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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:00 UTC
HMDB IDHMDB0015519
Secondary Accession Numbers
  • HMDB15519
Metabolite Identification
Common NamePhendimetrazine
DescriptionPhendimetrazine, also known as hyrex or di-ap-trol, 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. Based on a literature review very few articles have been published on Phendimetrazine.
Structure
Data?1582753305
Synonyms
ValueSource
(+)-3,4-Dimethyl-2-phenylmorpholineHMDB
(+)-PhendimetrazineHMDB
(2S,3S)-3,4-Dimethyl-2-phenylmorpholineHMDB
3,4-Dimethyl-2-phenylmorpholineHMDB
3-Phenyl-2-methylmorpholineHMDB
D-2-Phenyl-3,4-dimethylmorpholineHMDB
HyrexHMDB
Phendimetrazine tartrateHMDB
Di-ap-trolHMDB
Prelu-2HMDB
TrimstatHMDB
WeightrolHMDB
Phendimetrazine hydrochlorideHMDB
Phendimetrazine hydrochloride, (2S-trans)-isomerHMDB
Phendimetrazine, (2R-cis)-isomerHMDB
ObezineHMDB
Phendimetrazine tartrate, (R-(r*,r*))-isomerHMDB
Phendimetrazine, (2S-trans)-isomerHMDB
DyrexanHMDB
MelfiatHMDB
X-TrozineHMDB
Phendimetrazine tartrate, (2S-trans(R-(r*,r*)))-isomerHMDB
Phendimetrazine, trans(+-)-isomerHMDB
AdipostHMDB
WehlessHMDB
BontrilHMDB
PhendimetrazineMeSH
Chemical FormulaC12H17NO
Average Molecular Weight191.2695
Monoisotopic Molecular Weight191.131014171
IUPAC Name3,4-dimethyl-2-phenylmorpholine
Traditional Namephendimetrazine
CAS Registry Number634-03-7
SMILES
CC1C(OCCN1C)C1=CC=CC=C1
InChI Identifier
InChI=1S/C12H17NO/c1-10-12(14-9-8-13(10)2)11-6-4-3-5-7-11/h3-7,10,12H,8-9H2,1-2H3
InChI KeyMFOCDFTXLCYLKU-UHFFFAOYSA-N
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
  • Tertiary amine
  • Tertiary aliphatic amine
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Azacycle
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point134.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.43 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.43 g/LALOGPS
logP2.01ALOGPS
logP2.17ChemAxon
logS-1.9ALOGPS
pKa (Strongest Basic)7.28ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.47 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity57.76 m³·mol⁻¹ChemAxon
Polarizability21.99 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+144.19631661259
DarkChem[M-H]-139.75231661259
DeepCCS[M+H]+139.6130932474
DeepCCS[M-H]-136.32730932474
DeepCCS[M-2H]-173.26430932474
DeepCCS[M+Na]+148.80330932474
AllCCS[M+H]+142.532859911
AllCCS[M+H-H2O]+138.132859911
AllCCS[M+NH4]+146.632859911
AllCCS[M+Na]+147.832859911
AllCCS[M-H]-148.032859911
AllCCS[M+Na-2H]-148.532859911
AllCCS[M+HCOO]-149.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PhendimetrazineCC1C(OCCN1C)C1=CC=CC=C12036.1Standard polar33892256
PhendimetrazineCC1C(OCCN1C)C1=CC=CC=C11423.2Standard non polar33892256
PhendimetrazineCC1C(OCCN1C)C1=CC=CC=C11484.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Phendimetrazine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00r6-8900000000-d4db6599fc2e135c0bf42017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phendimetrazine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Phendimetrazine 35V, Positive-QTOFsplash10-0007-0900000000-9b323309453c1521a2372021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phendimetrazine 10V, Positive-QTOFsplash10-0006-0900000000-63fefd084876108da6ba2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phendimetrazine 20V, Positive-QTOFsplash10-00kf-1900000000-94f03e3354008fb370c52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phendimetrazine 40V, Positive-QTOFsplash10-0a5c-9200000000-7f4d324e8e208a6717f92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phendimetrazine 10V, Negative-QTOFsplash10-0006-1900000000-159dbd9bfb6baa619c872016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phendimetrazine 20V, Negative-QTOFsplash10-0006-4900000000-8c771afc7395bd5a28502016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phendimetrazine 40V, Negative-QTOFsplash10-0a4i-7900000000-3279b0122cfa44f770432016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phendimetrazine 10V, Positive-QTOFsplash10-0006-0900000000-c75934d65ac8f9ba6edc2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phendimetrazine 20V, Positive-QTOFsplash10-0006-5900000000-6a91a53820e288e0b63d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phendimetrazine 40V, Positive-QTOFsplash10-0006-9200000000-cce47b5d798496f23e272021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phendimetrazine 10V, Negative-QTOFsplash10-0006-1900000000-3a3d902120b3533a455a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phendimetrazine 20V, Negative-QTOFsplash10-0007-8900000000-93c57fadbb7560fb052e2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phendimetrazine 40V, Negative-QTOFsplash10-004i-9400000000-8d57751192677c87a9112021-10-11Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01579 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01579 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID11950
KEGG Compound IDC07904
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhendimetrazine
METLIN IDNot Available
PubChem Compound12460
PDB IDNot Available
ChEBI ID674499
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
Gene Name:
ADRA1A
Uniprot ID:
P35348
Molecular weight:
51486.0
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Bray GA: Drug Insight: appetite suppressants. Nat Clin Pract Gastroenterol Hepatol. 2005 Feb;2(2):89-95. [PubMed:16265126 ]
  4. Bray GA: A concise review on the therapeutics of obesity. Nutrition. 2000 Oct;16(10):953-60. [PubMed:11054601 ]
  5. Rothman RB, Baumann MH: Therapeutic potential of monoamine transporter substrates. Curr Top Med Chem. 2006;6(17):1845-59. [PubMed:17017961 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system
Gene Name:
ADRA1B
Uniprot ID:
P35368
Molecular weight:
56835.4
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Bray GA: Drug Insight: appetite suppressants. Nat Clin Pract Gastroenterol Hepatol. 2005 Feb;2(2):89-95. [PubMed:16265126 ]
  4. Bray GA: A concise review on the therapeutics of obesity. Nutrition. 2000 Oct;16(10):953-60. [PubMed:11054601 ]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  6. Rothman RB, Baumann MH: Therapeutic potential of monoamine transporter substrates. Curr Top Med Chem. 2006;6(17):1845-59. [PubMed:17017961 ]

Transporters

General function:
Involved in neurotransmitter:sodium symporter activity
Specific function:
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:
SLC6A2
Uniprot ID:
P23975
Molecular weight:
69331.42
References
  1. Rothman RB, Baumann MH: Therapeutic potential of monoamine transporter substrates. Curr Top Med Chem. 2006;6(17):1845-59. [PubMed:17017961 ]