Dimethyl-{2-[3-(1-pyridin-2-yl-ethyl)-1H-inden-2-yl]-ethyl}-amine

ID: ALA564226

Cas Number: 135821-89-5

PubChem CID: 12963076

Max Phase: Preclinical

Molecular Formula: C20H24N2

Molecular Weight: 292.43

Molecule Type: Small molecule

Names and Identifiers

Synonyms: R-Dimethindene | R-dimethindene|Dimetindene, (R)-|(R)-Dimethindene|(-)-Dimethindene|(R)-(-)-Dimethindene|C9Z23T6963|CHEMBL564226|UNII-C9Z23T6963|135821-89-5|1H-Indene-2-ethanamine, N,N-dimethyl-3-((1R)-1-(2-pyridinyl)ethyl)-|1H-Indene-2-ethanamine, N,N-dimethyl-3-(1-(2-pyridinyl)ethyl)-, (R)-|BDBM50297307

Canonical SMILES:  C[C@H](C1=C(CCN(C)C)Cc2ccccc21)c1ccccn1

Standard InChI:  InChI=1S/C20H24N2/c1-15(19-10-6-7-12-21-19)20-17(11-13-22(2)3)14-16-8-4-5-9-18(16)20/h4-10,12,15H,11,13-14H2,1-3H3/t15-/m0/s1

Standard InChI Key:  MVMQESMQSYOVGV-HNNXBMFYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0872    0.0382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8208    1.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3215    1.3677    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9082    2.4146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9352    0.3365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1855   -2.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6552   -2.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3877   -3.5218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1295   -4.3524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5991   -4.6533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5944   -3.5310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1201   -2.1080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6506   -1.8071    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
 10 11  1  0
 11 12  1  0
  2  3  1  0
 12 13  1  0
  3  6  2  0
 12 14  1  0
  1  2  2  0
  7 15  1  0
  5  4  2  0
 15 16  1  0
  6  7  1  0
 15 17  1  6
  7  8  2  0
 16 18  2  0
  8  9  1  0
 18 19  1  0
  9  5  1  0
 19 20  2  0
  4  1  1  0
 20 21  1  0
  8 10  1  0
 21 22  2  0
 22 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA564226

   (S)-(+)-DIMETHINDENE

Molecule Features

Natural Product: Yes

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: 292.43

Molecular Weight (Monoisotopic): 292.1939

AlogP: 4.15

#Rotatable Bonds: 5

Polar Surface Area: 16.13

Molecular Species: BASE

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.70

CX LogP: 3.74

CX LogD: 1.46

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.82

Np Likeness Score: -0.30

References

1. Böhme TM, Keim C, Kreutzmann K, Linder M, Dingermann T, Dannhardt G, Mutschler E, Lambrecht G..  (2003)  Structure-activity relationships of dimethindene derivatives as new M2-selective muscarinic receptor antagonists.,  46  (5): [PMID:12593665] [10.1021/jm020895l]

2. Moree WJ, Li BF, Jovic F, Coon T, Yu J, Gross RS, Tucci F, Marinkovic D, Zamani-Kord S, Malany S, Bradbury MJ, Hernandez LM, O'Brien Z, Wen J, Wang H, Hoare SR, Petroski RE, Sacaan A, Madan A, Crowe PD, Beaton G..  (2009)  Characterization of novel selective H1-antihistamines for clinical evaluation in the treatment of insomnia.,  52  (17): [PMID:19663387] [10.1021/jm900933k]

3. Moree WJ, Li BF, Zamani-Kord S, Yu J, Coon T, Huang C, Marinkovic D, Tucci FC, Malany S, Bradbury MJ, Hernandez LM, Wen J, Wang H, Hoare SR, Petroski RE, Jalali K, Yang C, Sacaan A, Madan A, Crowe PD, Beaton G..  (2010)  Identification of a novel selective H1-antihistamine with optimized pharmacokinetic properties for clinical evaluation in the treatment of insomnia.,  20  (19): [PMID:20800486] [10.1016/j.bmcl.2010.07.117]

4. Honda H, Tomizawa M, Casida JE..  (2007)  Insect muscarinic acetylcholine receptor: pharmacological and toxicological profiles of antagonists and agonists.,  55  (6): [PMID:17319687] [10.1021/jf0631934]

Source

Source(1):

• Scientific Literature