Iofetamine (123I)

Iofetamine (iodine-123, 123I), brand names Perfusamine, SPECTamine), or N-isopropyl-(123I)-p-iodoamphetamine (IMP), is a lipid-soluble amine and radiopharmaceutical drug used in cerebral blood perfusion imaging with single-photon emission computed tomography (SPECT).[1][2][3] Labeled with the radioactive isotope iodine-123, it is approved for use in the United States as a diagnostic aid in determining the localization of and in the evaluation of non-lacunar stroke and complex partial seizures, as well as in the early diagnosis of Alzheimer's disease.[1][2]

Iofetamine (123I)
Clinical data
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding<10%
Identifiers
IUPAC name
  • 1-[4-(123I)iodophenyl]-N-isopropyl-2-propanamine
CAS Number
  • 75917-92-9
    85068-76-4 (non-labeled)
    95896-48-3 (123I-labeled HCl)
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H18123IN
Molar mass299.278 g/mol
3D model (JSmol)
SMILES
  • CC(C)NC(C)Cc1ccc(cc1)I
InChI
  • InChI=1S/C12H18IN/c1-9(2)14-10(3)8-11-4-6-12(13)7-5-11/h4-7,9-10,14H,8H2,1-3H3/i13-4
  • Key:ISEHJSHTIVKELA-DCWJVSPSSA-N

An analogue of amphetamine, iofetamine has shown to inhibit the reuptake of serotonin and norepinephrine as well as induce the release of these neurotransmitters and of dopamine with similar potencies to other amphetamines like d-amphetamine and p-chloroamphetamine.[4][5] In addition, on account of its high lipophilicity, iofetamine rapidly penetrates the blood-brain-barrier.[6] Accordingly, though not known to have been reported in the medical literature, iofetamine likely possesses psychostimulant and possibly entactogenic effects. However, based on structure-activity relationships, it may also be highly neurotoxic to serotonergic and dopaminergic neurons similarly to most other para-halogenated amphetamines.

See also

References
  1. Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 562. ISBN 978-3-88763-075-1. Retrieved 25 April 2012.
  2. Druckenbrod RW, Williams CC, Gelfand MJ (January 1989). "Iofetamine hydrochloride I 123: a new radiopharmaceutical for cerebral perfusion imaging". DICP: The Annals of Pharmacotherapy. 23 (1): 19–24. doi:10.1177/106002808902300103. PMID 2655294. S2CID 1649855.
  3. Holman BL, Hill TC, Magistretti PL (1982). "Brain imaging with emission computed tomography and radiolabeled amines". Investigative Radiology. 17 (3): 206–15. doi:10.1097/00004424-198201730-00002. PMID 6811496.
  4. Winchell HS, Horst WD, Braun L, Oldendorf WH, Hattner R, Parker H (October 1980). "N-isopropyl-[123I] p-iodoamphetamine: single-pass brain uptake and washout; binding to brain synaptosomes; and localization in dog and monkey brain". Journal of Nuclear Medicine. 21 (10): 947–52. PMID 6775056.
  5. de Jong BM, Feenstra MG, Ruijter JM, van Royen EA (March 1989). "Serotonin uptake in cerebral cortex cultures: imipramine-like inhibition by N-isopropyl-p-iodoamphetamine". Experimental Neurology. 103 (3): 297–9. doi:10.1016/0014-4886(89)90055-1. PMID 2920796. S2CID 23266659.
  6. Winchell HS, Baldwin RM, Lin TH (October 1980). "Development of I-123-labeled amines for brain studies: localization of I-123 iodophenylalkyl amines in rat brain". Journal of Nuclear Medicine. 21 (10): 940–6. PMID 7420195.
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