ChemicalBook > CAS DataBase List > 2-phenyl-4-azabicyclo[5.4.0]undeca-7,9,11-triene-9,10-diol

2-phenyl-4-azabicyclo[5.4.0]undeca-7,9,11-triene-9,10-diol

Product Name: 2-phenyl-4-azabicyclo[5.4.0]undeca-7,9,11-triene-9,10-diol
CAS No.: 62717-42-4
Chemical Name: 2-phenyl-4-azabicyclo[5.4.0]undeca-7,9,11-triene-9,10-diol
Synonyms: Nsc320959;SKF-38393A;SKF38393 HCl ，S7993;SKF-38393A·hydrochloride;(±)-SKF-38393 hydrochloride;SKF 38393 hydrochloride, 10 mM in DMSO;(+/-)-SKF-38393 Hydrochloride, Crystalline;5-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-diol;2-phenyl-4-azabicyclo[5.4.0]undeca-7,9,11-triene-9,10-diol;(±)-SKF38393 hydrochloride, D1-like dopamine receptor agonist
CBNumber: CB31456599
Molecular Formula: C16H17NO2
Formula Weight: 0
MOL File: 62717-42-4.mol

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2-phenyl-4-azabicyclo[5.4.0]undeca-7,9,11-triene-9,10-diol Property

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)

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Safety

Hazard Codes: Xi
Risk Statements: 36/37/38
Safety Statements: 22-26-36
WGK Germany: 3

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: D047
Product name: (±)-SKF-38393 hydrochloride
Purity: crystalline, ≥98% (HPLC)
Packaging: 100mg
Price: $227
Updated: 2025/07/31

Sigma-Aldrich

Product number: D047
Product name: (±)-SKF-38393 hydrochloride
Purity: crystalline, ≥98% (HPLC)
Packaging: 1g
Price: $1360
Updated: 2025/07/31

Sigma-Aldrich

Product number: D047
Product name: (±)-SKF-38393 hydrochloride
Purity: crystalline, ≥98% (HPLC)
Packaging: 500mg
Price: $901
Updated: 2025/07/31

TRC

Product number: S550010
Product name: SKF38393Hydrochloride
Packaging: 250mg
Price: $185
Updated: 2021/12/16

ChemScene

Product number: CS-5354
Product name: SKF38393(hydrochloride)
Purity: 99.44%
Packaging: 50mg
Price: $78
Updated: 2021/12/16

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2-phenyl-4-azabicyclo[5.4.0]undeca-7,9,11-triene-9,10-diol Chemical Properties,Usage,Production

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

Raw materials

Preparation Products

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62717-42-4, 2-phenyl-4-azabicyclo[5.4.0]undeca-7,9,11-triene-9,10-diolRelated Search:

Bromocriptine mesylate BTCP HCL (+)-AJ 76 HYDROCHLORIDE R-(-)-7-Chloro-8-hydroxy-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine, hydrochloride LE 300 U-99194 MALEATE 6-Chloro-2,3,4,5-tetrahydro-7,8-dimethoxy-1-(4-methoxyphenyl)-1H-3-benzazepine Fenoldopam (+/-)-6-CHLORO-7,8-DIHYDROXY-3-ALLYL-1-PHENYL-2,3,4,5-TETRAHYDRO-1H-3-BENZAZEPINE HYDROBROMIDE 6-CHLORO-2,3,4,5-TETRAHYDRO-1-(3-METHYLPHENYL)-3-(2-PROPENYL)-1H-3-BENZAZEPINE-7,8-DIOL HYDROBROMIDE R(+)-6-CHLORO-7,8-DIHYDROXY-1-PHENYL-2,3,4,5-TETRAHYDRO-1H-3-BENZAZEPINE HYDROBROMIDE SKF 83959 HYDROBROMIDE 2-phenyl-4-azabicyclo[5.4.0]undeca-7,9,11-triene-9,10-diol (+/-)-6-CHLORO-7,8-DIHYDROXY-1-PHENYL-2,3,4,5-TETRAHYDRO-1H-3-BENZAZEPINE HYDROBROMIDE R(+)-6-CHLORO-7,8-DIHYDROXY-3-METHYL-1-PHENYL-2,3,4,5-TETRAHYDRO-1H-3-BENZAZEPINE HYDROBROMIDE (R)-6-CHLORO-2,3,4,5-TETRAHYDRO-1-(4-HYDROXYPHENYL)-1H-3-BENZAZEPINE-7,8-DIOL BROMIDE R(+)-SKF-38393 HYDROCHLORIDE S-(-)-SKF-38393 HCL

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

SKF 38393,SKF-38393,SKF 38393 hydrochloride,inhibit,Inhibitor,SKF38393,Dopamine Receptor

(±)-SKF38393 hydrochloride, D1-like dopamine receptor agonist

SKF 38393 hydrochloride, 10 mM in DMSO

(±)-SKF-38393 hydrochloride

(±)-SKF38393 hydrochloride, D1-like dopamine receptor agonist

SKF38393 HCl ，S7993

62717-42-4

Dopamine receptor

API