Altropane

Stimulant drug
  • none
Identifiers
  • Methyl (1R,2S,3S,5S)-3-(4-fluorophenyl)-8-[(E)-3-iodoprop-2-enyl]-8-azabicyclo[3.2.1]octane-2-carboxylate
CAS Number
  • 180468-34-2 checkY
PubChem CID
  • 6440180
ChemSpider
  • 4944487 checkY
UNII
  • 1Q4092099O
Chemical and physical dataFormulaC18H21FINO2Molar mass429.274 g·mol−13D model (JSmol)
  • Interactive image
  • 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 checkY
  • Key:GTQLIPQFXVKRKJ-UNSMHXHVSA-N checkY
  (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, 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. S2CID 30543189.
  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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Stimulants
AdamantanesAdenosine antagonistsAlkylaminesAmpakinesArylcyclohexylaminesBenzazepinesCathinonesCholinergicsConvulsantsEugeroicsOxazolinesPhenethylamines
PhenylmorpholinesPiperazinesPiperidinesPyrrolidinesRacetamsTropanesTryptaminesOthers
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DATTooltip Dopamine transporter
(DRIsTooltip Dopamine reuptake inhibitors)
NETTooltip Norepinephrine transporter
(NRIsTooltip Norepinephrine reuptake inhibitors)
SERTTooltip Serotonin transporter
(SRIsTooltip Serotonin reuptake inhibitors)
VMATsTooltip Vesicular monoamine transporters
Others
See also: Receptor/signaling modulators • Monoamine releasing agents • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins
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2-Carboxymethyl Esters
(3,4-Disubstituted Phenyl)-tropanes
Arylcarboxy
Carboxyalkyl
Acyl
  • PTT/WF-11
  • WF-23
  • PIT/WF-21
  • WF-33
β,α Stereochemistry
α,β Stereochemistry
Heterocycles: 3-Substituted-isoxazol-5-yl
Heterocycles: 3-Substituted-1,2,4-oxadiazole
N-alkyl
  • FP-β-CPPIT
  • FE-β-CPPIT
  • Altropane
  • Ioflupane (123I)
N-replaced (S,O,C)
Irreversible
Nortropanes (N-demethylated)


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