{2-[4-(benzyloxy)-1H-indol-3-yl](2H4)ethyl}dimethylamine

• ChemBase ID: 161941
• Molecular Formular: C19H22N2O
• Molecular Mass: 294.39078
• Monoisotopic Mass: 294.17321333
• SMILES: c1cc(c2c(c1)[nH]cc2CCN(C)C)OCc1ccccc1
• Canonical SMILES: CN(CCc1c[nH]c2c1c(ccc2)OCc1ccccc1)C
• InChI: InChI=1S/C19H22N2O/c1-21(2)12-11-16-13-20-17-9-6-10-18(19(16)17)22-14-15-7-4-3-5-8-15/h3-10,13,20H,11-12,14H2,1-2H3
• InChIKey: LHERKDDDEMCCCU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {2-[4-(benzyloxy)-1H-indol-3-yl](^2H₄)ethyl}dimethylamine
• IUPAC Traditional name: {2-[4-(benzyloxy)-1H-indol-3-yl](^2H₄)ethyl}dimethylamine
• Synonyms: N,N-Dimethyl-4-(phenylmethoxy)-1H-indole-3-ethanamine-d4; 4-(Benzyloxy)-3-[2-(dimethylamino)ethyl]indole-d4; 4-(Benzyloxy)-N,N-dimethyltryptamine-d4; O-Benzyl Psilocin-d4; SM-9018; Lullan; Perospirone Hydrochloride Trihydrate; (3aR,7aS)-rel-2-[4-[4-(1,2-Benzisothiazol-3-yl)-1-piperazinyl]butyl]hexahydro-1H-isoindole-1,3(2H)-dione Hydrochloride Trihydrate

Database IDs

• CAS Number: 129273-38-7
• PubChem SID: 162256076
• PubChem CID: 71313927

CALCULATED PROPERTIES

• Acid pKa: 17.42116
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.47738546
• LogD (pH = 7.4): 1.7424752
• Log P: 3.8688676
• Molar Refractivity: 91.518 cm^3
• Polarizability: 36.644203 Å^3
• Polar Surface Area: 28.26 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol; Methanol
• Apperance: Brown Semi-Solid; White Solid
• Melting Point: 95-97°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - B288712

Protected precursor to labelled Psilocin.

Toronto Research Chemicals - P288900

Serotonin (5-HT2) and dopamine (D2) antagonist (SDA).

REFERENCES

• Albers, C., et al.: J. Pharm. Pharmacol., 54, 1265 (2002)
• Pickens, J., et al.: Chem. Biol., 9, 215 (2002)
• Sard, H., et al.: Bioorg. Med. Chem. Lett., 15, 4555 (2002)
• Kato, T., et al.: Jpn. J. Pharmacol., 54, 478 (1990)
• Sakamoto, H., et al.: Pharmacol. Biochem. Behav., 60, 873 (1990)
• Onrust, S.V., et al.: CNS Drugs, 15, 329 (1990)