(1R)-1-(3,4-dimethoxyphenyl)-2-(methylamino)ethan-1-ol

• ChemBase ID: 175675
• Molecular Formular: C11H17NO3
• Molecular Mass: 211.25758
• Monoisotopic Mass: 211.12084341
• SMILES: c1(c(ccc(c1)[C@H](CNC)O)OC)OC
• Canonical SMILES: CNC[C@@H](c1ccc(c(c1)OC)OC)O
• InChI: InChI=1S/C11H17NO3/c1-12-7-9(13)8-4-5-10(14-2)11(6-8)15-3/h4-6,9,12-13H,7H2,1-3H3/t9-/m0/s1
• InChIKey: QSUCQAULQIAOEP-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R)-1-(3,4-dimethoxyphenyl)-2-(methylamino)ethan-1-ol
• IUPAC Traditional name: (1R)-1-(3,4-dimethoxyphenyl)-2-(methylamino)ethanol
• Synonyms: (αR)-3,4-Dimethoxy-α-[(methylamino)methyl]benzenemethanol; Normacromerine; (-)-Normacromerine

Database IDs

• CAS Number: 41787-64-8
• PubChem SID: 164231585
• PubChem CID: 12888928

CALCULATED PROPERTIES

• Acid pKa: 14.074209
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -2.5676396
• LogD (pH = 7.4): -1.3827429
• Log P: 0.5859172
• Molar Refractivity: 58.1949 cm^3
• Polarizability: 23.029835 Å^3
• Polar Surface Area: 50.72 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Ethyl Acetate; Methanol

DETAILS

Toronto Research Chemicals - N717000

A metabolite of of phenethylamine drugs, normally isolated from Dona Ana cactus, having similar psychoactive properties as Mescaline or Psilocin (P839630).

REFERENCES

• Keller, W., et al.: J. Pharm. Sci., 62, 408 (1973)
• Holshouser, M., et al.: J. Pharm. Sci., 75, 619 (1973)