[2-(1H-indol-3-yl)ethyl]dimethylamine

• ChemBase ID: 1284
• Molecular Formular: C12H16N2
• Molecular Mass: 188.26884
• Monoisotopic Mass: 188.13134852
• SMILES: N(CCc1c2c([nH]c1)cccc2)(C)C
• Canonical SMILES: CN(CCc1c[nH]c2c1cccc2)C
• InChI: InChI=1S/C12H16N2/c1-14(2)8-7-10-9-13-12-6-4-3-5-11(10)12/h3-6,9,13H,7-8H2,1-2H3
• InChIKey: DMULVCHRPCFFGV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [2-(1H-indol-3-yl)ethyl]dimethylamine
• IUPAC Traditional name: (psychogenic); dimethyltryptamine
• Synonyms: Dimethyltryptamine

Database IDs

• CAS Number: 61-50-7
• PubChem SID: 46507463; 160964744
• PubChem CID: 6089
• CHEBI ID: 28969
• CHEMBL: 12420
• Chemspider ID: 5864
• DrugBank ID: DB01488
• IUPHAR ligand ID: 141
• KEGG ID: C08302
• Unique Ingredient Identifier: WUB601BHAA
• Wikipedia Title: Dimethyltryptamine

CALCULATED PROPERTIES

JChem

• Acid pKa: 17.164974
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): -1.0906249
• LogD (pH = 7.4): 0.17050894
• Log P: 2.3020658
• Molar Refractivity: 60.4422 cm^3
• Polarizability: 24.46552 Å^3
• Polar Surface Area: 19.03 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.41
• LOG S: -2.05
• Solubility (Water): 1.69e+00 g/l

PROPERTIES

Physical Property

• Melting Point: 40°C (104°F)
• Boiling Point: 160°C (320°F) (@ 0.6 Torr also reported as 80 – 135 °C @ 0.03 Torr)
• Density: 1.099g/ml g/cm^3

Pharmacology Properties

• Admin Routes: Oral (with an MAOI), Insufflated, Rectal, Smoked (or vaporized), IM, IV
• Legal Status: CD Lic (UK); S9 (Australia); Schedule I (US); Schedule III (Canada)

DETAILS

DrugBank - DB01488

• Drug Groups: illicit; experimental
• Description: An N-methylated indoleamine derivative, a serotonergic hallucinogen found in several plants, especially Prestonia amazonica (Apocynaceae) and in mammalian brain, blood, and urine. It apparently acts as an agonist at some types of serotonin receptors and an antagonist at others. [PubChem]
• Indication: Some people use this compound as a psychedelic inducing agent.
• References: Strassman RJ, Qualls CR: Dose-response study of N,N-dimethyltryptamine in humans. I. Neuroendocrine, autonomic, and cardiovascular effects. Arch Gen Psychiatry. 1994 Feb;51(2):85-97. [Pubmed] ; Callaway JC: A proposed mechanism for the visions of dream sleep. Med Hypotheses. 1988 Jun;26(2):119-24. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Strassman RJ, Qualls CR: Dose-response study of N,N-dimethyltryptamine in humans. I. Neuroendocrine, autonomic, and cardiovascular effects. Arch Gen Psychiatry. 1994 Feb;51(2):85-97. Pubmed
• Callaway JC: A proposed mechanism for the visions of dream sleep. Med Hypotheses. 1988 Jun;26(2):119-24. Pubmed