155797-99-2

Basic information

• Product Name: 8-AZABICYCLO[3.2.1]OCTANE-2-CARBOXYLIC ACID, 8-(3-FLUOROPROPYL)-3-(4-IODOPHENYL)-, METHYL ESTER (1R,2S,3S,5S)-
• Synonyms: 8-AZABICYCLO[3.2.1]OCTANE-2-CARBOXYLIC ACID, 8-(3-FLUOROPROPYL)-3-(4-IODOPHENYL)-, METHYL ESTER (1R,2S,3S,5S)-;BETA-CIT-FP;CITFP;RTI 313;N-2-FLUOROPROPYL-3-BETA-(4-IODOPHENYL)NORTROPANE-2-BETA-CARBOXYLIC ACID METHYL ESTER;2-carbomethoxy-8-(3-fluoropropyl)-3-(4-iodophenyl)tropane;CITFP, beta-CIT-FP;8-Azabicyclo[3.2.1]octane-2-carboxylic acid, 8-(3-fluoropropyl)-3-(4-iodophenyl)-, methyl ester, (1R,2S,3S,5S)-
• CAS NO: 155797-99-2
• Molecular Formula: C₁₈H₂₃FINO₂
• Molecular Weight: 431.28
• Mol File: 155797-99-2.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 446.7 °C at 760 mmHg
• Flash Point: 224 °C
• Appearance: Colourless or yellowish crystal
• Density: 1.45 g/cm³
• Vapor Pressure: 3.57E-08mmHg at 25°C
• Refractive Index: 1.561
• CAS DataBase Reference: 8-AZABICYCLO[3.2.1]OCTANE-2-CARBOXYLIC ACID, 8-(3-FLUOROPROPYL)-3-(4-IODOPHENYL)-, METHYL ESTER (1R,2S,3S,5S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 8-AZABICYCLO[3.2.1]OCTANE-2-CARBOXYLIC ACID, 8-(3-FLUOROPROPYL)-3-(4-IODOPHENYL)-, METHYL ESTER (1R,2S,3S,5S)-(155797-99-2)
• EPA Substance Registry System: 8-AZABICYCLO[3.2.1]OCTANE-2-CARBOXYLIC ACID, 8-(3-FLUOROPROPYL)-3-(4-IODOPHENYL)-, METHYL ESTER (1R,2S,3S,5S)-(155797-99-2)

Safety Data

• Hazardous Substances Data: 155797-99-2(Hazardous Substances Data)

Usage

Chemical Properties

Colourless or yellowish crystals

Uses

CITFP is a cocaine analog used for the imaging of the dopamine transporter; Also, it is derived from (-)-2β-Carbomethoxy-3β-(4-iodophenyl)nortropane (C176610), which is an inhibitor of the serotonin (5-HT) transporter.

InChI:InChI=1/C18H23FINO2/c1-23-18(22)17-15(12-3-5-13(20)6-4-12)11-14-7-8-16(17)21(14)10-2-9-19/h3-6,14-17H,2,7-11H2,1H3/t14?,15-,16+,17+/m1/s1

Upstream product

• 462-43-1 3-fluoropropane-1-ol 
• 136794-87-1 (1R,2S,3S,5S)-3-(4-Iodo-phenyl)-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester 
• 462-40-8 1-fluoro-3-iodo-propane 
• 17878-43-2 [4-(trimethylsilyl)phenyl]magnesium bromide 
• 174224-35-2 2β-carbomethoxy-3β-(4'-trimethylsilylphenyl)tropane 
• 50373-10-9 methyl ecgonidine 
• 135416-43-2 (1R,2S,3S,5S)-3-(4-Iodo-phenyl)-8-methyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester 
• 352-91-0 1-Bromo-3-fluoropropane 

Downstream Products

• 199591-08-7 (1R,2S,3S,5S)-8-(3-Fluoro-propyl)-3-(4-iodo-3-nitro-phenyl)-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester 
• 172651-49-9 N-3-fluoropropyl-3-β-(4-iodophenyl)nortropane-2-β-carboxylic acid 

Relevant articles and documents

PROCESS FOR THE PREPARATION OF RADIOIODINATED 3-FLUOROPROPYL-NOR-Beta-CIT

The invention generally provides processes for the preparation of radioiodinated 3-fluoropropyl-nor-β-CIT. In particular, the process uses an arylsilane intermediate, thus avoiding the use of hexamethylditin, and reducing the number of steps previously required for the preparation of radioiodinated 3-fluoropropyl-nor-β-CIT from anhydroecgonine methyl ester. The invention also relates to the alkylation of a nortropane to the corresponding N-(3-fluoropropyl) analogue using 3-fluoropropanal.

Synthesis and biological evaluation of a series of novel N- or O-fluoroalkyl derivatives of tropane: Potential positron emission tomography (PET) imaging agents for the dopamine transporter

A series of novel fluoroalkyl-containing tropane derivatives was synthesized, and their binding affinities for the dopamine transporter (DAT), serotonin transporter (SERT), and norepinephrine transporter (NET) were determined via competitive binding assays. Among these derivatives, the fluoropropyl ester of β-CIT (19), the fluoroethyl ester of β-CIT (20), the N-fluoropropyl derivative of β-CBT (12), and the fluoropropyl ester of β-CMT (18) displayed higher affinity and greater selectivity for the DAT versus SERT and NET than FP-CIT, which indicates that they are attractive candidates for the development of 18F-labeled PET imaging agents for the DAT.