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

• ChemBase ID: 132712
• Molecular Formular: C11H17ClINO2
• Molecular Mass: 357.61565
• Monoisotopic Mass: 356.99925447
• SMILES: C[C@H](Cc1cc(c(cc1OC)I)OC)N.Cl
• Canonical SMILES: COc1cc(I)c(cc1C[C@H](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/t7-;/m1./s1
• InChIKey: QVFDMWGKHUFODK-OGFXRTJISA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 82864-02-6
• MDL Number: MFCD00153796
• PubChem SID: 24278404; 162226989
• PubChem CID: 11957541

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: soluble; H2O: ≥20 mg/mL
• Apperance: white solid
• Optical Rotation: [α]22/D -12.36°, c = 2 in H2O(lit.)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Drug Control: Home Office Schedule 1

Pharmacology Properties

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

Product Information

• Purity: ≥98% (HPLC)

DETAILS

Sigma Aldrich - D153

Biochem/physiol Actions
Potent and selective 5-HT2 serotonin receptor agonist that crosses the blood-brain barrier; more potent enantiomer of ±-DOI hydrochloride.