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

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-26-36

WGK Germany 

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.

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.

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