SKF-83566 - ≥99% , CAS No.99295-33-7

CAS: 99295-33-7 Cat. No.: S647449 Summenformel: C17H18BrNO Molekulargewicht: 332.23 PubChem CID: 1243
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GRADE & PURITY ≥99%
Synonyms
SKF-83566 | 8-bromo-2,3,4,5-tetrahydro-3-methyl-5-phenyl-1h-3-benzazepin-7-ol | SK83566 | SK-83566 | CHEBI:91747 | PDSP1_000503 | 8-Bromo-3-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ol | 8-Bromo-3-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-3-benza
Storage
Store at -20°C
Shipped In
Ice chest + Ice pads
★
Size
Deutschland (EU)
USA*
Price
Qty
5mg
S647449-5mg
Auf Bestellung · 8–12 Wochen
165,65€
10mg
S647449-10mg
Auf Bestellung · 8–12 Wochen
261,10€
25mg
S647449-25mg
Auf Bestellung · 8–12 Wochen
469,36€
Enter a quantity for the sizes you want to add.
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Why this grade

≥99% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.

🌡

Storage & shipping

Store at -20°C Ships Ice chest + Ice pads Check lot-specific COA for exact specifications.

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Quality documents

SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.

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Literature proof

Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.

Übersicht

SKF-83566 is a potent, blood-brain permeable and orally active D1-like dopamine receptor (D1DR) antagonist and a weaker competitive antagonist at the vascular 5-HT 2 receptor ( K i =11 nM) SKF-83566 is a competitive DAT (dopamine transporter) inhibitor with an IC 50 of 5.7 μM SKF-83566 also shows selective inhibition for adenylyl cyclase 2 (AC2) over AC 1 and AC 5 in the isolated rabbit thoracic aorta. SKF-83566 can be used for research of parkinson’s disease and nicotine craving alleviation.

In Vitro

SKF-83566 (0.1 μM-10 μM) causes a concentration-dependent increase in peak evoked extracellular DA concentration ([DA] o )?evoked by single-pulse stimulation, with a maximum 65% increase in peak evoked [DA] o with 5 μM. The EC 50 value of this effect of SKF-83566 is 1.3 μM. SKF-83566 inhibited [ 3 H]DA uptake with an IC 50 ?of 5.73 μM. Moreover, SKF-83566 more potently inhibits the binding of [ 3 H]CFT, with an IC 50 ?of 0.51 μM in [ 3 H]DA uptake and [ 3 H]CFT binding studies. Similarly, in LLc-PK-rDAT cell, SKF-83566 also inhibits [ 3 H]CFT binding with an IC 50 ?of 0.77 μM in LLc-PK-rDAT cell membrane preparations. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

SKF 83566 (oral administration; 20 μg/mL; 7 days) alone has no effects on altering LTP (115%). However, combinnation of SKF 83566 and nicotine significantly blocks the enhancement of long-term synaptic potentiation (LTP) induced by pretreatment with nicotine (SKF 83566+nicotine+cocaine, 120%; nicotine+cocaine, 143%) . MCE has not independently confirmed the accuracy of these methods. They are for reference only. Animal Model: Male C57BL6/J mice (6- to 9-wk-old) Dosage: 20 µg/mL (Together with nicotine for 7 d, followed by the injection of cocaine) Administration: Oral administration; 7 days Result: Blocked nicotine and cocaine-induced facilitation of LTP.

Form:Solid

IC50& Target:D 1 Receptor D 5 Receptor 5-HT 2 Receptor 11 nM (Ki)

