4-Bromo-2,5-Dimethoxyphenethylamine (2-CB) (CED0032150)

Record Information
Version1.0
Creation Date2016-06-03 13:48:19 UTC
Update Date2026-08-18 00:43:13 UTC
Accession NumberCHEM045906
Identification
Common Name4-Bromo-2,5-Dimethoxyphenethylamine (2-CB)
ClassSmall Molecule
Description
4-Bromo-2,5-Dimethoxyphenethylamine (2-CB) belongs to the methoxybenzenes, a subclass of benzene and substituted derivatives within the organic compounds. This benzenoid compound has the chemical formula C10H14BrNO2 and an average molecular weight of 260.13 g/mol. The compound has been identified in or released from 35 recorded sources. These include electrical and electronic equipment such as antennas, amplifiers, coils, auxiliary devices, and cores yokes or armatures, among 15 others. Within building and construction, it is found in floors, ceilings, roofs, fencing, and ladders, as well as two additional sources. In the category of food, food processing and cookware, it is associated with the processing of meats and fish, and the preparation of wine, sparkling wine, or vinegar. Additionally, it is found in household items such as watch chains and household cleaning and consumer products, specifically soap dispensers, tobacco pipes, and other smoking requisites. Regarding its biological activity, 4-Bromo-2,5-Dimethoxyphenethylamine (2-CB) has two recorded protein targets. It acts as a partial agonist of the 5-hydroxytryptamine receptor 2C (HTR2C) and the 5-hydroxytryptamine receptor 2A (HTR2A).
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
2-(4-Bromo-2,5-dimethoxyphenyl)ethylamineChEBI
4-Bromo-2,5-dimethoxyphenylethylamineChEBI
2C-bMeSH
4-Bromo-2,5-dimethoxyphenethylamineChEBI
Chemical FormulaC10H14BrNO2
Average Molecular Mass260.128 g/mol
Monoisotopic Mass259.021 g/mol
CAS Registry Number66142-81-2
IUPAC Name2-(4-bromo-2,5-dimethoxyphenyl)ethan-1-amine
Traditional Namebdmpea
SMILESCOC1=CC(Br)=C(OC)C=C1CCN
InChI IdentifierInChI=1S/C10H14BrNO2/c1-13-9-6-8(11)10(14-2)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3
InChI KeyYMHOBZXQZVXHBM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassMethoxybenzenes
Direct ParentDimethoxybenzenes
Alternative Parents
Substituents
  • Dimethoxybenzene
  • P-dimethoxybenzene
  • Phenethylamine
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • 2-arylethylamine
  • Alkyl aryl ether
  • Bromobenzene
  • Halobenzene
  • Aralkylamine
  • Aryl halide
  • Aryl bromide
  • Ether
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organobromide
  • Organohalogen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Amine
  • Organopnictogen compound
  • Primary amine
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.2 g/LALOGPS
logP1.99ALOGPS
logP1.84ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)9.68ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area44.48 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity59.84 m³·mol⁻¹ChemAxon
Polarizability23.54 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-001i-9160000000-4feb0ead4ea05d10dc70Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03dl-0090000000-ce1a923a1d805003f40bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-1090000000-d6424051621671bd9c4dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-7290000000-cca25ea059ba67103a59Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0090000000-55ef2a45ab26abe336daNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0190000000-ee1abf8bf995693a12bcNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-08fu-3590000000-6aecc41c4df7e9bd0fefNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
218.0Log mg/kg[120:390]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
495CeilingsBuilding & ConstructionNot Available
496FencingBuilding & ConstructionNot Available
497FloorsBuilding & ConstructionNot Available
498LaddersBuilding & ConstructionNot Available
499RoofsBuilding & ConstructionNot Available
500Stairs And RampsBuilding & ConstructionNot Available
503Tents Or CanopiesBuilding & ConstructionNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
508CoilsElectrical & Electronic EquipmentNot Available
513Cores Yokes Or ArmaturesElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
528MicrophonesElectrical & Electronic EquipmentNot Available
529Power CablesElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
533Sparking PlugsElectrical & Electronic EquipmentNot Available
534Still Video CamerasElectrical & Electronic EquipmentNot Available
535Superconducting Magnets And Superconducting CoilsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
