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Isometheptene

July 24, 2017
Common Name

Isometheptene Description

Isometheptene is only found in individuals that have used or taken this drug. It is a sympathomimetic drug which causes vasoconstriction. It is used for treating migraines and tension headaches.Isometheptenes vasoconstricting properties arise through activation of the sympathetic nervous system via epinephrine and norepinephrine (or their molecliar analogues as is the case with this drug). These compounds elicites smooth muscle activation leading to vasoconstriction. These compounds interact with cell surface adrenergic receptors. Such stimlii reslit in a signal transduction cascade that leads to increased intracellliar calcium from the sarcoplasmic reticlium through IP3 mediated calcium release, as well as enhanced calcium entry across the sarcolemma through calcium channels. The rise in intracellliar calcium complexes with calmodliin, which in turn activates myosin light chain kinase. This enzyme is responsible for phosphorylating the light chain of myosin to stimliate cross bridge cycling.Once elevated, the intracellliar calcium concentration is returned to its basal level through a variety of protein pumps and calcium exchangers located on the plasma membrane and sarcoplasmic reticlium. This reduction in calcium removes the stimlius necessary for contraction allowing for a return to baseline. The drug can also cause vesicliar displacement of noradrenaline from the neuron into the synapse with a similar effect as tyramine. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source MidridMeSH Isometheptene, monomaleateMeSH N,1,5-Trimethyl-4-hexenylamineMeSH Isometheptene monohydrochorideMeSH Isometheptene, maleateMeSH Isometheptene, maleate(+-)-isomerMeSH Isometheptene, monotartrateMeSH Isometheptene, mucate (2:1)MeSH Isometheptene, (+-)-isomerMeSH Isometheptene, monomaleate(+-)-isomerMeSH

Chemical Formlia

C9H19N Average Molecliar Weight

141.2539 Monoisotopic Molecliar Weight

141.151749613 IUPAC Name

methyl(6-methylhept-5-en-2-yl)amine Traditional Name

isometheptene CAS Registry Number

503-01-5 SMILES

CNC(C)CCC=C(C)C

InChI Identifier

InChI=1S/C9H19N/c1-8(2)6-5-7-9(3)10-4/h6,9-10H,5,7H2,1-4H3

InChI Key

XVQUOJBERHHONY-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic nitrogen compounds Sub Class

Organonitrogen compounds Direct Parent

Dialkylamines Alternative Parents

  • Organopnictogen compounds
  • Hydrocarbon derivatives

    • Substituents

  • Secondary aliphatic amine
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound

    • Molecliar Framework

    Aliphatic acyclic compounds External Descriptors

    Not Available Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Sympathomimetics

    • Application

  • Nutrients
  • Pharmaceutical
  • Stabilizers
  • Surfactants and Emlisifiers

    • Cellliar locations

  • Cytoplasm
  • Extracellliar
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility3.06 mg/mLALOGPS logP2.07ALOGPS logP2.32ChemAxon logS-1.7ALOGPS pKa (Strongest Basic)10.67ChemAxon Physiological Charge1ChemAxon Hydrogen Acceptor Count1ChemAxon Hydrogen Donor Count1ChemAxon Polar Surface Area12.03 Å2ChemAxon Rotatable Bond Count4ChemAxon Refractivity47.59 m3·mol-1ChemAxon Polarizability18.81 Å3ChemAxon Number of Rings0ChemAxon 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
  • Extracellliar
  • 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 DB06706

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06706

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB06706 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

    21106328 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Isometheptene NuGOwiki Link

    HMDB15651 Metagene Link

    HMDB15651 METLIN ID

    Not Available PubChem Compound

    22297 PDB ID

    Not Available ChEBI ID

    1178590

    Product: Lamotrigine

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

    Enzymes

    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. Valdivia LF, Centurion D, Perusquia M, Arulmani U, Saxena PR, Villalon CM: Pharmacological analysis of the mechanisms involved in the tachycardic and vasopressor responses to the antimigraine agent, isometheptene, in pithed rats. Life Sci. 2004 May 14;74(26):3223-34. [PubMed:15094323 ]
    2. 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 ]
    3. 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 ]
    4. Parker EM, Cubeddu LX: Comparative effects of amphetamine, phenylethylamine and related drugs on dopamine efflux, dopamine uptake and mazindol binding. J Pharmacol Exp Ther. 1988 Apr;245(1):199-210. [PubMed:3129549 ]
    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. Valdivia LF, Centurion D, Perusquia M, Arulmani U, Saxena PR, Villalon CM: Pharmacological analysis of the mechanisms involved in the tachycardic and vasopressor responses to the antimigraine agent, isometheptene, in pithed rats. Life Sci. 2004 May 14;74(26):3223-34. [PubMed:15094323 ]
    2. Parker EM, Cubeddu LX: Comparative effects of amphetamine, phenylethylamine and related drugs on dopamine efflux, dopamine uptake and mazindol binding. J Pharmacol Exp Ther. 1988 Apr;245(1):199-210. [PubMed:3129549 ]

    PMID: 14654105

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