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Showing NP-Card for phenmetrazine (NP0172418)

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Record Information
Version2.0
Created at2022-09-03 09:20:24 UTC
Updated at2022-09-03 09:20:24 UTC
NP-MRD IDNP0172418
Secondary Accession NumbersNone
Natural Product Identification
Common Namephenmetrazine
DescriptionPhenmetrazine, also known as oxazimedrine or usaf ge-1, belongs to the class of organic compounds known as phenylmorpholines. These are aromatic compounds containing a morpholine ring and a benzene ring linked to each other through a CC or a CN bond. Phenmetrazine is a drug which is used as an anorectic in the treatment of obesity. Preludin was also used recreationally in the US throughout the 1960s and early 1970s. In a study of the effectiveness on weight loss between phenmetrazine and dextroamphetamine, phenmetrazine was found to be slightly more effective. Phenmetrazine is a very strong basic compound (based on its pKa). Phenmetrazine is a potentially toxic compound. phenmetrazine was first documented in 1964 (PMID: 14196928). In clinical use, phenmetrazine produces less nervousness, hyperexcitability, euphoria and insomnia than drugs of the amphetamine family (PMID: 23211394) (PMID: 4125018) (PMID: 5356063).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0172418 (phenmetrazine)

830
  Mrv0541 02231215022D          

 13 14  0  0  1  0            999 V2000
    4.5080    0.4620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.1880    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2  5  1  0  0  0  0
  3  4  1  0  0  0  0
  3  8  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  7  9  2  0  0  0  0
  7 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  2  0  0  0  0
 11 13  2  0  0  0  0
 12 13  1  0  0  0  0
M  END
Download

3D MOL for NP0172418 (phenmetrazine)

     RDKit          3D

 28 29  0  0  0  0  0  0  0  0999 V2000
   -1.4055   -1.7292    0.1221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1213   -0.4522    0.8619 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4314    0.1997    1.0399 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9588    0.6196   -0.2357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9796    1.4949   -0.9681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8227    0.7328   -1.1795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2715    0.5200    0.1033 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1522    0.2051    0.0605 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6236   -0.7047   -0.8610 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9620   -1.0469   -0.9533 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8701   -0.4838   -0.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4378    0.4324    0.8172 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0965    0.7614    0.8939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4702   -1.5728   -0.9787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6745   -2.5279    0.3902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3993   -2.1464    0.4094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6867   -0.6371    1.8443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3653    1.0109    1.6716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2289   -0.2199   -0.8908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8590    1.2418   -0.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7920    2.3820   -0.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3946    1.7651   -1.9573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3872    1.5060    0.6222 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9593   -1.1754   -1.5367 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2783   -1.7660   -1.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9282   -0.7648   -0.2048 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1549    0.8765    1.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7855    1.4789    1.6340 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  7  2  1  0
 13  8  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  1
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  7 23  1  1
  9 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
M  END
Download

3D SDF for NP0172418 (phenmetrazine)

830
  Mrv0541 02231215022D          

 13 14  0  0  1  0            999 V2000
    4.5080    0.4620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.1880    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2  5  1  0  0  0  0
  3  4  1  0  0  0  0
  3  8  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  7  9  2  0  0  0  0
  7 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  2  0  0  0  0
 11 13  2  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0172418

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1NCCOC1C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H15NO/c1-9-11(13-8-7-12-9)10-5-3-2-4-6-10/h2-6,9,11-12H,7-8H2,1H3

> <INCHI_KEY>
OOBHFESNSZDWIU-UHFFFAOYSA-N

> <FORMULA>
C11H15NO

> <MOLECULAR_WEIGHT>
177.2429

> <EXACT_MASS>
177.115364107

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
20.09805902270938

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-methyl-2-phenylmorpholine

> <ALOGPS_LOGP>
1.45

> <JCHEM_LOGP>
1.7894362886666664

> <ALOGPS_LOGS>
-1.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.222129279868874

> <JCHEM_POLAR_SURFACE_AREA>
21.259999999999998

> <JCHEM_REFRACTIVITY>
52.46950000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.44e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenmetrazine

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0172418 (phenmetrazine)

