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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
  • 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
  • 156375
ChemSpider
  • 137706
UNII
  • LV23B78IJC
ChEMBL
  • ChEMBL1201308
CompTox Dashboard (EPA)
  • DTXSID50997294
Chemical and physical data
FormulaC12H18123IN
Molar mass299.278 g/mol
3D model (JSmol)
  • Interactive image
  • CC(C)NC(C)Cc1ccc(cc1)I
  • 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.[citation needed] However, based on structure-activity relationships, it may also be highly neurotoxic to serotonergic and dopaminergic neurons similarly to most other para-halogenated amphetamines.[citation needed]

See also edit

References edit

  1. ^ a b Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 562. ISBN 978-3-88763-075-1. Retrieved 25 April 2012.
  2. ^ a b 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.

iofetamine, 123i, iofetamine, iodine, 123i, brand, names, perfusamine, spectamine, isopropyl, 123i, iodoamphetamine, lipid, soluble, amine, radiopharmaceutical, drug, used, cerebral, blood, perfusion, imaging, with, single, photon, emission, computed, tomograp. 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 dataATC codeV09AB01 WHO Legal statusLegal statusIn general Prescription only Pharmacokinetic dataProtein binding lt 10 IdentifiersIUPAC name 1 4 123I iodophenyl N isopropyl 2 propanamineCAS Number75917 92 9 85068 76 4 non labeled 95896 48 3 123I labeled HCl PubChem CID156375ChemSpider137706UNIILV23B78IJCChEMBLChEMBL1201308CompTox Dashboard EPA DTXSID50997294Chemical and physical dataFormulaC12H18123INMolar mass299 278 g mol3D model JSmol Interactive imageSMILES CC C NC C Cc1ccc cc1 IInChI 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 4Key ISEHJSHTIVKELA DCWJVSPSSA NAn 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 citation needed However based on structure activity relationships it may also be highly neurotoxic to serotonergic and dopaminergic neurons similarly to most other para halogenated amphetamines citation needed See also editp Iodoamphetamine N IsopropylamphetamineReferences edit a b Index Nominum 2000 International Drug Directory Taylor amp Francis US 2000 p 562 ISBN 978 3 88763 075 1 Retrieved 25 April 2012 a b 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 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 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 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 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 Retrieved from https en wikipedia org w index php title Iofetamine 123I amp oldid 1156531553, wikipedia, wiki, book, books, library,

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