exposure to the compound occurs through inhalation, oral, and touch routes. It is released from 44 recorded sources, including drinking water, coins, and various household cleaning and consumer products such as soap detergents, bleaching agents, and perfumes within detergents and soaps. It is also found in food processing and cookware, including food contact materials and fermentation processes for beer, as well as building and construction materials like roofs, fencing, and sunshades. Additionally, it is released from electrical and electronic equipment, including antennas, amplifiers, and adjustable resistors. Regarding materials, m-Xylene is used in polyurethane, polyamide, and acrylonitrile butadiene styrene. It is present in polyethylene terephthalate and released in polycarbonate, polystyrene, and polyvinyl chloride. Its status is inconclusive in styrene acrylonitrile, superabsorbent polymer, ethylene vinyl alcohol, high-density polyethylene, and low-density polyethylene. The compound interacts with five recorded protein targets: acetylcholinesterase (ACHE), estrogen receptor (ESR1), transient receptor potential cation channel subfamily A member 1 (TRPA1), cytochrome P450 4B1 (CYP4B1), and cytochrome P450 2E1 (CYP2E1). Certain metabolites of xylene have been shown to inhibit pulmonary mixed-function oxidases.

Contaminant Type

Aromatic Hydrocarbon
Food Toxin
Industrial/Workplace Toxin
Lachrymator
Metabolite
Natural Compound
Organic Compound
Pollutant
Solvent

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,3-Dimethylbenzene	ChEBI
1,3-Dimethylbenzol	ChEBI
1,3-Xylene	ChEBI
3-Xylene	ChEBI
m-Dimethylbenzene	ChEBI
m-Methyltoluene	ChEBI
m-Xylol	ChEBI
Meta-xylene	ChEBI

Chemical Formula

C₈H₁₀

Average Molecular Mass

106.165 g/mol

Monoisotopic Mass

106.078 g/mol

CAS Registry Number

108-38-3

IUPAC Name

1,3-xylene

Traditional Name

M-xylene

SMILES

CC1=CC(C)=CC=C1

InChI Identifier

InChI=1S/C8H10/c1-7-4-3-5-8(2)6-7/h3-6H,1-2H3

InChI Key

IVSZLXZYQVIEFR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as m-xylenes. These are aromatic compounds that contain a m-xylene moiety, which is a monocyclic benzene carrying exactly two methyl groups at the 1- and 3-positions.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Xylenes

Direct Parent

m-Xylenes

Alternative Parents

Substituents

M-xylene
Aromatic hydrocarbon
Unsaturated hydrocarbon
Hydrocarbon
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

xylene (CHEBI:28488 )
an aromatic compound (META-XYLENE )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Liquid

Appearance

Colorless liquid.

Experimental Properties

Property	Value
Melting Point	-47.8 °C
Boiling Point	138.5 °C
Solubility	0.106 mg/mL at 25 °C [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; 0.161 mg/mL at 25°C [SANEMASA,I et al. (1982)]

Predicted Properties

Property	Value	Source
Water Solubility	0.2 g/L	ALOGPS
logP	3.15	ALOGPS
logP	3	ChemAxon
logS	-2.7	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	36.14 m³·mol⁻¹	ChemAxon
Polarizability	13.09 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum	splash10-052f-9400000000-2f01cb2d1d9a3cb2c00a	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-052f-9400000000-df0f65246037f2bfb507	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-0a4i-0900000000-2370bbe07a9d5e20584f	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-052f-9400000000-2f01cb2d1d9a3cb2c00a	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-052f-9400000000-df0f65246037f2bfb507	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-0a4i-0900000000-2370bbe07a9d5e20584f	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0a4i-5900000000-8bb4470d1d34c4bdbba9	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0900000000-1408ea7794c1dd42097e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0900000000-a18170561f3e5d8b9f5b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0aor-9500000000-7f307619895b31097120	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0900000000-51ad3e28bd0c6572b441	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0900000000-51ad3e28bd0c6572b441	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-4900000000-1f1973b947c3c42a28b6	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-2900000000-b1f1a68d446da42d7ad6	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004l-9100000000-fc29268619d061ae3611	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-9000000000-da7286fba0f1ecc72e96	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0900000000-861947f0491f909a2588	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0900000000-861947f0491f909a2588	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-1900000000-d421ee990836412c0901	Not Available	View Spectrum
MS	MS Spectrum	splash10-052f-9300000000-1d9e623f1ed39f29c5b6	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

m-Xylene is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.