Specifications

Synonyme
SKF-83566 | 8-bromo-2,3,4,5-tetrahydro-3-methyl-5-phenyl-1h-3-benzazepin-7-ol | SK83566 | SK-83566 | CHEBI:91747 | PDSP1_000503 | 8-Bromo-3-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ol | 8-Bromo-3-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-3-benza
Spezifikationen & Reinheit
≥99%
Biochemische und physiologische Mechanismen
SKF-83566 is a potent,xa0blood-brain permeable and orally active D1-like dopamine receptor (D1DR) antagonist and a weaker competitive antagonist at the vascular 5-HT 2 receptor ( K i =11 nM). SKF-83566 is a competitive DAT (dopamine transporter)
Storage
Store at -20°C
Verschickt in
Ice chest + Ice pads
Dieses Produkt erfordert Kühlkettenversand. Grundversand und andere Economy-Optionen sind nicht verfügbar.
Reinheit
≥99%
Namen und Kennungen
Kanonisches LächelnCN1CCC2=CC(=C(C=C2C(C1)C3=CC=CC=C3)O)Br
IUPAC Name8-bromo-3-methyl-5-phenyl-1,2,4,5-tetrahydro-3-benzazepin-7-ol
InChIKeyXFTVOHWWEQGXLS-UHFFFAOYSA-N
INCHI1S/C17H18BrNO/c1-19-8-7-13-9-16(18)17(20)10-14(13)15(11-19)12-5-3-2-4-6-12/h2-6,9-10,15,20H,7-8,11H2,1H3
Isomere SMILES CN1CCC2=CC(=C(C=C2C(C1)C3=CC=CC=C3)O)Br
Alternative CAS-Nummer 99295-33-7
PubChem CID 1243
MeSH-Eintrag 1H-3-benzazepin-7-ol, 8-bromo-2,3,4,5-tetrahydro-3-methyl-5-phenyl-;1H-3-benzazepin-7-ol, 8-bromo-2,3,4,5-tetrahydro-3-methyl-5-phenyl-, (S-isomer);7-bromo-8-hydroxy-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine;8-bromo-2,3,4,5-tetrahydro-3-methyl
Molekulargewicht 332.23

Documentation

📋 Safety Data Sheet (SDS)

Comprehensive hazard, handling, storage, and regulatory compliance document.

Download SDS →

✅ Certificate of Analysis (COA)

Lot-specific quality data. Enter your lot number to retrieve the exact COA.

Look up COA →

📊 Datasheet

Quick-reference summary of product specifications and applications.

View datasheet →

🔬 Specification Sheet

Full quality attributes and acceptance criteria for this grade.

View spec sheet →

Advanced Data

Taxonomic Classification

Taxonomy Tree

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
KlasseBenzazepines
SubclassNot available
Intermediate Tree Nodes Not available
Direct ParentBenzazepines
Alternative Parents O-bromophenols  Azepines  Aralkylamines  1-hydroxy-2-unsubstituted benzenoids  Benzene and substituted derivatives  Aryl bromides  Trialkylamines  Azacyclic compounds  Organopnictogen compounds  Organooxygen compounds  Organobromides  Hydrocarbon derivatives  
Molecular FrameworkAromatic heteropolycyclic compounds
Substituents Benzazepine - 2-bromophenol - 1-hydroxy-2-unsubstituted benzenoid - Azepine - Aralkylamine - Aryl bromide - Aryl halide - Monocyclic benzene moiety - Benzenoid - Tertiary aliphatic amine - Tertiary amine - Azacycle - Organobromide - Organohalogen compound - Organooxygen compound - Amine - Hydrocarbon derivative - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Organonitrogen compound - Aromatic heteropolycyclic compound
BeschreibungThis compound belongs to the class of organic compounds known as benzazepines. These are organic compounds containing a benzene ring fused to an azepine ring (unsaturated seven-membered heterocycle with one nitrogen atom replacing a carbon atom).
External Descriptors Not available
3D-Struktur
Interaktives chemisches Strukturmodell





Zugehörige Ziele (menschlich)
DRD1 Tclin D(1A) dopamine receptor (1 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
DRD5 Tchem D(1B) dopamine receptor (3 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
DRD2 Tclin Dopamine D2 receptor (23596 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DRD1 Tclin Dopamine D1 receptor (9720 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DRD5 Tchem Dopamine D5 receptor (1597 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADCY3 Tbio Adenylate cyclase type III (24 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADCY1 Tchem Brain adenylate cyclase 1 (372 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Zugehörige Ziele (nicht menschlich)
Adcy2 Adenylate cyclase type II (26 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Hdac6 Histone deacetylase 6 (222 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
J774.A1 (2436 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Wirkungsmechanismen
Zertifikate (CoA, COO, BSE/TSE und Analyse-Diagramm)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemische und physikalische Eigenschaften
LöslichkeitDMSO : 33.33 mg/mL (100.32 mM; Need ultrasonic)
Molekulargewicht332.200 g/mol
XLogP34.000
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count1
Exact Mass331.057 Da
Monoisotopic Mass331.057 Da
Topological Polar Surface Area23.500 Ų
Heavy Atom Count20
Formal Charge0
Complexity318.000
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
The total count of all stereochemical bonds0
Covalently-Bonded Unit Count1
Lösungsrechner
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