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Phendimetrazine

July 24, 2017
Common Name

Phendimetrazine Description

Phendimetrazine is a weight loss medication. Phendimetrazine is chemically related to amphetamines and is a Schedlie III drug under the Convention on Psychotropic Substances. In the United States, phendimetrazine is a Schedlie III controlled substance under the Uniform Controlled Substances Act of 1970. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source (+)-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 HyrexMeSH Phendimetrazine tartrateMeSH Di-ap-trolMeSH Prelu-2MeSH TrimstatMeSH WeightrolMeSH Phendimetrazine hydrochlorideMeSH Phendimetrazine hydrochloride, (2S-trans)-isomerMeSH Phendimetrazine, (2R-cis)-isomerMeSH ObezineMeSH Phendimetrazine tartrate, (R-(r*,r*))-isomerMeSH Phendimetrazine, (2S-trans)-isomerMeSH DyrexanMeSH MelfiatMeSH X-TrozineMeSH Phendimetrazine tartrate, (2S-trans(R-(r*,r*)))-isomerMeSH Phendimetrazine, trans(+-)-isomerMeSH AdipostMeSH WehlessMeSH

Chemical Formlia

C12H17NO Average Molecliar Weight

191.2695 Monoisotopic Molecliar Weight

191.131014171 IUPAC Name

3,4-dimethyl-2-phenylmorpholine Traditional Name

phendimetrazine CAS Registry Number

634-03-7 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 Key

MFOCDFTXLCYLKU-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities 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. Kingdom

Chemical entities Super Class

Organic compounds Class

Organoheterocyclic compounds Sub Class

Oxazinanes Direct Parent

Phenylmorpholines Alternative Parents

  • Aralkylamines
  • Benzene and substituted derivatives
  • Trialkylamines
  • Oxacyclic compounds
  • Dialkyl ethers
  • Azacyclic compounds
  • Organopnictogen compounds
  • Hydrocarbon derivatives

    • 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

    • Molecliar Framework

    Aromatic heteromonocyclic compounds External Descriptors

    Not Available Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Anorexigenic Agents

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point134.5 °CNot Available Boiling PointNot AvailableNot Available Water Solubility2.43e+00 g/LNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility2.43 mg/mLALOGPS logP2.01ALOGPS logP2.17ChemAxon logS-1.9ALOGPS pKa (Strongest Basic)7.28ChemAxon Physiological Charge1ChemAxon Hydrogen Acceptor Count2ChemAxon Hydrogen Donor Count0ChemAxon Polar Surface Area12.47 Å2ChemAxon Rotatable Bond Count1ChemAxon Refractivity57.76 m3·mol-1ChemAxon Polarizability21.99 Å3ChemAxon Number of Rings2ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01579

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01579

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01579 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    11950 KEGG Compound ID

    C07904 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Phendimetrazine NuGOwiki Link

    HMDB15519 Metagene Link

    HMDB15519 METLIN ID

    Not Available PubChem Compound

    12460 PDB ID

    Not Available ChEBI ID

    674499

    Product: Tetrabenazine

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not 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 ]

    PMID: 7539265

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