Carcinogenicity (IARC Classification)

3, not classifiable as to its carcinogenicity to humans. (4)

Minimum Risk Level

Acute Inhalation: 2 ppm (3) Intermediate Inhalation: 0.6 ppm (3) Chronic Inhalation: 0.05 ppm (3) Acute Oral: 1 mg/kg/day (3) Intermediate Oral: 0.4 mg/kg/day (3) Chronic Oral: 0.2 mg/kg/day (3)

Symptoms

Dizziness, drowsiness, headache, and nausea can follow ihnalation and ingestion exposure. Burning sensations and abdominal pain can also result from ingestion. Dry skin, redness, and pain can result from dermal and eye exposure depending on the route of exposure. Conjunctivitis, dermatitis, irritation to respiratory tract, dyspnea, anorexia, vomiting, fatigue, vertigo, incoordination, irritation, gangrene and anemia can also follow xylene poisoning. (1)

Treatment

If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
1590.0	mg/kg	Not Available	Rat	LD50	Oral	experimental	T18
6350.0	ppm	Not Available	Rat	LC50	Inhalation (4 hours)	experimental	T21
1548.0	mg/kg	Not Available	Mouse	LD50	Intraperitoneal	experimental	T26
1700.0	mg/kg	Not Available	Rat	LD50	Subcutaneous	experimental	T26
6661.0	mg/kg/day	Not Available	Rat	LD50	Oral	experimental	L165
3228.0	mg/kg/day	Not Available	Rabbit	LD50	Dermal	experimental	L165

