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Showing NP-Card for 4-Methylphenethylamine (NP0045111)

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Record Information
Version2.0
Created at2022-03-10 18:58:10 UTC
Updated at2022-03-10 22:17:30 UTC
NP-MRD IDNP0045111
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Methylphenethylamine
Description4-Methylphenethylamine also known as para-methylphenethylamine, with the chemical formula of C9H13N, belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine. 4-Methylphenethylamine is a very strong basic compound (based on its pKa). As its monomethylated isomers, alpha-methylphenethylamine, beta-methylphenethylamine, and N-methylphenethylamine, 4-methylphenethylamine is an agonist of the trace amine associated receptor 1 (TAAR1) in humans (PMID: 17038507 ). Furthermore, there is also evidence showing that 4-methylphenethylamine might inhibit the cytochrome P450 CYP1A2 and CYP2A6 enzymes, in humans. 4-Methylphenetylamine has been detected as a volatile component in Marijuana samples obtained in police seizures (PMID:26657499 ).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0045111 (4-Methylphenethylamine)


  Mrv1652303192001423D          

 10 10  0  0  0  0            999 V2000
    3.7684   -0.4643    0.2320 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4636   -1.4148    0.1742 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7706    0.8986   -0.2981 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0861   -1.2539   -0.0203 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3920    1.0272   -0.4857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8866    0.1307   -0.5522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4927    0.4944    0.8013 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3034   -0.3302    0.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4430   -0.0415   -0.3476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9019    0.6916    0.7453 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  2  4  2  0  0  0  0
  2  8  1  0  0  0  0
  3  5  1  0  0  0  0
  3  8  2  0  0  0  0
  4  9  1  0  0  0  0
  5  9  2  0  0  0  0
  6  7  1  0  0  0  0
  6  9  1  0  0  0  0
  7 10  1  0  0  0  0
M  END
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3D MOL for NP0045111 (4-Methylphenethylamine)

     RDKit          3D

 23 23  0  0  0  0  0  0  0  0999 V2000
    3.8344   -0.4271    0.0740 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3649   -0.1423    0.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7566    0.5402   -0.8880 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3950    0.7977   -0.8275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3696    0.3781    0.2426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8026    0.6891    0.2330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6370   -0.3943   -0.4290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0173    0.0683   -0.3537 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2590   -0.3121    1.2636 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6186   -0.5704    1.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3990    0.2042    0.8005 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2150   -0.2431   -0.9522 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9871   -1.5263    0.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3063    0.8957   -1.7562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0816    1.3431   -1.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2237    0.7892    1.2761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9703    1.6213   -0.3479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5680   -1.3161    0.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3204   -0.6336   -1.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6924   -0.7176   -0.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2113    0.7083   -1.1536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3502   -0.6392    2.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1083   -1.1130    2.0096 H   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  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  5  9  1  0
  9 10  2  0
 10  2  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  4 15  1  0
  6 16  1  0
  6 17  1  0
  7 18  1  0
  7 19  1  0
  8 20  1  0
  8 21  1  0
  9 22  1  0
 10 23  1  0
M  END
Download

3D SDF for NP0045111 (4-Methylphenethylamine)


  Mrv1652303192001423D          

 10 10  0  0  0  0            999 V2000
    3.7684   -0.4643    0.2320 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4636   -1.4148    0.1742 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7706    0.8986   -0.2981 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0861   -1.2539   -0.0203 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3920    1.0272   -0.4857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8866    0.1307   -0.5522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4927    0.4944    0.8013 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3034   -0.3302    0.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4430   -0.0415   -0.3476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9019    0.6916    0.7453 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  2  4  2  0  0  0  0
  2  8  1  0  0  0  0
  3  5  1  0  0  0  0
  3  8  2  0  0  0  0
  4  9  1  0  0  0  0
  5  9  2  0  0  0  0
  6  7  1  0  0  0  0
  6  9  1  0  0  0  0
  7 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045111

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC=C(CCN)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H13N/c1-8-2-4-9(5-3-8)6-7-10/h2-5H,6-7,10H2,1H3

> <INCHI_KEY>
VKJXAQYPOTYDLO-UHFFFAOYSA-N

> <FORMULA>
C9H13N

> <MOLECULAR_WEIGHT>
135.21

> <EXACT_MASS>
135.104799423

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
16.537360362720857

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(4-methylphenyl)ethan-1-amine

> <ALOGPS_LOGP>
1.67

> <JCHEM_LOGP>
1.9010968463333329

> <ALOGPS_LOGS>
-1.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.813351807493081

> <JCHEM_POLAR_SURFACE_AREA>
26.02

> <JCHEM_REFRACTIVITY>
44.327600000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.65e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
benzeneethanamine, 4-methyl-

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0045111 (4-Methylphenethylamine)

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PDB for NP0045111 (4-Methylphenethylamine)
HEADER    PROTEIN                                 19-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-MAR-20         0                                  
HETATM    1  C   UNK     0       3.768  -0.464   0.232  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.464  -1.415   0.174  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.771   0.899  -0.298  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.086  -1.254  -0.020  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.392   1.027  -0.486  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.887   0.131  -0.552  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.493   0.494   0.801  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.303  -0.330   0.033  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.443  -0.042  -0.348  0.00  0.00           C+0
HETATM   10  N   UNK     0      -3.902   0.692   0.745  0.00  0.00           N+0
CONECT    1    8                                                            
CONECT    2    4    8                                                       
CONECT    3    5    8                                                       
CONECT    4    2    9                                                       
CONECT    5    3    9                                                       
CONECT    6    7    9                                                       
CONECT    7    6   10                                                       
CONECT    8    1    2    3                                                  
CONECT    9    4    5    6                                                  
CONECT   10    7                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END

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3D PDB for NP0045111 (4-Methylphenethylamine)
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SMILES for NP0045111 (4-Methylphenethylamine)
CC1=CC=C(CCN)C=C1
Download
INCHI for NP0045111 (4-Methylphenethylamine)
InChI=1S/C9H13N/c1-8-2-4-9(5-3-8)6-7-10/h2-5H,6-7,10H2,1H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC9H13N
Average Mass135.2100 Da
Monoisotopic Mass135.10480 Da
IUPAC Name2-(4-methylphenyl)ethan-1-amine
Traditional Namebenzeneethanamine, 4-methyl-
CAS Registry Number3261-62-9
SMILES
CC1=CC=C(CCN)C=C1
InChI Identifier
InChI=1S/C9H13N/c1-8-2-4-9(5-3-8)6-7-10/h2-5H,6-7,10H2,1H3
InChI KeyVKJXAQYPOTYDLO-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cannabis sativaNULL
      Not Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassPhenethylamines  
Direct ParentPhenethylamines  
Alternative Parents
Substituents
  • Phenethylamine
    • 

  • 2-arylethylamine
    • 

  • Aralkylamine
    • 

  • Toluene
    • 

  • Organic nitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Primary amine
    • 

  • Organonitrogen compound
    • 

  • Primary aliphatic amine
    • 

  • Amine
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.67ALOGPS
logP1.9ChemAxon
logS-1.9ALOGPS
pKa (Strongest Basic)9.81ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.02 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.33 m³·mol⁻¹ChemAxon
Polarizability16.54 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link4-Methylphenethylamine  
METLIN IDNot Available
PubChem Compound76751  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References