N,N-Dibenzyltryptamine

ID: ALA1779158

Chembl Id: CHEMBL1779158

Cas Number: 15741-80-7

PubChem CID: 45584

Max Phase: Preclinical

Molecular Formula: C24H24N2

Molecular Weight: 340.47

Molecule Type: Small molecule

Names and Identifiers

Synonyms: N,N-Dibenzyltryptamine | N,N-Dibenzyltryptamine|N,N-dibenzyl-2-(1H-indol-3-yl)ethanamine|15741-80-7|1H-Indole-3-ethanamine, N,N-bis(phenylmethyl)-|CHEMBL1779158|N,N-Dibenzyltryptamin|N,N-dibenzyl-tryptamine|N,N-Dibenzyl-3-(2-aminoethyl)-1H-indole|SCHEMBL3335605|DTXSID60166257|BDBM50159505|AKOS001701120|PD128188

Canonical SMILES:  c1ccc(CN(CCc2c[nH]c3ccccc23)Cc2ccccc2)cc1

Standard InChI:  InChI=1S/C24H24N2/c1-3-9-20(10-4-1)18-26(19-21-11-5-2-6-12-21)16-15-22-17-25-24-14-8-7-13-23(22)24/h1-14,17,25H,15-16,18-19H2

Standard InChI Key:  WEWPMAKQEUSKPV-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA1779158

   1H-Indole-3-ethanamine, N,N-bis(phenylmethyl)-

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 340.47

Molecular Weight (Monoisotopic): 340.1939

AlogP: 5.41

#Rotatable Bonds: 7

Polar Surface Area: 19.03

Molecular Species: BASE

HBA: 1

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa:

CX Basic pKa: 9.46

CX LogP: 5.75

CX LogD: 3.70

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.48

Np Likeness Score: -0.64

References

1. Qu SJ, Wang GF, Duan WH, Yao SY, Zuo JP, Tan CH, Zhu DY..  (2011)  Tryptamine derivatives as novel non-nucleosidic inhibitors against hepatitis B virus.,  19  (10): [PMID:21524588] [10.1016/j.bmc.2011.04.004]

2. Bertamino A, Ostacolo C, Ambrosino P, Musella S, Di Sarno V, Ciaglia T, Soldovieri MV, Iraci N, Fernandez Carvajal A, de la Torre-Martinez R, Ferrer-Montiel A, Gonzalez Muniz R, Novellino E, Taglialatela M, Campiglia P, Gomez-Monterrey I..  (2016)  Tryptamine-Based Derivatives as Transient Receptor Potential Melastatin Type 8 (TRPM8) Channel Modulators.,  59  (5): [PMID:26847872] [10.1021/acs.jmedchem.5b01914]

3. Bertamino A, Iraci N, Ostacolo C, Ambrosino P, Musella S, Di Sarno V, Ciaglia T, Pepe G, Sala M, Soldovieri MV, Mosca I, Gonzalez-Rodriguez S, Fernandez-Carvajal A, Ferrer-Montiel A, Novellino E, Taglialatela M, Campiglia P, Gomez-Monterrey I..  (2018)  Identification of a Potent Tryptophan-Based TRPM8 Antagonist With in Vivo Analgesic Activity.,  61  (14): [PMID:29939028] [10.1021/acs.jmedchem.8b00545]

4. Pérez de Vega MJ, Gómez-Monterrey I, Ferrer-Montiel A, González-Muñiz R..  (2016)  Transient Receptor Potential Melastatin 8 Channel (TRPM8) Modulation: Cool Entryway for Treating Pain and Cancer.,  59  (22): [PMID:27437828] [10.1021/acs.jmedchem.6b00305]

Source

Source(1):

• Scientific Literature