Altropane

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Altropane
Altropane.svg
Systematic (IUPAC) name
Methyl (1R,2S,3S,5S)-3-(4-fluorophenyl)-8-[(E)-3-iodoprop-2-enyl]-8-azabicyclo[3.2.1]octane-2-carboxylate
Identifiers
CAS Number 180468-34-2 YesY
ATC code none
PubChem CID: 6440180
ChemSpider 4944487 YesY
Chemical data
Formula C18H21FINO2
Molecular mass 429.2694
  • COC(=O)[C@@H]1[C@H]2CC[C@H](N2C\C=C\I)C[C@@H]1C3=CC=C(C=C3)F
  • 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 YesY
  • Key:GTQLIPQFXVKRKJ-UNSMHXHVSA-N YesY
  (verify)

Altropane, (O-587, IACFT, 2β-carbomethoxy-3β-(4-fluorophenyl)-N-((E)-3-iodo-prop-2-enyl)tropane) is a phenyltropane derivative which acts as a potent dopamine reuptake inhibitor and long-acting stimulant drug. It has mainly been used as the 125I radiolabelled form for mapping the distribution of dopamine transporters in the brain,[1] and consequently this has led to its development as a potential diagnostic tool for early detection of Parkinson's disease.[2] It is also being investigated for potential use in the diagnosis and treatment of attention deficit hyperactivity disorder (ADHD).[3][4]

References

  1. ↑ Elmaleh DR, Fischman AJ, Shoup TM, Byon C, Hanson RN, Liang AY, Meltzer PC, Madras BK. Preparation and biological evaluation of iodine-125-IACFT: a selective SPECT agent for imaging dopamine transporter sites. Journal of Nuclear Medicine. 1996 Jul;37(7):1197-202. PMID 8965198
  2. ↑ Fischman AJ, Bonab AA, Babich JW, Palmer EP, Alpert NM, Elmaleh DR, Callahan RJ, Barrow SA, Graham W, Meltzer PC, Hanson RN, Madras BK. Rapid detection of Parkinson's disease by SPECT with altropane: a selective ligand for dopamine transporters. Synapse. 1998 Jun;29(2):128-41. PMID 9593103
  3. ↑ Cattabeni F. Altropane (Boston Life Science). Current Opinion in Investigational Drugs. 2002 Nov;3(11):1647-51. PMID 12476968
  4. ↑ Spencer TJ, Biederman J, Madras BK, Dougherty DD, Bonab AA, Livni E, Meltzer PC, Martin J, Rauch S, Fischman AJ. Further evidence of dopamine transporter dysregulation in ADHD: a controlled PET imaging study using altropane. Biological Psychiatry. 2007 Nov 1;62(9):1059-61. PMID 17511972


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