RTI-121

(–)-2β-Carboisopropoxy-3β-(4-iodophenyl)tropane (RTI-4229-121, IPCIT) is a stimulant drug used in scientific research, which was developed in the early 1990s.[1] RTI-121 is a phenyltropane based, highly selective dopamine reuptake inhibitor[2] and is derived from methylecgonidine. 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 significant abuse potential if used outside a medical setting. However RTI-121 occupies the dopamine transporter more slowly than cocaine, and so might have lower abuse potential than cocaine itself.[4]

RTI-121
Legal status
Legal status
  • In general: unscheduled
Identifiers
IUPAC name
  • Propan-2-yl (1R,2S,3S)-3-(4-iodophenyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H24INO2
Molar mass413.299 g·mol−1
3D model (JSmol)
SMILES
  • CN3[C@@H]1CCC3C[C@@H]([C@@H]1C(=O)OC(C)C)c2ccc(I)cc2
InChI
  • 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 Y
  • Key:ZAQLTGAFVMGUMB-IFFAKLHKSA-N Y
  (verify)

Uses

RTI-121 is mainly used in scientific research into the dopamine reuptake transporter. It is more selective for the dopamine transporter than other DAT radioligands such as β-CIT, and so has less nonspecific binding and produces "cleaner" images.[5][6] Various radiolabelled forms of RTI-121 (with different radioactive isotopes of iodine used depending on the application) are used in both humans and animals to map the distribution of dopamine transporters in the brain.[7][8]

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 a controlled substance analogue of cocaine on the grounds of its related chemical structure.

See also

References
  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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