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
10	Insecticides	Agriculture & land management	Not Available
115	Drinking water	Drinking water & water supply	Not Available
233	Brushes	Personal care & cosmetics	Not Available
490		Personal care & cosmetics	Not Available
494	Food contact materials	Food, food processing & cookware	Not Available
496	Fencing	Building & Construction	Not Available
499	Roofs	Building & Construction	Not Available
500	Stairs And Ramps	Building & Construction	Not Available
501	Sunshades Awnings Or Outside Screens	Building & Construction	Not Available
502	Sunshades Awnings Or Outside Screens	Building & Construction	Not Available
504	Adjustable Resistors	Electrical & Electronic Equipment	Not Available
505	Amplifiers	Electrical & Electronic Equipment	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
507	Auxiliary Devices	Electrical & Electronic Equipment	Not Available
508	Coils	Electrical & Electronic Equipment	Not Available
510	Communication Cables Or Conductors	Electrical & Electronic Equipment	Not Available
511	Conductors Or Conductive Bodies Characterised By The Conductive Materials	Electrical & Electronic Equipment	Not Available
513	Cores Yokes Or Armatures	Electrical & Electronic Equipment	Not Available
514	Discharge Lamps	Electrical & Electronic Equipment	Not Available
517	Electric Switches	Electrical & Electronic Equipment	Not Available
518	Electrically Stimulated Smoking Devices	Electrical & Electronic Equipment	Not Available
519	Electrodes	Electrical & Electronic Equipment	Not Available
520	Emergency Protective Devices	Electrical & Electronic Equipment	Not Available
521	Fixed Capacitors And Their Manufacture	Electrical & Electronic Equipment	Not Available
523	Gas Filled Discharge Tubes With Solid Cathode	Electrical & Electronic Equipment	Not Available
524	Hybrid Capacitors	Electrical & Electronic Equipment	Not Available
525	Line Transmission Systems	Electrical & Electronic Equipment	Not Available
526	Loudspeakers	Electrical & Electronic Equipment	Not Available
527	Magnets	Electrical & Electronic Equipment	Not Available
529	Power Cables	Electrical & Electronic Equipment	Not Available
530	Radio Transmission Systems	Electrical & Electronic Equipment	Not Available
532	Selectors	Electrical & Electronic Equipment	Not Available
537	Television Systems	Electrical & Electronic Equipment	Not Available
538	Thin Magnetic Films	Electrical & Electronic Equipment	Not Available
544	Fermentation Processes For Beer	Food, food processing & cookware	Not Available
545	Food Preservation	Food, food processing & cookware	Not Available
549	Preparation Of Wine Or Sparkling Wine	Food, food processing & cookware	Not Available
552	Processing Meats	Food, food processing & cookware	Not Available
553	Treatment Of Hops	Food, food processing & cookware	Not Available
555	Bleaching Agents	Household cleaning & consumer products	Not Available
556	Cigar Cigarettes	Household cleaning & consumer products	Not Available
561	Perfumes Within Detergents And Soaps	Household cleaning & consumer products	Not Available
562	Pipe Accessories	Household cleaning & consumer products	Not Available
563	Soap Detergents	Household cleaning & consumer products	Not Available
564	Soap Dispensers	Household cleaning & consumer products	Not Available
569	Tobacco Smoke Filters	Household cleaning & consumer products	Not Available
571	Coins	Household items	Not Available
578	Making Cigars	Industrial manufacturing & chemical processing	Not Available
579	Manufacture Of Iron Or Steel	Industrial manufacturing & chemical processing	Not Available
580	Manufacture Preparation Of Tobacco Products	Industrial manufacturing & chemical processing	Not Available
581	Paper Making Machines	Industrial manufacturing & chemical processing	Not Available
583	Anchoring Equipment	Marine, shipping & aquaculture	Not Available
596	Acaricides	Agriculture & land management	Not Available
598	Fertiliser Distributors	Agriculture & land management	Not Available
600	Herbicides And Algicides	Agriculture & land management	Not Available
602	Molluscicides	Agriculture & land management	Not Available
603	Nematocides	Agriculture & land management	Not Available
604	Pest Attractants	Agriculture & land management	Not Available
605	Pest Repellants	Agriculture & land management	Not Available
606	Plant Growth Regulators	Agriculture & land management	Not Available
607	Rodenticides(1)	Agriculture & land management	Not Available
608	Rodenticides	Agriculture & land management	Not Available
609	Aftershave	Personal care & cosmetics	Not Available
610	Aftersun Products	Personal care & cosmetics	Not Available
611	Anti Perspirants Or Body Deoderants	Personal care & cosmetics	Not Available
612	Body Washing Or Cleaning Implements	Personal care & cosmetics	Not Available
613	Depilatories	Personal care & cosmetics	Not Available
614	Essential Oils Or Perfumes	Personal care & cosmetics	Not Available
615	Eye Makeup Products	Personal care & cosmetics	Not Available
616	Face Mask Cosmetics	Personal care & cosmetics	Not Available
617	Lip Care Products	Personal care & cosmetics	Not Available
618	Lip Makeup Products	Personal care & cosmetics	Not Available
619	Manicure Pedicure	Personal care & cosmetics	Not Available
630	Toys	Recreation & sports surfaces	Not Available
631	Anthraquinone Dyes	Textiles, leather & furnishings	Not Available
632	Apparel	Textiles, leather & furnishings	Not Available
633	Azo Dyes	Textiles, leather & furnishings	Not Available
634	Buckles	Textiles, leather & furnishings	Not Available
638	Decorating Textiles	Textiles, leather & furnishings	Not Available
640	Embroidering And Tufting	Textiles, leather & furnishings	Not Available
642	Footwear	Textiles, leather & furnishings	Not Available
643	Headwear	Textiles, leather & furnishings	Not Available
647	Multicolour Dyeing	Textiles, leather & furnishings	Not Available
648	Nitro Dyes	Textiles, leather & furnishings	Not Available
650	Purses Luggage Hand Bags	Textiles, leather & furnishings	Not Available
652	Ropes	Textiles, leather & furnishings	Not Available
653	Sewing	Textiles, leather & furnishings	Not Available
655	Slide Fasteners	Textiles, leather & furnishings	Not Available
657	Surface Finishing Of Leather	Textiles, leather & furnishings	Not Available
658	Touch Fasteners	Textiles, leather & furnishings	Not Available
659	Transfer Printing	Textiles, leather & furnishings	Not Available
662	Yarns Or Threads	Textiles, leather & furnishings	Not Available

