Dichloromethane (CED0000830)

Record Information
Version1.0
Creation Date2009-03-06 18:58:02 UTC
Update Date2026-08-26 00:12:17 UTC
Accession NumberCHEM000076
Identification
Common NameDichloromethane
ClassSmall Molecule
Description
Dichloromethane (CH2Cl2) is an exogenous organic compound with an average molecular weight of 84.93 g/mol. Dichloromethane belongs to the halomethanes, a subclass of alkyl halides within the organic compounds. At room temperature, this organohalogen compound exists as a liquid. Its industrial applications include use as a solvent (PMC5572480, PMC8671471), a refrigerant (PMC5572480, PMC8671471), and a polar aprotic solvent. Biologically, it is identified as a carcinogenic agent (PMC5572480, PMC8671471) and an antioxidant (PMC13022387). The compound is found in or released from 67 recorded sources, including electrical and electronic equipment, household cleaning and consumer products, building and construction, aquatic systems and sediments, and drinking water and water supply. It is also associated with food, food processing, and cookware. Recorded exposure routes include oral, touch, and inhalation, the latter of which is supported by literature (PMC11746923). Health effects associated with dichloromethane include nausea (PMC11746923), headache (PMC11746923), and dizziness (PMC11746923). It is linked to cancer (PMC5435304), pancreatic cancer (PMC6394840), an increase in non-Hodgkin lymphoma (PMC5435304), and breast cancer (PMC11425761, PMC12327356, PMC5435304). Dichloromethane targets four proteins. It binds to and inhibits the estrogen receptor beta (ESR2) and estrogen receptor (ESR1), causing endocrine disruption in humans. Additionally, it targets hemoglobin subunit beta (HBB) and hemoglobin subunit alpha (HBA1); it is metabolized into carbon monoxide, which binds to hemoglobin to produce dose-dependent increases in carboxyhemoglobin, resulting in neurological dysfunction and reduced oxygen transport characteristic of carboxyhemoglobinemia.
Contaminant Type
  • Food Toxin
  • Household Toxin
  • Human Neurotoxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Organic Compound
  • Organochloride
  • PMT
  • Pesticide
  • Pollutant
  • Solvent
  • Synthetic Compound
Chemical Structure
Synonyms
ValueSource
Chlorure de methyleneChEBI
DCMChEBI
DichlormethanChEBI
Methane dichlorideChEBI
MethylenchloridChEBI
Methylene bichlorideChEBI
Methylene chlorideChEBI
Methylene dichlorideChEBI
AerotheneHMDB
Aerothene MMHMDB
Bichloride, methyleneHMDB
CH2CL2HMDB
Chloride, methyleneHMDB
Dichloride, methyleneHMDB
Dichloro-methaneHMDB
Dichloromethane, acsHMDB
Dichloromethane, NFHMDB
Distillex DS3HMDB
DriveritHMDB
Freon 30HMDB
m-Clean DHMDB
MethokloneHMDB
Metylenu chlorekHMDB
NarkotilHMDB
NevolinHMDB
R 30HMDB
SalesthinHMDB
SolaesthinHMDB
SolmethineHMDB
Chemical FormulaCH2Cl2
Average Molecular Mass84.933 g/mol
Monoisotopic Mass83.953 g/mol
CAS Registry Number1975-09-02
IUPAC Namedichloromethane
Traditional Namemethylene chloride
SMILESClCCl
InChI IdentifierInChI=1S/CH2Cl2/c2-1-3/h1H2
InChI KeyYMWUJEATGCHHMB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as halomethanes. These are organic compounds in which at least one of the four hydrogen atoms of methane (CH4) are replaced by halogen atoms.
KingdomOrganic compounds
Super ClassOrganohalogen compounds
ClassAlkyl halides
Sub ClassHalomethanes
Direct ParentHalomethanes
Alternative Parents
Substituents
  • Halomethane
  • Hydrocarbon derivative
  • Organochloride
  • Alkyl chloride
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
Applications
Biological Roles
Chemical Roles
Organoleptic EffectsNot Available
Physical Properties
StateLiquid
AppearanceColorless liquid.
