1-(1H-indol-3-yl)butan-2-amine

• ChemBase ID: 1331
• Molecular Formular: C12H16N2
• Molecular Mass: 188.26884
• Monoisotopic Mass: 188.13134852
• SMILES: [nH]1c2c(c(CC(N)CC)c1)cccc2
• Canonical SMILES: CCC(Cc1c[nH]c2c1cccc2)N
• InChI: InChI=1S/C12H16N2/c1-2-10(13)7-9-8-14-12-6-4-3-5-11(9)12/h3-6,8,10,14H,2,7,13H2,1H3
• InChIKey: ZXUMUPVQYAFTLF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(1H-indol-3-yl)butan-2-amine
• IUPAC Traditional name: α-ethyltryptamine; 1-(1H-indol-3-yl)butan-2-amine
• Synonyms: Alpha-ethyltryptamine; Alpha-Ethyltryptamine; 3-(2-Aminobutyl)indole; Etryptamine

Database IDs

• CAS Number: 2235-90-7
• PubChem SID: 160964791; 46507084
• PubChem CID: 8367

CALCULATED PROPERTIES

JChem

• Acid pKa: 17.134817
• H Acceptors: 1
• H Donor: 2
• LogD (pH = 5.5): -0.5927
• LogD (pH = 7.4): -0.03214526
• Log P: 2.425535
• Molar Refractivity: 59.3157 cm^3
• Polarizability: 24.465405 Å^3
• Polar Surface Area: 41.81 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.55
• LOG S: -2.59
• Solubility (Water): 4.81e-01 g/l

PROPERTIES

Physical Property

• Solubility: 0.51 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)]

Pharmacology Properties

• Mechanism of Action: CNS stimulant; MAO inhibitor

Product Information

• Application(s): Antidepressant; CNS stimulant; Psychostimulant

DETAILS

DrugBank - DB01546

• Drug Groups: illicit; experimental
• External Links: Wikipedia

REFERENCES

• Heinzelman, R.V. et al., J.O.C., 1960, 25, 1548, (synth)
• U.K. Pat., 1963, 933 786; CA, 60, 1705, (synth)
• Cerletti, A. et al., Adv. Pharmacol., 1968, 6, 233, (pharmacol)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, AJB250