My watch list

RTI-121


RTI-121
Systematic (IUPAC) name
propan-2-yl (1R,2S,3S)-3-(4-iodophenyl) -8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
Identifiers
CAS number	146145-21-3
ATC code	?
PubChem	122190
Chemical data
Formula	C₁₈H₂₄I N O₂
Mol. mass	413.29 g/mol
SMILES	search in eMolecules, PubChem
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status	Legal
Routes	?

(-)-2β-Carboisopropoxy-3β-(4-iodophenyl)tropane (RTI-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 of a strictly controlled medical setting. However RTI-121 occupies the dopamine transporter more slowly than cocaine, and so might have lower abuse potential than cocaine itself.^[4]

Additional recommended knowledge

Essential Laboratory Skills Guide

Daily Sensitivity Test

How to ensure accurate weighing results every day?

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]

Legal Status

RTI-121 is legal in all countries throughout the world as of 2007. Some jurisdictions such as the USA, Canada, Australia and New Zealand might however consider RTI-121 to be a controlled substance analogue of cocaine on the grounds of its related chemical structure.

References

^ Scheffel U, Dannals RF, Wong DF, Yokoi F, Carroll FI, Kuhar MJ. Dopamine transporter imaging with novel, selective cocaine analogs. Neuroreport. 1992 Nov;3(11):969-72.
^ Boja JW, Cadet JL, Kopajtic TA, Lever J, Seltzman HH, Wyrick CD, Lewin AH, Abraham P, Carroll FI. 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. 1995 Apr;47(4):779-86.
^ Fleckenstein AE, Kopajtic TA, Boja JW, Carroll FI, Kuhar MJ. Highly potent cocaine analogs cause long-lasting increases in locomotor activity. European Journal of Pharmacology. 1996 Sep 12;311(2-3):109-14.
^ Stathis M, Scheffel U, Lever SZ, Boja JW, Carroll FI, Kuhar MJ. Rate of binding of various inhibitors at the dopamine transporter in vivo. Psychopharmacology (Berlin). 1995 Jun;119(4):376-84.
^ Scanley BE, al-Tikriti MS, Gandelman MS, Laruelle M, Zea-Ponce Y, Baldwin RM, Zoghbi SS, Hoffer PB, Charney DS, Wang S, et al. 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. 1995 Jan;22(1):4-11.
^ Scanley BE, Gandelman MS, Laruelle M, Al-Tikriti MS, Baldwin RM, Zoghbi SS, Hoffer PB, Wang S, Neumeyer JL, Innis RB. [123I]IPCIT and [123I]beta-CIT as SPECT tracers for the dopamine transporter: a comparative analysis in nonhuman primates. Nuclear Medicine and Biology. 2000 Jan;27(1):13-21.
^ Chen NH, Ding JH, Wang YL. Characterization of [125I]RTI-121 binding to dopamine transporter in vitro. Zhongguo Yao Li Xue Bao. 1997 Mar;18(2):115-20.
^ Lever JR, Scheffel U, Stathis M, Seltzman HH, Wyrick CD, Abraham P, Parham K, Thomas BF, Boja JW, Kuhar MJ, Carroll FI. 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. 1996 Apr;23(3):277-84.

v • d • e Stimulants
Eugeroics	Adrafinil • Armodafinil • Carphedon • Modafinil
Phenethylamines	4-Fluoroamphetamine • 4-Fluoromethamphetamine • 4-Methylmethcathinone • 4-MTA • α-PPP • Amphechloral • Amphetamine (Dexamphetamine, Adderall) • Amphetaminil • Benzphetamine • Bupropion • Cathinone • Chlorphentermine • Clobenzorex • Clortermine • Cypenamine • Diethylpropion • Dimethoxyamphetamine • Dimethylamphetamine • Dimethylcathinone • Diphenyl prolinol • Ephedrine • Epinephrine • Ethcathinone • Ethylamphetamine • Fencamfamine • Fenethylline • Fenfluramine • Fenproporex • Feprosidnine • Furfenorex • Levomethamphetamine • Lisdexamfetamine • MDMA • Mefenorex • Methamphetamine • Methcathinone • Methoxyphedrine • Methylone • Octopamine • Parahydroxyamphetamine • PMA • PMEA • PMMA • PPAP • Phendimetrazine • Phenmetrazine • Phentermine • Phenylephrine • Phenylpropanolamine • Prolintane Propylamphetamine • Pseudoephedrine • Selegiline • Synephrine • Xylopropamine
Piperazines	BZP • MeOPP • MBZP • mCPP • 2C-B-BZP
Xanthines	Caffeine • Aminophylline • Paraxanthine • Theobromine • Theophylline
Tropanes	Brasofensine • CFT • Cocaethylene • Cocaine • Lometopane • RTI-121 • Tesofensine • Troparil
Cholinergics	Arecoline • Cotinine • Nicotine
Convulsants	Bicuculline • Gabazine • Pentetrazol • Picrotoxin • Strychnine • Thujone
Phenylaminooxazoles	4-Methyl-aminorex • Aminorex • Clominorex • Fenozolone • Fluminorex • Pemoline • Thozalinone
Others	Amineptine • Bemegride • BPAP • Clenbuterol • Clofenciclan • Cyclopentamine • Cyprodenate • Desoxypipradrol • Ethylphenidate • Ethamivan • Gilutensin • GYKI-52895 • Hexacyclonate • Indanorex • Indatraline • Isometheptene • Mazindol • MDPV • Mesocarb • Methylphenidate (Dexmethylphenidate) • Naphthylisopropylamine • Nikethamide • Nocaine • Nomifensine • Phacetoperane • Phthalimidopropiophenone • Pipradrol • Prolintane • Propylhexedrine • Pyrovalerone • Sibutramine • Tuamine • Vanoxerine • Yohimbine • Zylofuramine
See also Sympathomimetic amines

Categories: Tropanes | Dopamine reuptake inhibitors | Stimulants | Sympathomimetic amines

This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "RTI-121". A list of authors is available in Wikipedia.

Topics A-Z