Experimental Properties
PropertyValue
Melting Point-96.8°C
Boiling PointNot Available
Solubility13 mg/mL at 25°C
Predicted Properties
PropertyValueSource
Water Solubility17.5 g/LALOGPS
logP1.12ALOGPS
logP1.29ChemAxon
logS-0.69ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity16.44 m³·mol⁻¹ChemAxon
Polarizability6.53 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-0002-9000000000-fea8e21d8ce299fd6c73Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-000t-9000000000-3c727a0b79ead1d0afc9Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0002-9000000000-fea8e21d8ce299fd6c73Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-000t-9000000000-3c727a0b79ead1d0afc9Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-001i-9000000000-a20182f85c9e395e5511Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-9000000000-9fdeb81f96b30affd700Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-9000000000-9fdeb81f96b30affd700Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-9000000000-9fdeb81f96b30affd700Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-9000000000-3641e00693a6eab28168Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-9000000000-3641e00693a6eab28168Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-9000000000-3641e00693a6eab28168Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-9000000000-cd27483dddc3a8ea1a54Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-9000000000-cd27483dddc3a8ea1a54Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-9000000000-cd27483dddc3a8ea1a54Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-9000000000-fddbf58cbca8e803abceNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-9000000000-fddbf58cbca8e803abceNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001j-9000000000-ed36dd35150f69631b13Not AvailableView Spectrum
MSMS Spectrumsplash10-000t-9000000000-6ce0b546ffcfe5b5cf7eNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityMethylene chloride targets the lungs, blood system, and nervous system. In the lungs its metabolites damage Clara cells. It is also metabolized into carbon monoxide, which binds to hemoglobin to produce dose-dependent increases in carboxyhemoglobin. This results in the reduced oxygen transport and neurological dysfunction characteristic of carboxyhemoglobinemia (carbon monoxide poisoning). Methylene chloride is also believed to cause neurotoxicity by interfering with signal transmission in a manner similar to general anesthetics. Certain metabolites, such as formaldehyde, may result in carcinogenic effects by causing DNA single strand breaks, DNA-protein crosslinks, and other mutations. (11, 8)
Carcinogenicity (IARC Classification)2A, probably carcinogenic to humans. (7)
Minimum Risk LevelAcute Inhalation: 0.6 ppm (6) Intermediate Inhalation: 0.3 ppm (6) Chronic Inhalation: 0.3 ppm (6) Acute Oral: 0.2 mg/kg/day (6) Chronic Oral: 0.06 mg/kg/day (6)
SymptomsBreathing large amounts of methylene chloride causes dizziness, nausea, tingling or numbness of the finger and toes, loss of concentration, and reduced hand-eye coordination. Very high concentrations can lead to unconciousness, coma, and death. Skin contact with methylene chloride causes burning and redness of the skin. (8, 9)
TreatmentTreatment of methylene chloride exposure is mainly symptomatic. Ingested methylene chloride may be removed by emesis and/or gastric lavage, and activated charcoal. Hyperbaric oxygen may be used to treat the carbon monoxide poisoning that can result from inhalation of methylene chloride. (10)
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
437.0mg/kgNot AvailableMouseLD50IntraperitonealexperimentalT14
6460.0mg/kgNot AvailableMouseLD50SubcutaneousexperimentalT14
1600.0mg/kgNot AvailableRatLD50OralexperimentalT32
14400.0ppmNot AvailableMouseLC50Inhalation (7 hours)experimentalT14
Health Effects
Health EffectRelationshipDirectionReference
cancerassociated_withNot AvailablePMC5435304
dizzinessassociated_withNot AvailablePMC11746923 , PMC11746923
breast cancerassociated_withNot AvailablePMC11425761 , PMC11425761 , PMC12327356
breast cancerassociated_withincreasePMC5435304
headacheassociated_withNot AvailablePMC11746923
nauseaassociated_withNot AvailablePMC11746923
pancreatic cancerassociated_withNot AvailablePMC6394840
non-Hodgkin lymphomaassociated_withincreasePMC5435304
Exposure Sources
Source IDSourceSectorReference
3Irrigation waterAgriculture & land managementNot Available
10InsecticidesAgriculture & land managementNot Available
27Water CoolersAppliances, HVAC & refrigerantsNot Available
