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    N-Iodoallyl-2-Carbomethoxy-3-4-Fluorophenyl-Tropane

    ACTIVE PHARMA INGREDIENTS

    PharmaCompass
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    2D Structure
    Also known as: 180468-34-2, 1q4092099o, 8-azabicyclo(3.2.1)octane-2-carboxylic acid, 3-(4-fluorophenyl)-8-((2e)-3-iodo-2-propenyl)-, methyl ester, (1r,2s,3s,5s)-, Iacft, Methyl (1r,2s,3s,5s)-3-(4-fluorophenyl)-8-[(e)-3-iodoprop-2-enyl]-8-azabicyclo[3.2.1]octane-2-carboxylate, Unii-1q4092099o
    Molecular Formula
    C18H21FINO2
    Molecular Weight
    429.3  g/mol
    InChI Key
    GTQLIPQFXVKRKJ-UNSMHXHVSA-N
    FDA UNII
    1Q4092099O
    Boston Life Sciences (BLS) is developing Altropane as a potential radio-imaging agent to be used with single photon emission tomography (SPECT), for the early diagnosis of Parkinson's disease (PD) and attention deficit hyperactivity disorder (ADHD).
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    methyl (1R,2S,3S,5S)-3-(4-fluorophenyl)-8-[(E)-3-iodoprop-2-enyl]-8-azabicyclo[3.2.1]octane-2-carboxylate
    2.1.2 InChI
    InChI=1S/C18H21FINO2/c1-23-18(22)17-15(12-3-5-13(19)6-4-12)11-14-7-8-16(17)21(14)10-2-9-20/h2-6,9,14-17H,7-8,10-11H2,1H3/b9-2+/t14-,15+,16+,17-/m0/s1
    2.1.3 InChI Key
    GTQLIPQFXVKRKJ-UNSMHXHVSA-N
    2.1.4 Canonical SMILES
    COC(=O)C1C2CCC(N2CC=CI)CC1C3=CC=C(C=C3)F
    2.1.5 Isomeric SMILES
    COC(=O)[C@@H]1[C@H]2CC[C@H](N2C/C=C/I)C[C@@H]1C3=CC=C(C=C3)F
    2.2 Other Identifiers
    2.2.1 UNII
    1Q4092099O
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 2-carbomethoxy-3-(4-fluorophenyl)-n-(1-iodoprop-1-en-3-yl)nortropane

    2. Iacft

    3. N-iodoallyl-2-carbomethoxy-3-(4-fluorophenyl)tropane

    2.3.2 Depositor-Supplied Synonyms

    1. 180468-34-2

    2. 1q4092099o

    3. 8-azabicyclo(3.2.1)octane-2-carboxylic Acid, 3-(4-fluorophenyl)-8-((2e)-3-iodo-2-propenyl)-, Methyl Ester, (1r,2s,3s,5s)-

    4. Iacft

    5. Methyl (1r,2s,3s,5s)-3-(4-fluorophenyl)-8-[(e)-3-iodoprop-2-enyl]-8-azabicyclo[3.2.1]octane-2-carboxylate

    6. Unii-1q4092099o

    7. Iacft [mi]

    8. N-iodoallyl-2-carbomethoxy-3-(4-fluorophenyl)tropane

    9. Schembl1650069

    10. Chembl4301492

    11. Chebi:135696

    12. Dtxsid901027571

    13. 2beta-carbomethoxy-3beta-(4-fluorophenyl)-n-(3-iodo-e-allyl)nortropane

    14. Db04947

    15. Q4737006

    16. (1r,5s)-3beta-(4-fluorophenyl)-8-(3-iodoallyl)-8-demethyltropane-2beta-carboxylic Acid Methyl Ester

    17. (2r)-1-[(e)-3-iodoallyl]-2alpha,6alpha-ethano-3beta-(methoxycarbonyl)-4beta-(4-fluorophenyl)piperidine

    18. 8-azabicyclo(3.2.1)octane-2-carboxylic Acid, 3-(4-fluorophenyl)-8-((2e)-3-iodo-2-propen-1-yl)-, Methyl Ester, (1r,2s,3s,5s)-

    19. 8-azabicyclo(3.2.1)octane-2-carboxylic Acid, 3-(4-fluorophenyl)-8-(3-iodo-2-propenyl)-, Methyl Ester, (1r-(1.alpha.,2.alpha.,3.alpha.,5.alpha.,8(e)))-

    20. 8-azabicyclo(3.2.1)octane-2-carboxylic Acid, 3-(4-fluorophenyl)-8-(3-iodo-2-propenyl)-, Methyl Ester, (1r-(1alpha,2alpha,3alpha,5alpha,8(e)))-

    2.4 Create Date
    2006-04-28
    3 Chemical and Physical Properties
    Molecular Weight 429.3 g/mol
    Molecular Formula C18H21FINO2
    XLogP33.9
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count5
    Exact Mass429.06010 g/mol
    Monoisotopic Mass429.06010 g/mol
    Topological Polar Surface Area29.5 Ų
    Heavy Atom Count23
    Formal Charge0
    Complexity450
    Isotope Atom Count0
    Defined Atom Stereocenter Count4
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Investigated for use/treatment in attention deficit/hyperactivity disorder (ADHD), parkinson's disease, and pediatric indications.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Altropane is a molecular-imaging agent that specifically binds to the dopamine transporter (DAT) protein found on the surface of dopamine-producing neurons, making it visible during SPECT imaging. Since most forms of Parkinsonian Syndromes result in a decreased number of dopamine-producing cells, it would be expected that these patients also have fewer DATs than do patients without PS. Thus, it is believed that altropane used in conjunction with SPECT imaging could be a useful test to distinguish Parkinsonian Syndrome tremors from non-Parkinsonian tremor: non-Parkinsonian patients would have more altropane-binding visible in the SPECT image, while Parkinsonian patients would have less.

    5.2 Mechanism of Action

    Positron emission tomography (PET) cameras are expensive and scarce, and the tests are non-reimbursable. A less costly and more available test such as a single photon emission computed tomography (SPECT) may be helpful in the diagnosis of early or atypical Parkinson's disease (PD) if its sensitivity is comparable to a PET scan. Altropane is an iodinated form of the N-allyl analog of WIN 35,428 which acts as a dopamine transport inhibitor. When radiolabeled with the gamma emitting isotope [123I], altropane serves as a SPECT ligand with high affinity and selectivity for the dopamine transporter. It is a good marker for dopamine neurons and is useful in detecting PD.