2-(1H-Indol-3-yl)-1-methyl-ethylamine

ID: ALA2093087

Cas Number: 7795-51-9

PubChem CID: 854157

Max Phase: Preclinical

Molecular Formula: C11H14N2

Molecular Weight: 174.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](N)Cc1c[nH]c2ccccc12

Standard 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/t8-/m0/s1

Standard InChI Key:  QSQQQURBVYWZKJ-QMMMGPOBSA-N

Molfile:  

     RDKit          2D

 13 14  0  0  0  0  0  0  0  0999 V2000
    4.6740   -6.1919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6798   -7.5323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1609   -6.8621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8893   -6.4669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9065   -7.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6626   -5.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3671   -4.1299    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3671   -4.9547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1848   -6.0545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1848   -7.7041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0888   -5.3613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4745   -6.4783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4802   -7.3031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  1  2  0
  4  1  1  0
  5  4  2  0
  6  1  1  0
  7  8  1  0
  8  6  1  0
  9  4  1  0
 10  5  1  0
  8 11  1  1
 12  9  2  0
 13 12  1  0
  2  5  1  0
 10 13  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2093087

   1H-Indole-3-ethanamine, alpha-methyl-, (alphaS)-

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: 174.25

Molecular Weight (Monoisotopic): 174.1157

AlogP: 2.06

#Rotatable Bonds: 2

Polar Surface Area: 41.81

Molecular Species: BASE

HBA: 1

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.96

CX LogP: 1.90

CX LogD: -0.53

Aromatic Rings: 2

Heavy Atoms: 13

QED Weighted: 0.72

Np Likeness Score: -0.09

References

1. Nichols DE, Lloyd DH, Johnson MP, Hoffman AJ..  (1988)  Synthesis and serotonin receptor affinities of a series of enantiomers of alpha-methyltryptamines: evidence for the binding conformation of tryptamines at serotonin 5-HT1B receptors.,  31  (7): [PMID:3385733] [10.1021/jm00402a026]

2. Glennon RA..  (2017)  The 2014 Philip S. Portoghese Medicinal Chemistry Lectureship: The "Phenylalkylaminome" with a Focus on Selected Drugs of Abuse.,  60  (7): [PMID:28244748] [10.1021/acs.jmedchem.7b00085]

Source

Source(1):

• Scientific Literature