2-(2,5-Dimethoxy-phenyl)-ethylamine

ID: ALA287047

Cas Number: 3600-86-0

PubChem CID: 76632

Product Number: W134633, Order Now?

Max Phase: Preclinical

Molecular Formula: C10H15NO2

Molecular Weight: 181.24

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 2-(2,5-Dimethoxyphenyl)Ethylamine | 2,5-Dimethoxyphenethylamine|3600-86-0|2-(2,5-Dimethoxyphenyl)ethanamine|2-(2,5-Dimethoxy-phenyl)-ethylamine|2-(2,5-Dimethoxyphenyl)Ethylamine|2C-H|9A8XF4GA0X|CHEMBL287047|NSC-168525|benzeneethanamine, 2,5-dimethoxy-|UNII-9A8XF4GA0X|2,5-Dimethoxyphenethyl amine|SCHEMBL479514|DEA No. 7517|(2,5-Dimethoxyphenyl)ethylamine|DTXSID80189564|CHEBI:125507|2,5-Dimethoxyphenethylamine, 97%|BCP10409|BDBM50026778|MFCD00060614|NSC168525|2-(2,5-Dimethoxyphenyl)ethanamine #|AKShow More⌵

Canonical SMILES:  COc1ccc(OC)c(CCN)c1

Standard InChI:  InChI=1S/C10H15NO2/c1-12-9-3-4-10(13-2)8(7-9)5-6-11/h3-4,7H,5-6,11H2,1-2H3

Standard InChI Key:  WNCUVUUEJZEATP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 13 13  0  0  0  0  0  0  0  0999 V2000
   15.3793  -10.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3780  -10.8737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0910  -11.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8102  -10.8732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8071  -10.0422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0890   -9.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5195   -9.6261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2360  -10.0350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9484   -9.6190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5251  -11.2850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5258  -12.1099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6646   -9.6342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6638   -8.8092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  5  7  1  0
  3  4  2  0
  7  8  1  0
  8  9  1  0
  4  5  1  0
  4 10  1  0
  2  3  1  0
 10 11  1  0
  5  6  2  0
  1 12  1  0
  6  1  1  0
 12 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA287047

   2,5-Dimethoxyphenethylamine

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: 181.24

Molecular Weight (Monoisotopic): 181.1103

AlogP: 1.20

#Rotatable Bonds: 4

Polar Surface Area: 44.48

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.68

CX LogP: 1.07

CX LogD: -1.14

Aromatic Rings: 1

Heavy Atoms: 13

QED Weighted: 0.76

Np Likeness Score: 0.05

References

1. DeMarinis RM, Bryan WM, Shah DH, Hieble JP, Pendleton RG..  (1981)  Alpha-adrenergic agents. 1. Direct-acting alpha 1 agonists related to methoxamine.,  24  (12): [PMID:6118438] [10.1021/jm00144a012]

2. Glennon RA, Liebowitz SM, Anderson GM..  (1980)  Serotonin receptor affinities of psychoactive phenalkylamine analogues.,  23  (3): [PMID:7365744] [10.1021/jm00177a017]

3. Dowd CS, Herrick-Davis K, Egan C, DuPre A, Smith C, Teitler M, Glennon RA..  (2000)  1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT(2A) partial agonists.,  43  (16): [PMID:10956215] [10.1021/jm9906062]

4. 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]

5. Lewin AH, Navarro HA, Mascarella SW..  (2008)  Structure-activity correlations for beta-phenethylamines at human trace amine receptor 1.,  16  (15): [PMID:18602830] [10.1016/j.bmc.2008.06.009]

6. Glennon RA, Liebowitz SM, Mack EC..  (1978)  Serotonin receptor binding affinities of several hallucinogenic phenylalkylamine and N,N-dimethyltryptamine analogues.,  21  (8): [PMID:278843] [10.1021/jm00206a022]

7. 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]

8. Johannes Zuegg, Alysha Elliott, Maite Amado, Emma Cowie, Ali Hinton, Geraldine Kaeslin, Angela Kavanagh, Anne Kunert, Gabriell Lowe, Soumya Ramu, Janet Reid, Robin Trauer, Mathilde Desselle, Ruth Neale, Karl Hansford, Mark Blascovich, Matthew Cooper. CO-ADD screening of MMV (CH) - Small Polar Library,  [10.6019/CHEMBL4513160]

9. University of Dundee.  (2021)  University of Dundee, Small-Polar-MMV Screening Library,  [10.6019/CHEMBL3988442]

Source

Source(3):

• Scientific Literature
• Gates Library compound collection
• CO-ADD antimicrobial screening data