(-)-2β-Carbomethoxy-3β-(4-iodophenyl)tropane

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IUPAC_name = methyl (1R,2S,3S,5S)-3-(4-iodophenyl)-8-methyl -8-azabicyclo [3.2.1] octane-2-carboxylate


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CAS_number = 133647-95-7
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PubChem = 108220
C=16 | H=20 | I=1 | N=1 | O=2
molecular_weight = 385.24 g/mol
smiles = CN1 [C@H] 2CC [C@@H] 1 [C@H] ( [C@H] (C2)C3=CC=C(C=C3)I)C(=O)OC
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legal_UK = Class A
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(-)-2β-Carbomethoxy-3β-(4-iodophenyl)tropane (β-CIT or RTI-55) is a stimulant drug used in scientific research and with some medical uses, which was developed in the early 1990s. [Boja JW, Patel A, Carroll FI, Rahman MA, Philip A, Lewin AH, Kopajtic TA, Kuhar MJ. [125I] RTI-55: a potent ligand for dopamine transporters. European Journal of Pharmacology. 1991 Feb 26;194(1):133-4.] β-CIT is a phenyltropane based dopamine reuptake inhibitor and is derived from methylecgonidine. β-CIT is one of the most potent phenyltropane stimulants that is commercially available, which limits its use in humans, as it might have significant abuse potential if used outside of a strictly controlled medical setting. [Weed MR, Mackevicius AS, Kebabian J, Woolverton WL. Reinforcing and discriminative stimulus effects of beta-CIT in rhesus monkeys. "Pharmacology, Biochemistry and Behaviour". 1995 Aug;51(4):953-6.] When radiolabeled with iodine-123, it is known as iometopane.

Uses

β-CIT is mainly used in scientific research into the dopamine reuptake transporter. Various radiolabelled forms of β-CIT (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 and serotonin transporters in the brain. [Cite journal
author = Shaya EK, Scheffel U, Dannals RF, Ricaurte GA, Carroll FI, Wagner HN Jr, Kuhar MJ, Wong DF
title = In vivo imaging of dopamine reuptake sites in the primate brain using single photon emission computed tomography (SPECT) and iodine-123 labeled RTI-55
journal = Synapse
year = 1992
month = February
volume = 10
issue = 2
pages = 169–172
doi = 10.1002/syn.890100210] [Cite journal
author = Shang Y, Gibbs MA, Marek GJ, Stiger T, Burstein AH, Marek K, Seibyl JP, Rogers JF
title = Displacement of serotonin and dopamine transporters by venlafaxine extended release capsule at steady state: a ¹²³I2beta-carbomethoxy-3beta-(4-iodophenyl)-tropane single photon emission computed tomography imaging study
journal = Journal of Clinical Psychopharmacology
year = 2007
monht = February
volume = 27
issue = 1
pages = 71–75
pmid = 17224717
url = http://www.psychopharmacology.com/pt/re/jclnpsychopharm/abstract.00004714-200702000-00014.htm
doi = 10.1097/JCP.0b013e31802e0017] The main practical application for this drug in medicine is to assess the rate of dopamine neuron degradation in the brains of sufferers of Parkinson's disease [Staffen W, Mair A, Unterrainer J, Trinka E, Bsteh C, Ladurner G. [123I] beta-CIT binding and SPET compared with clinical diagnosis in parkinsonism. Nuclear Medicine Communications. 2000 May;21(5):417-24.] [ Zubal IG, Early M, Yuan O, Jennings D, Marek K, Seibyl JP. Optimized, automated striatal uptake analysis applied to SPECT brain scans of Parkinson's disease patients. Journal of Nuclear Medicine. 2007 Jun;48(6):857-64. ] and some other conditions such as progressive supranuclear palsy. [Seppi K, Scherfler C, Donnemiller E, Virgolini I, Schocke MF, Goebel G, Mair KJ, Boesch S, Brenneis C, Wenning GK, Poewe W. Topography of dopamine transporter availability in progressive supranuclear palsy: a voxelwise [123I] beta-CIT SPECT analysis.Archives of Neurology. 2006 Aug;63(8):1154-60. ]

Legal Status

β-CIT is a Class A drug in the UK. [ [http://www.homeoffice.gov.uk/documents/cdlist.pdf?view=Binary Misuse of drugs list of drugs currently controlled under the misuse of drugs legislation. UK Home Office August 2008] ] Some other jurisdictions such as the USA, Canada, Australia and New Zealand might consider β-CIT to be a controlled substance analogue of cocaine on the grounds of its related chemical structure.

References