1-(4-bromo-2,5-dimethoxyphenyl)propan-2-amine

• ChemBase ID: 1281
• Molecular Formular: C11H16BrNO2
• Molecular Mass: 274.15424
• Monoisotopic Mass: 273.03644076
• SMILES: Brc1c(OC)cc(CC(N)C)c(OC)c1
• Canonical SMILES: COc1cc(Br)c(cc1CC(N)C)OC
• InChI: InChI=1S/C11H16BrNO2/c1-7(13)4-8-5-11(15-3)9(12)6-10(8)14-2/h5-7H,4,13H2,1-3H3
• InChIKey: FXMWUTGUCAKGQL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(4-bromo-2,5-dimethoxyphenyl)propan-2-amine
• IUPAC Traditional name: dob-4
• Synonyms: 4-Bromo-2,5-dimethoxy-amphetamine; 2,5-Dimethoxy-4-bromoamphetamine; 4-Bromo-2,5-dimethoxyamphetamine; 4-Bromo-2,5-dimethoxy-α-methylbenzeneethanamine; (+/-)-1-(4-Bromo-2,5-dimethoxyphenyl)-2-aminopropane; (+/-)-2,5-Dimethoxy-4-bromoamphetamine; Brolamfetamine; DOB; dl-2,5-Dimethoxy-4-bromoamphetamine

Database IDs

• CAS Number: 32156-26-6; 64638-07-9
• PubChem SID: 160964741; 46507989
• PubChem CID: 62065
• CHEMBL: 6607
• Chemspider ID: 55902
• DrugBank ID: DB01484
• IUPHAR ligand ID: 163
• Wikipedia Title: 2,5-Dimethoxy-4-bromoamphetamine

CALCULATED PROPERTIES

JChem

• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.75737745
• LogD (pH = 7.4): -0.13536483
• Log P: 2.2576606
• Molar Refractivity: 64.2544 cm^3
• Polarizability: 25.121777 Å^3
• Polar Surface Area: 44.48 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.53
• LOG S: -3.46
• Solubility (Water): 9.48e-02 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Solid
• Melting Point: 63-65 °C; 207-208 °C (hydrochloride); 67-70°C

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer

DETAILS

DrugBank - DB01484

Drug information: illicit; experimental

Toronto Research Chemicals - D446585

2,5-Dimethoxy-4-bromoamphetamine (DOB) is one of the potent hallucinogenic phenylalkylamines with neurotoxic properties.

REFERENCES

• Monte, A., et al.: J. Med. Chem., 39, 2953 (1996)
• Pedersen, W., et al.: Addiction, 94, 1695 (1996)
• Kanamori, T., et al.: J. Anal. Toxicol., 26, 61 (1996)