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RTI-121

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
RTI-121
Legal status
Legal status
  • In general: unscheduled
Identifiers
  • Propan-2-yl (1R,2S,3S)-3-(4-iodophenyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
CAS Number
PubChemCID
ChemSpider
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC18H24INO2
Molar mass413.299 g·mol−1
3D model (JSmol)
  • CN3[C@@H]1CCC3C[C@@H]([C@@H]1C(=O)OC(C)C)c2ccc(I)cc2
  • InChI=1S/C18H24INO2/c1-11(2)22-18(21)17-15(12-4-6-13(19)7-5-12)10-14-8-9-16(17)20(14)3/h4-7,11,14-17H,8-10H2,1-3H3/t14?,15-,16-,17+/m1/s1 checkY
  • Key:ZAQLTGAFVMGUMB-IFFAKLHKSA-N checkY
  (verify)

(–)-2β-Carboisopropoxy-3β-(4-iodophenyl)tropane (RTI-4229-121,IPCIT) is astimulant drug used in scientific research, which was developed in the early 1990s.[1] RTI-121 is aphenyltropane based, highly selectivedopamine reuptake inhibitor[2] and is derived frommethylecgonidine. RTI-121 is a potent and long-lasting stimulant, producing stimulant effects for more than 10 hours after a single dose in mice[3] which would limit its potential uses in humans, as it might have significantabuse potential if used outside a medical setting. However RTI-121 occupies the dopamine transporter more slowly thancocaine, and so might have lower abuse potential than cocaine itself.[4]

Uses

[edit]

RTI-121 is mainly used in scientific research into thedopamine reuptake transporter. It is more selective for the dopamine transporter than other DAT radioligands such asβ-CIT, and so has less nonspecific binding and produces "cleaner" images.[5][6] Variousradiolabelled forms of RTI-121 (with different radioactiveisotopes ofiodine used depending on the application) are used in both humans and animals to map the distribution ofdopamine transporters in thebrain.[7][8]

Legal status

[edit]

RTI-121 not specified as controlled substance in any country as of 2007. Some jurisdictions such as the United States, Australia, and New Zealand, however, might however consider RTI-121 to be acontrolled substance analogue of cocaine on the grounds of its related chemical structure.

See also

[edit]

References

[edit]
  1. ^Scheffel U, Dannals RF, Wong DF, Yokoi F, Carroll FI, Kuhar MJ (November 1992). "Dopamine transporter imaging with novel, selective cocaine analogs".NeuroReport.3 (11):969–72.doi:10.1097/00001756-199211000-00005.PMID 1482766.
  2. ^Boja JW, Cadet JL, Kopajtic TA, Lever J, Seltzman HH, Wyrick CD, et al. (April 1995). "Selective labeling of the dopamine transporter by the high affinity ligand 3 beta-(4-[125I]iodophenyl)tropane-2 beta-carboxylic acid isopropyl ester".Molecular Pharmacology.47 (4):779–86.PMID 7723739.
  3. ^Fleckenstein AE, Kopajtic TA, Boja JW, Carroll FI, Kuhar MJ (September 1996). "Highly potent cocaine analogs cause long-lasting increases in locomotor activity".European Journal of Pharmacology.311 (2–3):109–14.doi:10.1016/0014-2999(96)00423-2.PMID 8891589.
  4. ^Stathis M, Scheffel U, Lever SZ, Boja JW, Carroll FI, Kuhar MJ (June 1995)."Rate of binding of various inhibitors at the dopamine transporter in vivo".Psychopharmacology.119 (4):376–84.doi:10.1007/BF02245852.PMID 7480516.S2CID 20022021.
  5. ^Scanley BE, al-Tikriti MS, Gandelman MS, Laruelle M, Zea-Ponce Y, Baldwin RM, et al. (January 1995). "Comparison of [123I]beta-CIT and [123I]IPCIT as single-photon emission tomography radiotracers for the dopamine transporter in nonhuman primates".European Journal of Nuclear Medicine.22 (1):4–11.doi:10.1007/BF00997241.PMID 7698153.S2CID 20406294.
  6. ^Scanley BE, Gandelman MS, Laruelle M, Al-Tikriti MS, Baldwin RM, Zoghbi SS, et al. (January 2000)."[123I]IPCIT and [123I]beta-CIT as SPECT tracers for the dopamine transporter: a comparative analysis in nonhuman primates".Nuclear Medicine and Biology.27 (1):13–21.doi:10.1016/s0969-8051(99)00083-9.PMID 10755641.
  7. ^Chen NH, Ding JH, Wang YL (March 1997). "Characterization of [125I]RTI-121 binding to dopamine transporter in vitro".Zhongguo Yao Li Xue Bao = Acta Pharmacologica Sinica.18 (2):115–20.PMID 10072960.
  8. ^Lever JR, Scheffel U, Stathis M, Seltzman HH, Wyrick CD, Abraham P, et al. (April 1996)."Synthesis and in vivo studies of a selective ligand for the dopamine transporter: 3 beta-(4-[125I]iodophenyl) tropan-2 beta-carboxylic acid isopropyl ester ([125I]RTI-121)".Nuclear Medicine and Biology.23 (3):277–84.doi:10.1016/0969-8051(95)02074-8.PMID 8782237.
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