Altropane

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]

Altropane
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • Methyl (1R,2S,3S,5S)-3-(4-fluorophenyl)-8-[(E)-3-iodoprop-2-enyl]-8-azabicyclo[3.2.1]octane-2-carboxylate
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC18H21FINO2
Molar mass429.2694 g·mol−1
3D model (JSmol)
SMILES
  • COC(=O)[C@@H]1[C@H]2CC[C@H](N2C\C=C\I)C[C@@H]1C3=CC=C(C=C3)F
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 Y
  • Key:GTQLIPQFXVKRKJ-UNSMHXHVSA-N Y
  (verify)

References
  1. Elmaleh DR, Fischman AJ, Shoup TM, Byon C, Hanson RN, Liang AY, et al. (July 1996). "Preparation and biological evaluation of iodine-125-IACFT: a selective SPECT agent for imaging dopamine transporter sites". Journal of Nuclear Medicine. 37 (7): 1197–202. PMID 8965198.
  2. Fischman AJ, Bonab AA, Babich JW, Palmer EP, Alpert NM, Elmaleh DR, et al. (June 1998). "Rapid detection of Parkinson's disease by SPECT with altropane: a selective ligand for dopamine transporters". Synapse. 29 (2): 128–41. doi:10.1002/(SICI)1098-2396(199806)29:2<128::AID-SYN4>3.0.CO;2-9. PMID 9593103.
  3. Cattabeni F (November 2002). "Altropane (Boston Life Science)". Current Opinion in Investigational Drugs. 3 (11): 1647–51. PMID 12476968.
  4. Spencer TJ, Biederman J, Madras BK, Dougherty DD, Bonab AA, Livni E, et al. (November 2007). "Further evidence of dopamine transporter dysregulation in ADHD: a controlled PET imaging study using altropane". Biological Psychiatry. 62 (9): 1059–61. doi:10.1016/j.biopsych.2006.12.008. PMC 2715944. PMID 17511972.
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