(-)2-(2,5-Dimethoxy-4-nitro-phenyl)-1-methyl-ethylamine

ID: ALA1788278

Cas Number: 64778-74-1

PubChem CID: 54580952

Max Phase: Preclinical

Molecular Formula: C11H16N2O4

Molecular Weight: 240.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc([N+](=O)[O-])c(OC)cc1C[C@@H](C)N

Standard InChI:  InChI=1S/C11H16N2O4/c1-7(12)4-8-5-11(17-3)9(13(14)15)6-10(8)16-2/h5-7H,4,12H2,1-3H3/t7-/m1/s1

Standard InChI Key:  JQJRESSXOVAECC-SSDOTTSWSA-N

Molfile:  

     RDKit          2D

 17 17  0  0  0  0  0  0  0  0999 V2000
    6.8578   -5.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8464   -6.7031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1417   -5.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5683   -5.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8578   -4.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1417   -4.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5683   -4.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1417   -7.1156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5683   -7.1156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8636   -3.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2730   -5.8667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4313   -4.2109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5797   -2.1542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5797   -2.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9948   -5.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7151   -4.6234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2901   -3.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  1  1  0
  5  7  1  0
  6  3  1  0
  7  4  2  0
  8  2  1  0
  9  2  2  0
 10  5  1  0
 11  4  1  0
 12  6  1  0
 14 13  1  6
 14 10  1  0
 15 11  1  0
 16 12  1  0
 17 14  1  0
  6  5  2  0
M  CHG  2   2   1   8  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1788278

   Benzeneethanamine, 2,5-dimethoxy-alpha-methyl-4-nitro-, (alphaR)-

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: 240.26

Molecular Weight (Monoisotopic): 240.1110

AlogP: 1.50

#Rotatable Bonds: 5

Polar Surface Area: 87.62

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.82

CX LogP: 1.43

CX LogD: -0.90

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.62

Np Likeness Score: -0.47

References

1. Glennon RA, Young R, Benington F, Morin RD..  (1982)  Behavioral and serotonin receptor properties of 4-substituted derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane.,  25  (10): [PMID:7143352] [10.1021/jm00352a013]

2. Glennon RA..  (1987)  Central serotonin receptors as targets for drug research.,  30  (1): [PMID:3543362] [10.1021/jm00384a001]

Source

Source(1):

• Scientific Literature