2,3-dihydroxybutanedioic acid methyl (1R,2S,3S,5S)-8-methyl-3-phenyl-8-azabicyclo[3.2.1]octane-2-carboxylate

• ChemBase ID: 134011
• Molecular Formular: C20H27NO8
• Molecular Mass: 409.43028
• Monoisotopic Mass: 409.17366683
• SMILES: CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)c1ccccc1)C(=O)OC.C(C(C(=O)O)O)(C(=O)O)O
• Canonical SMILES: OC(=O)C(C(C(=O)O)O)O.COC(=O)[C@@H]1[C@H]2CC[C@H](N2C)C[C@@H]1c1ccccc1
• InChI: InChI=1S/C16H21NO2.C4H6O6/c1-17-12-8-9-14(17)15(16(18)19-2)13(10-12)11-6-4-3-5-7-11;5-1(3(7)8)2(6)4(9)10/h3-7,12-15H,8-10H2,1-2H3;1-2,5-6H,(H,7,8)(H,9,10)/t12-,13+,14+,15-;/m0./s1
• InChIKey: WYGLYLVLBCZESH-PEVLCXCCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,3-dihydroxybutanedioic acid methyl (1R,2S,3S,5S)-8-methyl-3-phenyl-8-azabicyclo[3.2.1]octane-2-carboxylate
• IUPAC Traditional name: (.+-.)-tartaric acid; troparil
• Synonyms: β-CPT tartrate; (–)-2β-Carbomethoxy-3β-phenyltropane tartrate; Troparil tartrate; WIN 35,065-2; D-CPT tartrate

Database IDs

• CAS Number: 50372-80-0
• PubChem SID: 162228288
• PubChem CID: 21124918

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -0.80475134
• LogD (pH = 7.4): 0.6407752
• Log P: 2.5112362
• Molar Refractivity: 74.5101 cm^3
• Polarizability: 29.5783 Å^3
• Polar Surface Area: 29.54 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: ethanol: soluble; H2O: soluble
• Apperance: white solid
• Optical Rotation: [α]22/D -95.9°, c = 1.1 in H2O(lit.)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Drug Control: USDEA Schedule II; Home Office Schedule 2; regulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: -20°C

Product Information

• Purity: >94%

DETAILS

Sigma Aldrich - C156

Biochem/physiol Actions
Binds to the cocaine receptor site on the dopamine transporter and blocks dopamine uptake.
Caution
Hygroscopic