43Water heatersAppliances, HVAC & refrigerantsNot Available
50GroundwaterAquatic systems & sedimentsNot Available
51Surface waterAquatic systems & sedimentsNot Available
52SeawaterAquatic systems & sedimentsNot Available
53FreshwaterAquatic systems & sedimentsNot Available
70Stormwater runoffAutomotive & urban infrastructureNot Available
88Waterproofing spraysBuilding & ConstructionNot Available
115Drinking waterDrinking water & water supplyNot Available
116Tap waterDrinking water & water supplyNot Available
117Bottled waterDrinking water & water supplyNot Available
118Desalinated waterDrinking water & water supplyNot Available
181Ballast waterMarine, shipping & aquacultureNot Available
182Bilge waterMarine, shipping & aquacultureNot Available
233BrushesPersonal care & cosmeticsNot Available
468Industrial wastewaterWastewater, sanitation & biosolidsNot Available
470Wastewater treatment effluentWastewater, sanitation & biosolidsNot Available
475Mine wastewaterWastewater, sanitation & biosolidsNot Available
477Wastewater, unspecifiedWastewater, sanitation & biosolidsNot Available
490Personal care & cosmeticsNot Available
494Food contact materialsFood, food processing & cookwareNot Available
495CeilingsBuilding & ConstructionNot Available
497FloorsBuilding & ConstructionNot Available
501Sunshades Awnings Or Outside ScreensBuilding & ConstructionNot Available
502Sunshades Awnings Or Outside ScreensBuilding & ConstructionNot Available
504Adjustable ResistorsElectrical & Electronic EquipmentNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
508CoilsElectrical & Electronic EquipmentNot Available
510Communication Cables Or ConductorsElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
512ContactsElectrical & Electronic EquipmentNot Available
513Cores Yokes Or ArmaturesElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
523Gas Filled Discharge Tubes With Solid CathodeElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
529Power CablesElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
531RelaysElectrical & Electronic EquipmentNot Available
535Superconducting Magnets And Superconducting CoilsElectrical & Electronic EquipmentNot Available
536Superconductive Or Hyperconductive Conductors Cables Or Transmission LinesElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
538Thin Magnetic FilmsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
551Processing FishFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
553Treatment Of HopsFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
584BuoysMarine, shipping & aquacultureNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
593Nautical InstrumentsMarine, shipping & aquacultureNot Available
594Ship HullsMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
597ChemosterilantsAgriculture & land managementNot Available
598Fertiliser DistributorsAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
631Anthraquinone DyesTextiles, leather & furnishingsNot Available
632ApparelTextiles, leather & furnishingsNot Available
633Azo DyesTextiles, leather & furnishingsNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
639Degreasing LeatherTextiles, leather & furnishingsNot Available
640Embroidering And TuftingTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
645Inorganic FibresTextiles, leather & furnishingsNot Available
647Multicolour DyeingTextiles, leather & furnishingsNot Available
648Nitro DyesTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
658Touch FastenersTextiles, leather & furnishingsNot Available
659Transfer PrintingTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structure3-ketoacyl-CoA synthase 20Q9FG87Arabidopsis thalianaPredicted (SEA)11.2881
Click to view 3D structurePutative agmatine deiminaseQ8DW17Streptococcus mutans serotype c (strain ATCC 700610 / UA159)Predicted (SEA)60.1774
Click to view 3D structureProtein RecAP9WHJ3Mycobacterium tuberculosisPredicted (SEA)7779.24
Click to view 3D structure3-ketoacyl-CoA synthase 18Q38860Arabidopsis thalianaPredicted (SEA)2645.63
Replicase polyprotein 1ab structureClick to view 3D structureReplicase polyprotein 1abP0DTD1SARS-CoV-2Predicted (SEA)7783.83
Tyrosine-protein kinase JAK2 structureClick to view 3D structureTyrosine-protein kinase JAK2O60674HumansPredicted (SEA)7784.46
Click to view 3D structureHeat shock factor protein 1P38532Mus musculusPredicted (SEA)7783.29
Click to view 3D structureATP-dependent molecular chaperone HSP82C4YTQ8Candida albicans (strain WO-1) (Yeast)Predicted (SEA)7783.99
