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| | 2-phenyl-4-azabicyclo[5.4.0]undeca-7,9,11-triene-9,10-diol Basic information |
| Product Name: | 2-phenyl-4-azabicyclo[5.4.0]undeca-7,9,11-triene-9,10-diol | | Synonyms: | 2-phenyl-4-azabicyclo[5.4.0]undeca-7,9,11-triene-9,10-diol;SKF-38393A;SKF-38393A·hydrochloride;Nsc320959;(+/-)-SKF-38393 Hydrochloride, Crystalline;1-Phenyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine-7,8-diol hydrochloride;SKF 38393 HYDROCHLORIDE;(±)-SKF-38393 HYDROCHLORIDE;SKF-38393;5-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-diol | | CAS: | 62717-42-4 | | MF: | C16H17NO2 | | MW: | 0 | | EINECS: | | | Product Categories: | Dopamine receptor;API | | Mol File: | 62717-42-4.mol | ![2-phenyl-4-azabicyclo[5.4.0]undeca-7,9,11-triene-9,10-diol Structure](CAS/GIF/62717-42-4.gif) |
| | 2-phenyl-4-azabicyclo[5.4.0]undeca-7,9,11-triene-9,10-diol Chemical Properties |
| Melting point | 283-285 °C | | storage temp. | Keep in dark place,Inert atmosphere,Room temperature | | solubility | H2O: >5mg/mL | | form | crystalline | | color | white | | Water Solubility | H2O: >5mg/mL
aqueous base: soluble (unstable) | | InChI | 1S/C16H17NO2.ClH/c18-15-8-12-6-7-17-10-14(13(12)9-16(15)19)11-4-2-1-3-5-11;/h1-5,8-9,14,17-19H,6-7,10H2;1H | | InChIKey | YEWHJCLOUYPAOH-UHFFFAOYSA-N | | SMILES | Cl.Oc1cc2CCNCC(c3ccccc3)c2cc1O |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 22-26-36 | | WGK Germany | 3 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 2-phenyl-4-azabicyclo[5.4.0]undeca-7,9,11-triene-9,10-diol Usage And Synthesis |
| Uses | SKF 38393 Hydrochloride is a D1 receptor agonist. | | Biological Activity | skf38393 hcl (skf38393) is a selective dopamine d1 receptor agonist [1], with an ic50 value of 110 nm [2].there are two functional types of dopamine receptors, d1 and d2 receptors [3]. the stimulation of the d1 receptor (d1r) in prefrontal cortex (pfc) results in an ‘inverted-u’ dose-response. either too little or too much d1r stimulation can impair spatial working memory [4].6-ohda reduced the specific expression of mrnas to encode substance p and d1 dopamine receptor in striatonigral neurons. subsequently daily injections of skf-38393 reversed this reduction effect. the treatment with skf-38393 also increased dynorphin mrna [5]. d1rs activate cyclic amp-dependent protein kinases, stimulate adenylyl cyclase, regulate neuron growth and differentiation, modify dopamine d2 receptor-mediated events and influence behavior [3]. in a 96-well plate assay, the plating of mcf-7 cells was involved in the breast cancer in vitro screening procedure. after 1 day, treatment with skf 38393 was applied to cells for 2 days. data showed that skf 38393 significantly decrease the proliferation of mcf-7 cells. the ic50 value was 0.1 +/- 0.03 μm [6].in locally anesthetized, artificially respired, gallamine-treated rats, i.v. administration of skf 38393 significantly altered dopamine cell activity. in these rats, firing rate increases and decreases were also observed [7]. | | Biochem/physiol Actions | (±)-SKF-38393 is a D1 dopamine receptor agonist. It is known to promote the production of glutamate in the hippocampus. | | in vivo | SKF-38393 hydrochloride (10 mg/kg; i.p.) blocks the 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) -induced depletion of glutathione[3].
SKF-38393 hydrochloride attenuates MPTP-induced depletion of dopamine[3].
SKF-38393 hydrochloride enhances the activity of superoxide dismutase and hence mimics the action of Selegiline[3].
SKF-38393 hydrochloride enhances the frequency but not the amplitude of tetrodotoxin-resistant excitatory postsynaptic currents which argues for a presynaptic locus of D1 action[4].
| Animal Model: | Balb/c mice ( 20-25 g)[3].
| | Dosage: | 5 mg/kg, 10 mg/kg | | Administration: | Intraperitoneal injection | | Result: | Blocked the MPTP-induced depletion of glutathione and attenuated MPTP-induced depletion of dopamine. |
| | IC 50 | D1 Receptor | | storage | -20°C (desiccate) | | references | [1]. rimondini r, ferré s, giménez-llort l, et al. differential effects of selective adenosine a1 and a2a receptor agonists on dopamine receptor agonist-induced behavioral responses in rats. european journal of pharmacology, 1998, 347(2): 153-158.
[2]. altar ca, marien mr. picomolar affinity of 125i-sch 23982 for d1 receptors in brain demonstrated with digital subtraction autoradiography. the journal of neuroscience, 1987, 7(1): 213-222.
[3]. sunahara rk, niznik hb, weiner dm, et al. human dopamine d1 receptor encoded by an intronless gene on chromosome 5. 1990, 347:80-83.
[4]. vijayraghavan s, wang m, birnbaum sg, et al. inverted-u dopamine d1 receptor actions on prefrontal neurons engaged in working memory. nature neuroscience, 2007, 10(3): 376-384.
[5]. gerfen cr, engber tm, mahan lc, et al. d1 and d2 dopamine receptor-regulated gene expression of striatonigral and striatopallidal neurons. science, 1990, 250(4986): 1429-1432.
[6]. johnson de, ochieng j, evans sl. the growth inhibitory properties of a dopamine agonist (skf 38393) on mcf-7 cells. anti-cancer drugs, 1995, 6(3): 471-474.
[7]. carlson jh, bergstrom da, weick bg, et al. neurophysiological investigation of effects of the d-1 agonist skf 38393 on tonic activity of substantia nigra dopamine neurons. synapse, 1987, 1(5): 411-416. |
| | 2-phenyl-4-azabicyclo[5.4.0]undeca-7,9,11-triene-9,10-diol Preparation Products And Raw materials |
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