Pathways

0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Cytochrome P450 2A5	P20852	Mus musculus	Predicted (SEA)	1.63483
Click to view 3D structure	Porphobilinogen deaminase	P08397	Humans	Predicted (SEA)	0.0778492
Click to view 3D structure	Cytochrome P450 2A6	P11509	Humans	Predicted (SEA)	16.0369
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	1790.84
Click to view 3D structure	Cyclin-dependent kinase 5	Q00535	Humans	Predicted (SEA)	1109.2
Click to view 3D structure	Aurora kinase B	Q96GD4	Humans	Predicted (SEA)	1575.59
Click to view 3D structure	Carbonic anhydrase 2	P00918	Humans	Predicted (SEA)	659.694
Click to view 3D structure	Metabotropic glutamate receptor 5	P31424	Rattus norvegicus	Predicted (SEA)	82.5202
Click to view 3D structure	Cytochrome P450 2C19	P33261	Humans	Predicted (SEA)	1291.6
Click to view 3D structure	Serine/threonine-protein kinase pim-1	P11309	Humans	Predicted (SEA)	1585.09
Click to view 3D structure	Dual specificity protein kinase CLK4	Q9HAZ1	Humans	Predicted (SEA)	1455.94
Click to view 3D structure	cAMP-dependent protein kinase catalytic subunit alpha	P17612	Humans	Predicted (SEA)	1496.73
Click to view 3D structure	Rho-associated protein kinase 1	Q13464	Humans	Predicted (SEA)	1685.05
Click to view 3D structure	Tyrosine-protein kinase Lyn	P07948	Humans	Predicted (SEA)	1438.73
Click to view 3D structure	Mitogen-activated protein kinase kinase kinase kinase 2	Q12851	Humans	Predicted (SEA)	1473.37
Click to view 3D structure	Mitogen-activated protein kinase kinase kinase kinase 4	O95819	Humans	Predicted (SEA)	1596.53
Click to view 3D structure	Carbonic anhydrase 12	O43570	Humans	Predicted (SEA)	551.095
Click to view 3D structure	Tyrosine-protein kinase JAK2	O60674	Humans	Predicted (SEA)	1982.9
Click to view 3D structure	Proto-oncogene tyrosine-protein kinase ROS	P08922	Humans	Predicted (SEA)	1243.56
Click to view 3D structure	Cytochrome P450 2D6	P10635	Humans	Predicted (SEA)	2534.15
Click to view 3D structure	Protein RecA	P9WHJ3	Mycobacterium tuberculosis	Predicted (SEA)	452.771
Click to view 3D structure	C-C chemokine receptor type 8	P51685	Humans	Predicted (SEA)	13.935
Click to view 3D structure	Receptor-type tyrosine-protein kinase FLT3	P36888	Humans	Predicted (SEA)	2529.87
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	3618.43
Click to view 3D structure	Sentrin-specific protease 7	Q9BQF6	Humans	Predicted (SEA)	373.676
Click to view 3D structure	Acetylcholinesterase	P22303	Humans	Known	Not Available
Click to view 3D structure	Cytochrome P450 2E1	P05181	Humans	Known	Certain metabolites of xylene have been shown to inhibit pulmonary mixed-function oxidases. (A117)
Click to view 3D structure	Cytochrome P450 4B1	P13584	Humans	Known	Certain metabolites of xylene have been shown to inhibit pulmonary mixed-function oxidases. (A117)
Click to view 3D structure	Transient receptor potential cation channel subfamily A member 1	O75762	Humans	Known	Not Available
Click to view 3D structure	Estrogen receptor	P03372	Humans	Known	Not Available