naphthalene-1,5-disulfonic acid hydrate methyl (1R,2S,3S,5S)-3-(4-fluorophenyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

• ChemBase ID: 132840
• Molecular Formular: C26H30FNO9S2
• Molecular Mass: 583.6461032
• Monoisotopic Mass: 583.13460177
• SMILES: CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)c1ccc(cc1)F)C(=O)OC.c1cc2c(cccc2S(=O)(=O)O)c(c1)S(=O)(=O)O.O
• Canonical SMILES: OS(=O)(=O)c1cccc2c1cccc2S(=O)(=O)O.COC(=O)[C@@H]1[C@H]2CC[C@H](N2C)C[C@@H]1c1ccc(cc1)F.O
• InChI: InChI=1S/C16H20FNO2.C10H8O6S2.H2O/c1-18-12-7-8-14(18)15(16(19)20-2)13(9-12)10-3-5-11(17)6-4-10;11-17(12,13)9-5-1-3-7-8(9)4-2-6-10(7)18(14,15)16;/h3-6,12-15H,7-9H2,1-2H3;1-6H,(H,11,12,13)(H,14,15,16);1H2/t12-,13+,14+,15-;;/m0../s1
• InChIKey: XSJPWVYASBDEJI-YEVYTSHMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: naphthalene-1,5-disulfonic acid hydrate methyl (1R,2S,3S,5S)-3-(4-fluorophenyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
• IUPAC Traditional name: 1,5-naphthalenedisulfonic acid hydrate methyl (1R,2S,3S,5S)-3-(4-fluorophenyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
• Synonyms: (-)-2-β-Carbomethoxy-3-β-(4-fluorophenyl)tropane 1,5-naphthalenedisulfonate monohydrate; WIN 35,428 naphthalenedisulfonate monohydrate; β-CFT naphthalenedisulfonate monohydrate

Database IDs

• CAS Number: 77210-32-3(anhydrous)
• MDL Number: MFCD11044874
• PubChem SID: 24892389; 162227117
• PubChem CID: 71308601

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -0.6060624
• LogD (pH = 7.4): 0.92327166
• Log P: 2.6539383
• Molar Refractivity: 74.7265 cm^3
• Polarizability: 29.23892 Å^3
• Polar Surface Area: 29.54 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble
• Apperance: white solid
• Optical Rotation: [α]25/D -62.5°, c = 1.0 in H2O(lit.)

Safety Information

• European Hazard Symbols: Highly toxic (T+)
• UN Number: 1544
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1
• Risk Statements: 26/27/28-43-62
• Safety Statements: 22-26-36/37/39-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H317-H330-H361
• GHS Precautionary statements: P260-P264-P280-P284-P301 + P310-P302 + P350
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 1544 6.1/PG 1
• Drug Control: USDEA Schedule II
• Storage Temperature: 2-8°C

DETAILS

Sigma Aldrich - C124

Biochem/physiol Actions
Cocaine analog that inhibits the dopamine, norepinephrine, and serotonin transporters with Kis of 26.1 nM, 31.9 nM, and 127 nM, respectively. [11C]-β-CFT and [18F]-β-CFT are ligands for PET imaging of the dopamine transporter in vivo.