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

• ChemBase ID: 1252
• Molecular Formular: C11H14N2
• Molecular Mass: 174.24226
• Monoisotopic Mass: 174.11569846
• SMILES: [nH]1c2c(c(CC(N)C)c1)cccc2
• Canonical SMILES: CC(Cc1c[nH]c2c1cccc2)N
• InChI: InChI=1S/C11H14N2/c1-8(12)6-9-7-13-11-5-3-2-4-10(9)11/h2-5,7-8,13H,6,12H2,1H3
• InChIKey: QSQQQURBVYWZKJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(1H-indol-3-yl)propan-2-amine
• IUPAC Traditional name: α-methyltryptamine; 1-(1H-indol-3-yl)propan-2-amine
• Synonyms: Alpha-methyltryptamine; 3-(2-AMINOPROPYL)INDOLE; (±)-α-Methyltryptamine Hydrochloride; 164 E; 2-(1H-Indol-3-yl)-1-methylethylamine Hydrochloride; 3-(2-Aminopropyl)-1H-indole Hydrochloride; 3-(2-Aminopropyl)indole Hydrochloride; NSC 97069 Hydrochloride; Ro 3-0926; U 14 Hydrochloride; Indopan Hydrochloride; α-Methyl-3-indoleethanamine Hydrochloride; α-Methyl-1H-indole-3-ethanamine Hydrochloride; α-Methyltryptamine Hydrochloride; Alpha-methyltryptamine

Database IDs

• CAS Number: 299-26-3; 879-36-7
• PubChem SID: 46507024; 160964712
• PubChem CID: 9287

CALCULATED PROPERTIES

JChem

• Acid pKa: 17.137882
• H Acceptors: 1
• H Donor: 2
• LogD (pH = 5.5): -1.1141208
• LogD (pH = 7.4): -0.53133327
• Log P: 1.9030125
• Molar Refractivity: 54.7917 cm^3
• Polarizability: 22.619116 Å^3
• Polar Surface Area: 41.81 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.0
• LOG S: -2.18
• Solubility (Water): 1.15e+00 g/l

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Light Beige Solid
• Melting Point: 213-215°C

Safety Information

• Storage Condition: Refrigerator

Pharmacology Properties

• Mechanism of Action: 5-HT2A receptor agonist; Monoamine oxidase inhibitor and a stimulant; Sympathomimetic

Product Information

• Purity: 98%
• Application(s): Psychostimulant; Psychotonic

DETAILS

DrugBank - DB01446

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

Toronto Research Chemicals - M331925

α-Methyltryptamine is a methylated Tryptamine with psychedelic, stimulant and entactogenic properties. α-Methyltryptamine is a non-selective serotonin receptor agonist. α-Methyltryptamine acts as relatively balanced releasing agent of serotonin, norepinep

REFERENCES

• Nagain, F. et al.: Eur. J. Pharmacol., 559, 132 (2007)
• Nonaka, R. et al.: Biol. Pharmac. Bull., 30, 2328 (2007)