RTI-121
{{Short description|Chemical compound}}
{{Drugbox
| verifiedrevid = 401038485
| IUPAC_name = Propan-2-yl (1R,2S,3S)-3-(4-iodophenyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
| image = Phenyltropane 25a.svg
| width = 160
| tradename =
| pregnancy_AU =
| pregnancy_US =
| pregnancy_category =
| legal_AU =
| legal_CA =
| legal_UK =
| legal_US =
| legal_status = Unscheduled
| routes_of_administration =
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
| CAS_number = 146145-21-3
| ATC_prefix =
| ATC_suffix =
| PubChem = 122190
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 21106374
| C=18 | H=24 | I=1 | N=1 | O=2
| smiles = CN3[C@@H]1CCC3C[C@@H]([C@@H]1C(=O)OC(C)C)c2ccc(I)cc2
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ZAQLTGAFVMGUMB-IFFAKLHKSA-N
| melting_point =
| melting_high =
}}
(–)-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.{{cite journal | vauthors = Scheffel U, Dannals RF, Wong DF, Yokoi F, Carroll FI, Kuhar MJ | title = Dopamine transporter imaging with novel, selective cocaine analogs | journal = NeuroReport | volume = 3 | issue = 11 | pages = 969–72 | date = November 1992 | pmid = 1482766 | doi = 10.1097/00001756-199211000-00005 }} RTI-121 is a phenyltropane based, highly selective dopamine reuptake inhibitor{{cite journal | vauthors = Boja JW, Cadet JL, Kopajtic TA, Lever J, Seltzman HH, Wyrick CD, Lewin AH, Abraham P, Carroll FI | display-authors = 6 | title = Selective labeling of the dopamine transporter by the high affinity ligand 3 beta-(4-[125I]iodophenyl)tropane-2 beta-carboxylic acid isopropyl ester | journal = Molecular Pharmacology | volume = 47 | issue = 4 | pages = 779–86 | date = April 1995 | pmid = 7723739 }} 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{{cite journal | vauthors = Fleckenstein AE, Kopajtic TA, Boja JW, Carroll FI, Kuhar MJ | title = Highly potent cocaine analogs cause long-lasting increases in locomotor activity | journal = European Journal of Pharmacology | volume = 311 | issue = 2–3 | pages = 109–14 | date = September 1996 | pmid = 8891589 | doi = 10.1016/0014-2999(96)00423-2 }} 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.{{cite journal | vauthors = Stathis M, Scheffel U, Lever SZ, Boja JW, Carroll FI, Kuhar MJ | title = Rate of binding of various inhibitors at the dopamine transporter in vivo | journal = Psychopharmacology | volume = 119 | issue = 4 | pages = 376–84 | date = June 1995 | pmid = 7480516 | doi = 10.1007/BF02245852 | s2cid = 20022021 | url = https://zenodo.org/record/1232524 }}
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.{{cite journal | vauthors = Scanley BE, al-Tikriti MS, Gandelman MS, Laruelle M, Zea-Ponce Y, Baldwin RM, Zoghbi SS, Hoffer PB, Charney DS, Wang S | display-authors = 6 | title = Comparison of [123I]beta-CIT and [123I]IPCIT as single-photon emission tomography radiotracers for the dopamine transporter in nonhuman primates | journal = European Journal of Nuclear Medicine | volume = 22 | issue = 1 | pages = 4–11 | date = January 1995 | pmid = 7698153 | doi = 10.1007/BF00997241 | s2cid = 20406294 }}{{cite journal | vauthors = Scanley BE, Gandelman MS, Laruelle M, Al-Tikriti MS, Baldwin RM, Zoghbi SS, Hoffer PB, Wang S, Neumeyer JL, Innis RB | display-authors = 6 | title = [123I]IPCIT and [123I]beta-CIT as SPECT tracers for the dopamine transporter: a comparative analysis in nonhuman primates | journal = Nuclear Medicine and Biology | volume = 27 | issue = 1 | pages = 13–21 | date = January 2000 | pmid = 10755641 | doi = 10.1016/s0969-8051(99)00083-9 | doi-access = free }} 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.{{cite journal | vauthors = Chen NH, Ding JH, Wang YL | title = Characterization of [125I]RTI-121 binding to dopamine transporter in vitro | journal = Zhongguo Yao Li Xue Bao = Acta Pharmacologica Sinica | volume = 18 | issue = 2 | pages = 115–20 | date = March 1997 | pmid = 10072960 }}{{cite journal | vauthors = Lever JR, Scheffel U, Stathis M, Seltzman HH, Wyrick CD, Abraham P, Parham K, Thomas BF, Boja JW, Kuhar MJ, Carroll FI | display-authors = 6 | title = 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) | journal = Nuclear Medicine and Biology | volume = 23 | issue = 3 | pages = 277–84 | date = April 1996 | pmid = 8782237 | doi = 10.1016/0969-8051(95)02074-8 | doi-access = free }}
Legal status
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
{{reflist}}
{{Stimulants}}
{{Monoamine reuptake inhibitors}}
{{Phenyltropanes}}
Category:4-Iodophenyl compounds
Category:Dopamine reuptake inhibitors