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Benzphetamine

July 24, 2017
Common Name

Benzphetamine Description

Benzphetamine is only found in individuals that have used or taken this drug. It is a sympathomimetic agent with properties similar to dextroamphetamine. It is used in the treatment of obesity. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1222)Although the mechanism of action of the sympathomimetic appetite suppressants in the treatment of obesity is not flily known, these medications have pharmacological effects similar to those of amphetamines. Amphetamine and related sympathomimetic medications (such as benzphetamine) are thought to stimliate the release of norepinephrine and/or dopamine from storage sites in nerve terminals in the lateral hypothalamic feeding center, thereby producing a decrease in appetite. This release is mediated by the binding of benzphetamine to centrally located adrenergic receptors. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source (+)-BenzphetamineChEBI (+)-N,alpha-Dimethyl-N-(phenylmethyl)-benzeneethanamineChEBI (+)-N-Benzyl-N,alpha-dimethylphenethylamineChEBI (AlphaS)-N,alpha-dimethylphenethylamineChEBI (S)-(+)-BenzphetamineChEBI (S)-(+)-N-Benzyl-N,alpha-dimethylphenethylamineChEBI (S)-BenzphetamineChEBI BenzaphetamineChEBI BenzfetaminaChEBI BenzfetamineChEBI BenzfetaminumChEBI BenzylamphetamineChEBI D-N-Methyl-N-benzyl-beta-phenylisopropylamineChEBI N-Methyl-1-phenyl-N-(phenylmethyl)propan-2-amineChEBI (+)-N,a-Dimethyl-N-(phenylmethyl)-benzeneethanamineGenerator (+)-N,α-dimethyl-N-(phenylmethyl)-benzeneethanamineGenerator (+)-N-Benzyl-N,a-dimethylphenethylamineGenerator (+)-N-Benzyl-N,α-dimethylphenethylamineGenerator (AlphaS)-N,a-dimethylphenethylamineGenerator (AlphaS)-N,α-dimethylphenethylamineGenerator (S)-(+)-N-Benzyl-N,a-dimethylphenethylamineGenerator (S)-(+)-N-Benzyl-N,α-dimethylphenethylamineGenerator D-N-Methyl-N-benzyl-b-phenylisopropylamineGenerator D-N-Methyl-N-benzyl-β-phenylisopropylamineGenerator Pfizer brand OF benzfetamine hydrochlorideMeSH DidrexMeSH

Chemical Formlia

C17H21N Average Molecliar Weight

239.3553 Monoisotopic Molecliar Weight

239.167399677 IUPAC Name

benzyl(methyl)[(2S)-1-phenylpropan-2-yl]amine Traditional Name

benzphetamine CAS Registry Number

156-08-1 SMILES

C[C@@H](CC1=CC=CC=C1)N(C)CC1=CC=CC=C1

InChI Identifier

InChI=1S/C17H21N/c1-15(13-16-9-5-3-6-10-16)18(2)14-17-11-7-4-8-12-17/h3-12,15H,13-14H2,1-2H3/t15-/m0/s1

InChI Key

YXKTVDFXDRQTKV-HNNXBMFYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine. Kingdom

Chemical entities Super Class

Organic compounds Class

Benzenoids Sub Class

Benzene and substituted derivatives Direct Parent

Amphetamines and derivatives Alternative Parents

  • Phenylpropanes
  • Phenylmethylamines
  • Benzylamines
  • Aralkylamines
  • Trialkylamines
  • Organopnictogen compounds
  • Hydrocarbon derivatives

    • Substituents

  • Amphetamine or derivatives
  • Phenylpropane
  • Phenylmethylamine
  • Benzylamine
  • Aralkylamine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound

    • Molecliar Framework

    Aromatic homomonocyclic compounds External Descriptors

  • tertiary amine (CHEBI:3044 )
  • amphetamines (CHEBI:3044 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Adrenergic Agents
  • Adrenergic Uptake Inhibitors
  • Central Nervous System Agents
  • Central Nervous System Stimliants
  • Dopamine Agents
  • Dopamine Uptake Inhibitors
  • Sympathomimetics

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point152 – 153 °CNot Available Boiling PointNot AvailableNot Available Water Solubility2.33e-02 g/LNot Available LogP4.1Not Available

    Predicted Properties

    Property Value Source Water Solubility0.023 mg/mLALOGPS logP3.72ALOGPS logP4.34ChemAxon logS-4ALOGPS pKa (Strongest Basic)9.8ChemAxon Physiological Charge1ChemAxon Hydrogen Acceptor Count1ChemAxon Hydrogen Donor Count0ChemAxon Polar Surface Area3.24 Å2ChemAxon Rotatable Bond Count5ChemAxon Refractivity78.39 m3·mol-1ChemAxon Polarizability29.03 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

  • Cytoplasm
  • 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 DB00865

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00865

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Predicted Concentrations

    Biofluid Value Original age Original sex Original condition Comments Blood0-4 uMAdlit (>18 years old)BothNormalPredicted based on drug qualities Blood0-2 umol/mmol creatinineAdlit (>18 years old)BothNormalPredicted based on drug qualities

    Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB00865 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

    4470556 KEGG Compound ID

    C07538 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Benzphetamine NuGOwiki Link

