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

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(-)-2β-Carbomethoxy-3β-(4-iodophenyl)tropane
Legal status
Legal status	In general: legal;
Identifiers
	IUPAC name methyl (1R,2S,3S,5S)-3-(4-iodophenyl)-8-methyl -8-azabicyclo[3.2.1]octane-2-carboxylate;
CAS Number	133647-95-7;
PubChem CID	108220;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C16H20INO2
Molar mass	385.24 g/mol
3D model (JSmol)	Interactive image;
	SMILES CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)C3=CC=C(C=C3)I)C(=O)OC;

(-)-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.^[1] 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.^[2] 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.^[3]^[4] 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^[5]^[6] and some other conditions such as progressive supranuclear palsy.^[7]

Legal Status

β-CIT 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 β-CIT to be a controlled substance analogue of cocaine on the grounds of its related chemical structure.

References

↑ 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.
↑ 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.
↑ Shaya EK, Scheffel U, Dannals RF, Ricaurte GA, Carroll FI, Wagner HN Jr, Kuhar MJ, Wong DF (1992). "In vivo imaging of dopamine reuptake sites in the primate brain using single photon emission computed tomography (SPECT) and iodine-123 labeled RTI-55". Synapse. 10 (2): 169–172. doi:10.1002/syn.890100210. Unknown parameter |month= ignored (help)
↑ Shang Y, Gibbs MA, Marek GJ, Stiger T, Burstein AH, Marek K, Seibyl JP, Rogers JF (2007). "Displacement of serotonin and dopamine transporters by venlafaxine extended release capsule at steady state: a [¹²³I]2beta-carbomethoxy-3beta-(4-iodophenyl)-tropane single photon emission computed tomography imaging study". Journal of Clinical Psychopharmacology. 27 (1): 71–75. PMID 17224717. Unknown parameter |monht= ignored (help)
↑ 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.
↑ 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.

Template:Stimulants

Template:WikiDoc Sources

[1] 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.

[2] 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.

[3] Shaya EK, Scheffel U, Dannals RF, Ricaurte GA, Carroll FI, Wagner HN Jr, Kuhar MJ, Wong DF (1992). "In vivo imaging of dopamine reuptake sites in the primate brain using single photon emission computed tomography (SPECT) and iodine-123 labeled RTI-55". Synapse. 10 (2): 169–172. doi:10.1002/syn.890100210. Unknown parameter |month= ignored (help)

[4] Shang Y, Gibbs MA, Marek GJ, Stiger T, Burstein AH, Marek K, Seibyl JP, Rogers JF (2007). "Displacement of serotonin and dopamine transporters by venlafaxine extended release capsule at steady state: a [¹²³I]2beta-carbomethoxy-3beta-(4-iodophenyl)-tropane single photon emission computed tomography imaging study". Journal of Clinical Psychopharmacology. 27 (1): 71–75. PMID 17224717. Unknown parameter |monht= ignored (help)

[5] 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.

[6] 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.

[7] 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.

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Legal status

Legal status	In general: legal
Identifiers
IUPAC name methyl (1R,2S,3S,5S)-3-(4-iodophenyl)-8-methyl -8-azabicyclo[3.2.1]octane-2-carboxylate
CAS Number	133647-95-7
PubChem CID	108220
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C₁₆H₂₀INO₂
Molar mass	385.24 g/mol
3D model (JSmol)	Interactive image
SMILES CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)C3=CC=C(C=C3)I)C(=O)OC

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

Uses

Legal Status

References

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