(1R,2S,6R,7S)-4-{4-[4-(pyrimidin-2-yl)piperazin-1-yl]butyl}-4-azatricyclo[5.2.1.02,6]decane-3,5-dione

• ChemBase ID: 154461
• Molecular Formular: C21H29N5O2
• Molecular Mass: 383.48726
• Monoisotopic Mass: 383.23212519
• SMILES: c1cnc(nc1)N1CCN(CC1)CCCCN1C(=O)[C@H]2[C@@H]3CC[C@@H](C3)[C@H]2C1=O
• Canonical SMILES: O=C1N(CCCCN2CCN(CC2)c2ncccn2)C(=O)[C@@H]2[C@H]1[C@H]1CC[C@@H]2C1
• InChI: InChI=1S/C21H29N5O2/c27-19-17-15-4-5-16(14-15)18(17)20(28)26(19)9-2-1-8-24-10-12-25(13-11-24)21-22-6-3-7-23-21/h3,6-7,15-18H,1-2,4-5,8-14H2/t15-,16+,17+,18-
• InChIKey: CEIJFEGBUDEYSX-FZDBZEDMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,6R,7S)-4-{4-[4-(pyrimidin-2-yl)piperazin-1-yl]butyl}-4-azatricyclo[5.2.1.0^2,^6]decane-3,5-dione
• IUPAC Traditional name: tandospirone
• Synonyms: (1R*,2S*,3R*,4S*)-N-(4-(4-(2-Pyrimidinyl)-1-piperazinyl)butyl)-2,3-norbornanedicarboximide citrate salt; SM 3997; Tandospirone

Database IDs

• CAS Number: 87760-53-0
• PubChem SID: 162248600
• PubChem CID: 91273

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): -0.609466
• LogD (pH = 7.4): 1.0718763
• Log P: 1.4968145
• Molar Refractivity: 107.1089 cm^3
• Polarizability: 40.89443 Å^3
• Polar Surface Area: 69.64 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble38 mg/mL

Safety Information

• Storage Condition: protect from light
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C21H29N5O2

DETAILS

Sigma Aldrich - T6704

Biochem/physiol Actions
Tandospirone is a partial agonist at 5HT1A receptors. It significantly reduces haloperidol-induced bradykinesia in a dose-dependent manner. The potency of tandospirone is equal to that of buspirone and approximate half that of diazepam. The potency of tandospirone as a dopamine antagonistic is less than 1/4 that of buspirone.