    HMDB15003 Metagene Link

    HMDB15003 METLIN ID

    Not Available PubChem Compound

    5311017 PDB ID

    Not Available ChEBI ID

    3044

    Product: Novaluron

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

    Enzymes

    General function:
    Involved in oxidoreductase activity
    Specific function:
    This enzyme is required for electron transfer from NADP to cytochrome P450 in microsomes. It can also provide electron transfer to heme oxygenase and cytochrome B5.
    Gene Name:
    POR
    Uniprot ID:
    P16435
    Molecular weight:
    77047.575
    References
    1. Kanaeva IP, Nikityuk OV, Davydov DR, Dedinskii IR, Koen YM, Kuznetsova GP, Skotselyas ED, Bachmanova GI, Archakov AI: Comparative study of monomeric reconstituted and membrane microsomal monooxygenase systems of the rabbit liver. II. Kinetic parameters of reductase and monooxygenase reactions. Arch Biochem Biophys. 1992 Nov 1;298(2):403-12. [PubMed:1416971 ]
    2. Matsumoto T, Emi Y, Kawabata S, Omura T: Purification and characterization of three male-specific and one female-specific forms of cytochrome P-450 from rat liver microsomes. J Biochem. 1986 Nov;100(5):1359-71. [PubMed:2434473 ]
    3. Kojima H, Takahashi K, Sakane F, Koyama J: Purification and characterization of NADPH-cytochrome c reductase from porcine polymorphonuclear leukocytes. J Biochem. 1987 Nov;102(5):1083-8. [PubMed:3125159 ]
    4. Dutton DR, McMillen SK, Parkinson A: Purification of rat liver microsomal cytochrome P-450b without the use of nonionic detergent. J Biochem Toxicol. 1988 Summer;3:131-45. [PubMed:3148724 ]
    5. Halpert JR, Miller NE, Gorsky LD: On the mechanism of the inactivation of the major phenobarbital-inducible isozyme of rat liver cytochrome P-450 by chloramphenicol. J Biol Chem. 1985 Jul 15;260(14):8397-403. [PubMed:3924914 ]
    General function:
    Involved in monooxygenase activity
    Specific function:
    Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
    Gene Name:
    CYP3A4
    Uniprot ID:
    P08684
    Molecular weight:
    57255.585
    References
    1. Seree EJ, Pisano PJ, Placidi M, Rahmani R, Barra YA: Identification of the human and animal hepatic cytochromes P450 involved in clonazepam metabolism. Fundam Clin Pharmacol. 1993;7(2):69-75. [PubMed:8486332 ]
    General function:
    Involved in monooxygenase activity
    Specific function:
    Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
    Gene Name:
    CYP2B6
    Uniprot ID:
    P20813
    Molecular weight:
    56277.81
    References
    1. Bumpus NN, Sridar C, Kent UM, Hollenberg PF: The naturally occurring cytochrome P450 (P450) 2B6 K262R mutant of P450 2B6 exhibits alterations in substrate metabolism and inactivation. Drug Metab Dispos. 2005 Jun;33(6):795-802. Epub 2005 Mar 15. [PubMed:15769884 ]
    2. Shebley M, Kent UM, Ballou DP, Hollenberg PF: Mechanistic analysis of the inactivation of cytochrome P450 2B6 by phencyclidine: effects on substrate binding, electron transfer, and uncoupling. Drug Metab Dispos. 2009 Apr;37(4):745-52. doi: 10.1124/dmd.108.024661. Epub 2009 Jan 14. [PubMed:19144770 ]
    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
    Gene Name:
    ADRA2A
    Uniprot ID:
    P08913
    Molecular weight:
    48956.3
    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 ]
    General function:
    Involved in transmembrane transport
    Specific function:
    Involved in the ATP-dependent vesicular transport of biogenic amine neurotransmitters. Pumps cytosolic monoamines including dopamine, norepinephrine, serotonin, and histamine into synaptic vesicles. Requisite for vesicular amine storage prior to secretion via exocytosis
    Gene Name:
    SLC18A2
    Uniprot ID:
    Q05940
    Molecular weight:
    55712.1
    References
    1. Sulzer D, Chen TK, Lau YY, Kristensen H, Rayport S, Ewing A: Amphetamine redistributes dopamine from synaptic vesicles to the cytosol and promotes reverse transport. J Neurosci. 1995 May;15(5 Pt 2):4102-8. [PubMed:7751968 ]
    General function:
    Involved in neurotransmitter:sodium symporter activity
    Specific function:
    Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
    Gene Name:
    SLC6A3
    Uniprot ID:
    Q01959
    Molecular weight:
    68494.255
    References
    1. Sulzer D, Sonders MS, Poulsen NW, Galli A: Mechanisms of neurotransmitter release by amphetamines: a review. Prog Neurobiol. 2005 Apr;75(6):406-33. [PubMed:15955613 ]
    2. Kahlig KM, Binda F, Khoshbouei H, Blakely RD, McMahon DG, Javitch JA, Galli A: Amphetamine induces dopamine efflux through a dopamine transporter channel. Proc Natl Acad Sci U S A. 2005 Mar 1;102(9):3495-500. Epub 2005 Feb 22. [PubMed:15728379 ]
    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 ]

    PMID: 15690449

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