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Altropane
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

Altropane

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.


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