(1R*,2S*,3R*,4S*)-N-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-2,3-bicyclo[2.2.1]heptanedicarboximide
tandospirone
CAS: 87760-53-0
Molecular Formula: C21H29N5O2
(1R*,2S*,3R*,4S*)-N-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-2,3-bicyclo[2.2.1]heptanedicarboximide - Names and Identifiers
(1R*,2S*,3R*,4S*)-N-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-2,3-bicyclo[2.2.1]heptanedicarboximide - Physico-chemical Properties
| Molecular Formula | C21H29N5O2 |
| Molar Mass | 383.49 |
| Density | 1.239±0.06 g/cm3(Predicted) |
| Melting Point | 112-113.5° |
| Boling Point | 613.9±65.0 °C(Predicted) |
| Flash Point | 325.1°C |
| Solubility | DMSO: soluble38mg/mL |
| Vapor Presure | 5.23E-15mmHg at 25°C |
| Appearance | Solid |
| Color | White to Off-White |
| pKa | 7.71±0.10(Predicted) |
| Storage Condition | Store at +4°C |
| Refractive Index | 1.589 |
| Physical and Chemical Properties | Crystallized from toluene-n-hexane, melting point 112-113.5 °c. Tandospirone Citrate: C2Lh29N5O2? C6H8O7. [112457-95-1]. Tandospirone Hydrochloride: C2lH29N5O2? HCl. Crystallization from isopropanol, melting point 227-229 °c. |
| In vitro study | Tandospirone is approximately two to three orders of magnitude less potent at 5-HT 2 , 5-HT 1C , α1-adrenergic, α2-adrenergic and dopamine D1 and D2 receptors (K i values ranging from 1300 to 41000 nM) than 5-HT 1A . Tandospirone is essentially inactive at 5-HT 1B receptors; 5-HT uptake sites; beta-adrenergic, muscarinic cholinergic, and benzodiazepine receptors. Tandospirone activats postsynaptic 5-HT 1A receptor coupled with G-protein (G i/o ), resulting in inhibition of protein kinase A (PKA)-mediated protein phosphorylation and neuronal activity. |
(1R*,2S*,3R*,4S*)-N-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-2,3-bicyclo[2.2.1]heptanedicarboximide - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 3 |
(1R*,2S*,3R*,4S*)-N-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-2,3-bicyclo[2.2.1]heptanedicarboximide - Preparation solution concentration reference
| 1mg | 5mg | 10mg | |
|---|---|---|---|
| 1 mM | 2.608 ml | 13.038 ml | 26.076 ml |
| 5 mM | 0.522 ml | 2.608 ml | 5.215 ml |
| 10 mM | 0.261 ml | 1.304 ml | 2.608 ml |
| 5 mM | 0.052 ml | 0.261 ml | 0.522 ml |
Last Update：2024-01-02 23:10:35
(1R*,2S*,3R*,4S*)-N-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-2,3-bicyclo[2.2.1]heptanedicarboximide - Reference Information
| Introduction | tandospirone belongs to the class of azapirone, tandospirone has a clear anti-Anxiety effect, but also has a certain antidepressant effect, it is more selective than BDZ drugs, reduce the common adverse reactions of BDZ drugs. |
| Use | tandospirone (tandospirone) can selectively activate 5-HT1A receptors in the limbic system, without sedation, no sleep induction, no anticonvulsant effect, no muscle relaxation effect, no dependent effect. The drug is mainly used in clinical treatment of extensive Anxiety, such as Anxiety of patients with hypertension, Anxiety of patients with irritable bowel syndrome and Anxiety of patients with chronic obstructive pulmonary disease (COPD). 5HT1A partial agonist. For the treatment of depression. |
| adverse reactions | 1.5-HT1A receptor agonism (1) impaired verbal memory activation of 5-HT1A receptor in bilateral hippocampal postsynaptic membrane → activation of G protein → opening influx of K + channels → K + influx → neuronal inhibition, impaired clear verbal memory. (2) Sleep Initiation and Maintenance Disorders tandospirone activates 5-HT1A receptors on the presynaptic membrane of GABA neurons in the basal ganglia of the amygdala and inhibits GABA release, can cause Sleep Initiation and Maintenance Disorders (0.1% ~ 1%) and nightmares (<1%). (3) hypotensive tandospirone activates 5-HT receptor, which has a central hypotensive effect. When lowering blood pressure, it expands blood vessels, which can make plasma components penetrate into tissue spaces and cause edema, edema and compression of nerve endings, can cause numbness of limbs. (4) hyperprolactinemia tandospirone stimulates 5-HT1A receptors, thereby stimulating prolactin secretion. Tandospirone has been reported to cause gynecomastia. 2. Inhibition of monoamine oxidase tandospirone inhibits monoamine oxidase, resulting in blocked monoamine metabolism, resulting in increased synaptic levels of monoamines (including 5-HT, NE, and DA), high levels of monoamine can cause a series of adverse reactions. (1) the energy efficiency of 5-HT should be increased when the synaptic 5-HT can cause extrapyramidal response, Nausea, anorexia and Diarrhea. (2) pseudo-NE energy efficiency should increase the level of synaptic NE, similar to sympathetic excitation, in the nervous system can cause Sleep Initiation and Maintenance Disorders, nightmares, Head Pain (0.1% ~ 1%), dizziness (0.1% ~ 1%), dizziness and tremor (<1%); In the digestive system can cause dry mouth, Nausea (0.9%), anorexia (0.7%), bloating, abdominal distension and constipation, in the cardiovascular system can cause palpitations, tachycardia (0.1% ~ 1%) and sweating (sweating or night sweats); And due to increased metabolism caused by the chest red and burning sensation. 3. Weak anti-DA effect tandospirone has weak anti-DA effect, which may cause parkinsonian symptoms. If intercostal muscle tone increases, it may explain chest tightness (0.1% ~ 1%).. Tandospirone combined with haloperidol may enhance extrapyramidal reactions. |
| biological activity | tandosprone (SM-3997) is a potent and selective partial agonist of the 5-HT1A receptor, its Ki value is 27 nM. Tandosprone has an anti-Anxiety and anti-depressant effect. Tandosprone can be used in the study of central nervous system diseases and their potential mechanisms. |
| Animal Model: | Seven-week-old male Sprague-Dawley rats (260-300 g), conditioned fear stress-induced freezing behavior rat model |
| Dosage: | 10 mg/kg, 20 mg/kg, 40 mg/kg, 80 mg/kg |
| Administration: | Intraperitoneal injection |
| Result: | Inhibited freezing behavior in a dose-dependent manner. |
| production method | borneane and 1-(4-aminobutyl)-4-(2-pyrimidinyl) the product was obtained by piperazine reaction. |
Last Update：2024-04-09 21:50:46
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