2-[2-Methoxy-5-(3-phenyl-propyl)-phenyl]-1-methyl-ethylamine

ID: ALA113215

PubChem CID: 9882247

Max Phase: Preclinical

Molecular Formula: C19H25NO

Molecular Weight: 283.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(CCCc2ccccc2)cc1CC(C)N

Standard InChI:  InChI=1S/C19H25NO/c1-15(20)13-18-14-17(11-12-19(18)21-2)10-6-9-16-7-4-3-5-8-16/h3-5,7-8,11-12,14-15H,6,9-10,13,20H2,1-2H3

Standard InChI Key:  QVJYLZMOZOXXCB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
    3.3250   -2.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6125   -2.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0417   -2.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3167   -1.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6125   -3.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0417   -3.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3250   -3.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0292   -0.2667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9000   -2.3375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0375   -1.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4750   -6.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7542   -4.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7542   -3.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4750   -5.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1792   -2.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7625   -6.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1917   -6.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7500   -1.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7667   -7.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1917   -7.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4792   -7.6917    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  2  2  0
  6  3  1  0
  7  6  2  0
  8 10  1  0
  9  2  1  0
 10  4  1  0
 11 14  1  0
 12 13  1  0
 13  6  1  0
 14 12  1  0
 15  9  1  0
 16 11  2  0
 17 11  1  0
 18 10  1  0
 19 16  1  0
 20 17  2  0
 21 20  1  0
  5  7  1  0
 19 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA113215

   2-[2-Methoxy-5-(3-phenyl-propyl)-phenyl]-1-methyl-ethylamine

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: 283.42

Molecular Weight (Monoisotopic): 283.1936

AlogP: 3.76

#Rotatable Bonds: 7

Polar Surface Area: 35.25

Molecular Species: BASE

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.94

CX LogP: 4.63

CX LogD: 2.21

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.84

Np Likeness Score: 0.10

References

1. Rangisetty JB, Dukat M, Dowd CS, Herrick-Davis K, DuPre A, Gadepalli S, Teitler M, Kelley CR, Sharif NA, Glennon RA..  (2001)  1-[2-methoxy-5-(3-phenylpropyl)]-2-aminopropane unexpectedly shows 5-HT(2A) serotonin receptor affinity and antagonist character.,  44  (20): [PMID:11563927] [10.1021/jm0100739]

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