1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine hydrochloride

• ChemBase ID: 134033
• Molecular Formular: C11H17ClINO2
• Molecular Mass: 357.61565
• Monoisotopic Mass: 356.99925447
• SMILES: CC(Cc1cc(c(cc1OC)I)OC)N.Cl
• Canonical SMILES: COc1cc(I)c(cc1CC(N)C)OC.Cl
• InChI: InChI=1S/C11H16INO2.ClH/c1-7(13)4-8-5-11(15-3)9(12)6-10(8)14-2;/h5-7H,4,13H2,1-3H3;1H
• InChIKey: QVFDMWGKHUFODK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine hydrochloride
• IUPAC Traditional name: 1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine hydrochloride
• Synonyms: (±)-DOI; (±)-1-(2,5-Dimethoxy-4-iodophenyl)-2-aminopropane hydrochloride; (±)-2,5-Dimethoxy-4-iodoamphetamine hydrochloride; (±)-DOI hydrochloride

Database IDs

• CAS Number: 42203-78-1
• MDL Number: MFCD00055199
• PubChem SID: 24278092; 162228310
• PubChem CID: 170617

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.5972032
• LogD (pH = 7.4): 0.024494693
• Log P: 2.4178524
• Molar Refractivity: 69.9941 cm^3
• Polarizability: 27.461819 Å^3
• Polar Surface Area: 44.48 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: ethanol: soluble2 mg/mL; H2O: soluble10 mg/mL
• Apperance: white to off-white solid

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 22-26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Drug Control: Home Office Schedule 1; regulated under CDSA - not available from Sigma-Aldrich Canada

Pharmacology Properties

• Gene Information: human ... HTR2A(3356), HTR2B(3357), HTR2C(3358)

Product Information

• Purity: ≥98% (HPLC)

DETAILS

Sigma Aldrich - D101

Biochem/physiol Actions
(±)-DOI hydrochloride is a potent and selective 5-HT2 serotonin receptor agonist that crosses the blood-brain barrier, increases dopamine turnover and the treatment with DOI counteracted the expression of the nicotine-induced locomotor and neurochemical sensitization, but had no effect on nicotine-induced behavioral disinhibition. The responses to DOI provide evidence that of these receptors are abundant in the cortex, and show relatively lower levels in hippocampus and cerebellum.