538Thin Magnetic FilmsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
540X Ray TubesElectrical & Electronic EquipmentNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
551Processing FishFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
564Soap DispensersHousehold cleaning & consumer productsNot Available
566Tobacco PipesHousehold cleaning & consumer productsNot Available
577Watch ChainsHousehold itemsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
583Anchoring EquipmentMarine, shipping & aquacultureNot Available
584BuoysMarine, shipping & aquacultureNot Available
589Life BuoysMarine, shipping & aquacultureNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
593Nautical InstrumentsMarine, shipping & aquacultureNot Available
601Lawn MowersAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
620Card GamesRecreation & sports surfacesNot Available
621Chutes And SlidesRecreation & sports surfacesNot Available
622Game AccessoriesRecreation & sports surfacesNot Available
624Merry Go RoundsRecreation & sports surfacesNot Available
625Racing SportsRecreation & sports surfacesNot Available
627Roulette GamesRecreation & sports surfacesNot Available
630ToysRecreation & sports surfacesNot Available
634BucklesTextiles, leather & furnishingsNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
644Hook Or Eye FastenersTextiles, leather & furnishingsNot Available
649Pins ClothesTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
651Purses Money Bags WalletsTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
655Slide FastenersTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)2.95827
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP08909RatPredicted (SEA)1.32344
Click to view 3D structure5-hydroxytryptamine receptor 2AP14842Rattus norvegicusPredicted (SEA)2.95827
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)9.49761
Click to view 3D structure5-hydroxytryptamine receptor 1AP19327Rattus norvegicusPredicted (SEA)32.1517
Trace amine-associated receptor 1 structureClick to view 3D structureTrace amine-associated receptor 1Q96RJ0HumansPredicted (SEA)2.10193
Click to view 3D structure5-hydroxytryptamine receptor 2BP30994Rattus norvegicusPredicted (SEA)2.72472
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)52.0811
5-hydroxytryptamine receptor 1A structureClick to view 3D structure5-hydroxytryptamine receptor 1AP08908HumansPredicted (SEA)150.171
5-hydroxytryptamine receptor 6 structureClick to view 3D structure5-hydroxytryptamine receptor 6P50406HumansPredicted (SEA)158.735
5-hydroxytryptamine receptor 7 structureClick to view 3D structure5-hydroxytryptamine receptor 7P34969HumansPredicted (SEA)198.126
5-hydroxytryptamine receptor 1B structureClick to view 3D structure5-hydroxytryptamine receptor 1BP28222HumansPredicted (SEA)104.084
Click to view 3D structure5-hydroxytryptamine receptor 1BP28564Rattus norvegicusPredicted (SEA)131.643
5-hydroxytryptamine receptor 1D structureClick to view 3D structure5-hydroxytryptamine receptor 1DP28221HumansPredicted (SEA)263.13
Click to view 3D structureNorepinephrine transporterQ9WTR4Rattus norvegicusPredicted (SEA)99.8806
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)413.535
Click to view 3D structureTrace amine-associated receptor 1Q8HZ64Macaca mulattaPredicted (SEA)3.03612
5-hydroxytryptamine receptor 5A structureClick to view 3D structure5-hydroxytryptamine receptor 5AP47898HumansPredicted (SEA)205.911
Alpha-2B adrenergic receptor structureClick to view 3D structureAlpha-2B adrenergic receptorP18089HumansPredicted (SEA)401.001
Click to view 3D structureSodium-dependent serotonin transporterP31652Rattus norvegicusPredicted (SEA)402.792
Click to view 3D structureSodium-dependent dopamine transporterP23977Rattus norvegicusPredicted (SEA)309.451
Polyunsaturated fatty acid 5-lipoxygenase structureClick to view 3D structurePolyunsaturated fatty acid 5-lipoxygenaseP09917HumansPredicted (SEA)242.267
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)841.472
Alpha-2C adrenergic receptor structureClick to view 3D structureAlpha-2C adrenergic receptorP18825HumansPredicted (SEA)622.794
5-hydroxytryptamine receptor 3A structureClick to view 3D structure5-hydroxytryptamine receptor 3AP46098HumansPredicted (SEA)435.878
Concentrations
Not Available
External Links
DrugBank IDDB01537
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia Link2C-B
Chemspider IDNot Available
ChEBI ID189669
PubChem Compound ID98527
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References