Acetylcholinesterase structureClick to view 3D structureAcetylcholinesteraseP22303HumansPredicted (SEA)7784.53
E3 ubiquitin-protein ligase RNF4 structureClick to view 3D structureE3 ubiquitin-protein ligase RNF4P78317HumansPredicted (SEA)6725.71
Transient receptor potential cation channel subfamily A member 1 structureClick to view 3D structureTransient receptor potential cation channel subfamily A member 1O75762HumansPredicted (SEA)7783.75
Click to view 3D structureSigma non-opioid intracellular receptor 1Q60492Cavia porcellusPredicted (SEA)7784.38
Sodium-dependent dopamine transporter structureClick to view 3D structureSodium-dependent dopamine transporterQ01959HumansPredicted (SEA)7784.61
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)7784.61
Click to view 3D structureDNA damage-inducible transcript 3 proteinP35639Mus musculusPredicted (SEA)7784.38
X-box-binding protein 1 structureClick to view 3D structureX-box-binding protein 1P17861HumansPredicted (SEA)7784.38
Folliculin-interacting protein 1 structureClick to view 3D structureFolliculin-interacting protein 1Q8TF40HumansPredicted (SEA)6578.96
Click to view 3D structureLarge neutral amino acids transporter small subunit 1Q63016Rattus norvegicusPredicted (SEA)7076.57
Alpha-2C adrenergic receptor structureClick to view 3D structureAlpha-2C adrenergic receptorP18825HumansPredicted (SEA)7784.61
Sodium-dependent noradrenaline transporter structureClick to view 3D structureSodium-dependent noradrenaline transporterP23975HumansPredicted (SEA)7784.61
Histamine H3 receptor structureClick to view 3D structureHistamine H3 receptorQ9Y5N1HumansPredicted (SEA)7784.53
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)7784.69
Click to view 3D structureSodium-dependent serotonin transporterP31652Rattus norvegicusPredicted (SEA)7784.46
Click to view 3D structureRetinal dehydrogenase 2O93344Gallus gallusPredicted (SEA)3733.96
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)7784.61
Estrogen receptor structureClick to view 3D structureEstrogen receptorP03372HumansKnownCauses endocrine disruption in humans by binding to and inhibiting the estrogen receptor. (A590)
Estrogen receptor beta structureClick to view 3D structureEstrogen receptor betaQ92731HumansKnownCauses endocrine disruption in humans by binding to and inhibiting the estrogen receptor. (A590)
Hemoglobin subunit alpha structureClick to view 3D structureHemoglobin subunit alphaP69905HumansKnownMethylene chloride is metabolized into carbon monoxide, which binds to hemoglobin to produce dose-dependent increases in carboxyhemoglobin. This results in the reduced oxygen transport and neurological dysfunction characteristic of carboxyhemoglobinemia (carbon monoxide poisoning). (L188)
Hemoglobin subunit beta structureClick to view 3D structureHemoglobin subunit betaP68871HumansKnownMethylene chloride is metabolized into carbon monoxide, which binds to hemoglobin to produce dose-dependent increases in carboxyhemoglobin. This results in the reduced oxygen transport and neurological dysfunction characteristic of carboxyhemoglobinemia (carbon monoxide poisoning). (L188)
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0031548
FooDB IDFDB008159
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-681
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDichloromethane
Chemspider ID6104
ChEBI ID15767
PubChem Compound ID6344
Kegg Compound IDC02271
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11884241
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19091298
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=8465711
4. Jin W, Shi Q, Hong C, Cheng Y, Ma Z, Qu H: Cytotoxic properties of thiophenes from Echinops grijissi Hance. Phytomedicine. 2008 Sep;15(9):768-74. Epub 2008 Feb 20.
5. Barreiro Arcos ML, Cremaschi G, Werner S, Coussio J, Ferraro G, Anesini C: Tilia cordata Mill. Extracts and scopoletin (isolated compound): differential cell growth effects on lymphocytes. Phytother Res. 2006 Jan;20(1):34-40.
6. Matheus ME, Berrondo LF, Vieitas EC, Menezes FS, Fernandes PD: Evaluation of the antinociceptive properties from Brillantaisia palisotii Lindau stems extracts. J Ethnopharmacol. 2005 Dec 1;102(3):377-81. Epub 2005 Aug 1.
7. Khan MR, Omoloso AD: Antibacterial and antifungal activities of Dracontomelon dao. Fitoterapia. 2002 Jul;73(4):327-30.
8. Meyer JJ, Dilika F: Antibacterial activity of Helichrysum pedunculatum used in circumcision rites. J Ethnopharmacol. 1996 Jul 26;53(1):51-4.
9. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.