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PDB for NP0172418 (phenmetrazine)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 830                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       8.415   0.862   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       8.415  -2.218   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       7.081  -1.448   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.081   0.092   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.748  -1.448   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.748   0.092   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.748   0.862   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.748  -2.218   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414   0.092   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.748   2.402   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.080   0.862   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414   3.172   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.080   2.402   0.000  0.00  0.00           C+0
CONECT    1    4    6                                                       
CONECT    2    3    5                                                       
CONECT    3    2    4    8                                                  
CONECT    4    1    3    7                                                  
CONECT    5    2    6                                                       
CONECT    6    1    5                                                       
CONECT    7    4    9   10                                                  
CONECT    8    3                                                            
CONECT    9    7   11                                                       
CONECT   10    7   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   13                                                       
CONECT   13   11   12                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

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3D PDB for NP0172418 (phenmetrazine)
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SMILES for NP0172418 (phenmetrazine)
CC1NCCOC1C1=CC=CC=C1
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INCHI for NP0172418 (phenmetrazine)
InChI=1S/C11H15NO/c1-9-11(13-8-7-12-9)10-5-3-2-4-6-10/h2-6,9,11-12H,7-8H2,1H3
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View in JSmol
Synonyms
ValueSource
2-Phenyl-3-methylmorpholineChEBI
3-Methyl-2-phenylmorpholineHMDB
DefenmetrazinHMDB
DexphenmetrazineHMDB
FenmetrazinHMDB
OxazimedrineHMDB
USAF ge-1HMDB
Hydrochloride, phenmetrazineHMDB
PhenmetralineHMDB
Phenmetrazine hydrochlorideHMDB
PreludinHMDB
Chemical FormulaC11H15NO
Average Mass177.2429 Da
Monoisotopic Mass177.11536 Da
IUPAC Name3-methyl-2-phenylmorpholine
Traditional Namephenmetrazine
CAS Registry NumberNot Available
SMILES
CC1NCCOC1C1=CC=CC=C1
InChI Identifier
InChI=1S/C11H15NO/c1-9-11(13-8-7-12-9)10-5-3-2-4-6-10/h2-6,9,11-12H,7-8H2,1H3
InChI KeyOOBHFESNSZDWIU-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylmorpholines. These are aromatic compounds containing a morpholine ring and a benzene ring linked to each other through a CC or a CN bond.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassOxazinanes  
Sub ClassMorpholines  
Direct ParentPhenylmorpholines  
Alternative Parents
Substituents
  • Phenylmorpholine
    • 

  • Aralkylamine
    • 

  • Monocyclic benzene moiety
    • 

  • Benzenoid
    • 

  • Dialkyl ether
    • 

  • Secondary aliphatic amine
    • 

  • Ether
    • 

  • Secondary amine
    • 

  • Azacycle
    • 

  • Oxacycle
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Amine
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic nitrogen compound
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
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
logP1.45ALOGPS
logP1.79ChemAxon
logS-1.9ALOGPS
pKa (Strongest Basic)8.22ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area21.26 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity52.47 m³·mol⁻¹ChemAxon
Polarizability20.1 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0014968  
DrugBank IDDB00830  
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4598  
KEGG Compound IDC07432  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhenmetrazine  
METLIN IDNot Available
PubChem Compound4762  
PDB IDNot Available
ChEBI ID8067  
Good Scents IDNot Available
References
General References
  1. BALAZ V: GLUCOTROPIC ACTION OF PHENMETRAZINE. Fed Proc Transl Suppl. 1964 Jul-Aug;23:769-71. [PubMed:14196928  ] 
  2. Banks ML, Blough BE, Fennell TR, Snyder RW, Negus SS: Role of phenmetrazine as an active metabolite of phendimetrazine: evidence from studies of drug discrimination and pharmacokinetics in rhesus monkeys. Drug Alcohol Depend. 2013 Jun 1;130(1-3):158-66. doi: 10.1016/j.drugalcdep.2012.10.026. Epub 2012 Dec 1. [PubMed:23211394  ] 
  3. Aloia JF: Phenmetrazine in diabetes insipidus. Lancet. 1973 Sep 1;2(7827):501-2. doi: 10.1016/s0140-6736(73)92099-0. [PubMed:4125018  ] 
  4. Negulici-Baliff E, Christodorescu D, Gheorghiu D: [Psychoses induced by phenmetrazine]. Neurol Psihiatr Neurochir. 1969 Jul-Aug;14(4):371-6. [PubMed:5356063  ] 
  5. LOTUS database [Link]