6H-Dibenzo[a,g]quinolizine, 5,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-, (13aS)-
rotundine
CAS: 483-14-7
Molecular Formula: C21H25NO4
6H-Dibenzo[a,g]quinolizine, 5,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-, (13aS)- - Names and Identifiers
6H-Dibenzo[a,g]quinolizine, 5,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-, (13aS)- - Physico-chemical Properties
| Molecular Formula | C21H25NO4 |
| Molar Mass | 355.43 |
| Density | 1.23±0.1 g/cm3(Predicted) |
| Melting Point | 141-143°C |
| Boling Point | 482.9±45.0 °C(Predicted) |
| Solubility | insoluble in H2O; ≥16 mg/mL in DMSO; ≥2.95 mg/mL in EtOH with gentle warming and ultrasonic |
| Appearance | powder to crystal |
| Color | White to Light yellow |
| Maximum wavelength(λmax) | ['280nm(lit.)'] |
| pKa | 6.53±0.20(Predicted) |
| Storage Condition | Sealed in dry,2-8°C |
| In vitro study | The affinity of Rotundine for dopamine D1 receptor is higher than that for dopamine D2 receptor, K I is 124 nM and 388 nM, and IC50 values are 166 nM (D1) and 1.47 μm (D2), respectively. Rotundine exhibited a weak inhibitory activity on dopamine D3 with an IC50 value of 3.25 μm. Rotundine was also effective in inhibiting 5-HT1A with an IC50 of 374 nM and a K I of 340 nM. In addition to postsynaptic dopamine receptor antagonism, the inhibitory effect of Rotundine on presynaptic autoreceptors leads to increased dopamine release, which may be due to the lower affinity of Rotundine for D2 receptors. In addition to dopamine receptors, Rotundine is able to interact with many other types of receptors, including Alpha -1 adrenergic receptors, which act as antagonists, and gamma aminobutyric acid receptors, which promote gamma aminobutyric acid binding through positive allosteric effects. |
| In vivo study | Treatment with Rotundine at 6.25 mg/kg, 12.5 mg/kg, or 18.75 mg/kg did not affect locomotor activity, but significantly antagonized oxycodone (5 mg/kg). Induced ADHD. Oral administration of Rotundine (10-25 mg/kg) significantly increased the hot plate latency in mice, indicating that Rotundine has significant analgesic activity, which is associated with beta endorphin neurons of the arcuate nucleus and spinal D2 receptors. Oral administration of Rotundine (1-10 mg/kg) dose-dependently increases fixed rate (FR) due to postsynaptic, rather than presynaptic, DA receptor blocking mechanisms the fortified cocaine self-administration rate, while the dose of 20 mg/kg will reduce it. In contrast to the cocaine effect, Rotundine produced inhibitory effects on sucrose self-administration and exercise only at doses of 10 mg/kg, but not 1 mg/kg or 3 mg/kg. LD50: Mouse 1160 mg/kg (Gavage) |
6H-Dibenzo[a,g]quinolizine, 5,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-, (13aS)- - Risk and Safety
| RTECS | HQ1792500 |
6H-Dibenzo[a,g]quinolizine, 5,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-, (13aS)- - References
| biological activity | Rotundine is a selective dopamine D1 receptor antagonist with an IC50 of 166 nM. |
| Target | Value |
| D1 receptor | 166 nM |
| 5-HT1A | 347 nM |
| D2 receptor | 1.47 μM |
| D3 receptor | 3.25 μM |
Last Update：2024-04-09 19:05:25
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Multiple SpecificationsSpot supply
Product Name: L-Tetrahydropalmatine Visit Supplier Webpage Request for quotationCAS: 483-14-7
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
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