2-(5-Methoxy-1H-indol-1-yl)-N,N-dimethylethan-1-amine Fumarate Salt

ID: ALA4465234

PubChem CID: 155530886

Max Phase: Preclinical

Molecular Formula: C17H22N2O5

Molecular Weight: 218.30

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc2c(ccn2CCN(C)C)c1.O=C(O)/C=C/C(=O)O

Standard InChI:  InChI=1S/C13H18N2O.C4H4O4/c1-14(2)8-9-15-7-6-11-10-12(16-3)4-5-13(11)15;5-3(6)1-2-4(7)8/h4-7,10H,8-9H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;2-1+

Standard InChI Key:  WZRWXJXOKZKSKT-WLHGVMLRSA-N

Molfile:  

     RDKit          2D

 24 24  0  0  0  0  0  0  0  0999 V2000
   15.1101  -21.6234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8246  -21.2109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5390  -21.6234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2535  -21.2109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9680  -21.6234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2535  -20.3859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3956  -21.2109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1101  -22.4484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8903  -19.3751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8891  -20.2024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6040  -20.6154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6022  -18.9623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3176  -19.3715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3178  -20.2025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1083  -20.4591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5966  -19.7866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1078  -19.1144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3626  -18.3298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1695  -18.1580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7217  -18.7709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5286  -18.5991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4670  -19.5556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1744  -20.6143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4602  -20.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  1  7  1  0
  1  8  2  0
  9 10  2  0
 10 11  1  0
 11 14  2  0
 13 12  2  0
 12  9  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 13  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 10 23  1  0
 23 24  1  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 218.30

Molecular Weight (Monoisotopic): 218.1419

AlogP: 2.21

#Rotatable Bonds: 4

Polar Surface Area: 17.40

Molecular Species: BASE

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.24

CX LogP: 2.16

CX LogD: 0.32

Aromatic Rings: 2

Heavy Atoms: 16

QED Weighted: 0.78

Np Likeness Score: -1.41

References

1. Dunlap LE, Azinfar A, Ly C, Cameron LP, Viswanathan J, Tombari RJ, Myers-Turnbull D, Taylor JC, Grodzki AC, Lein PJ, Kokel D, Olson DE..  (2020)  Identification of Psychoplastogenic N,N-Dimethylaminoisotryptamine (isoDMT) Analogues through Structure-Activity Relationship Studies.,  63  (3): [PMID:31977208] [10.1021/acs.jmedchem.9b01404]

Source

Source(1):

• Scientific Literature