SKF 83959 , CAS No.80751-85-5

CAS: 80751-85-5 Cat. No.: S647497 Molecular Weight: 317.8 PubChem CID: 133538
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Synonyms
J489.412J | CHEBI:64001 | NCGC00015940-03 | 9-chloro-3-methyl-5-(3-methylphenyl)-1,2,4,5-tetrahydro-3-benzazepine-7,8-diol | Bio2_000839 | Diphenyl-propoxyessigsaeure-1-methylpiperidin-4-ylester | SKF-83,959 | 6-chloro-3-methyl-1-(3-methylphenyl)-2,3,4,5-
Storage
Store at -20°C
Shipped In
Ice chest + Ice pads
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Size
Status
Price
Qty
5mg
S647497-5mg
8-12 wks(?) Production requires sourcing of materials. We appreciate your patience and understanding.
$380.90
10mg
S647497-10mg
8-12 wks(?) Production requires sourcing of materials. We appreciate your patience and understanding.
$600.90
25mg
S647497-25mg
8-12 wks(?) Production requires sourcing of materials. We appreciate your patience and understanding.
$1,200.90
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Why this grade

for sensitive chromatographic and analytical workflows requiring minimal baseline interference.

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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.

Overview

SKF83959 is a potent and selective dopamine D 1 -like receptor partial agonist. SKF83959 K i values for rat D 1 , D 5 , D 2 and D 3 receptors are 1.18, 7.56, 920 and 399 nM, respectively. SKF83959 is a potent allosteric modulator of sigma (σ)-1 receptor. SKF83959 belongs to benzazepine family and has improvements on cognitive dysfunction. SKF83959 can be used for the research of Alzheimer's disease and depression.

In Vitro

SKF83959 (10~250 μM) stimulates PIP2 hydrolysis in membranes. SKF83959 (0.1~10 μM; PC12 cell) changes the EC 50 value of SKF81297 from 0.5 nM in control tissue to 31.6 nM, 251.2 nM and 631.0 nM. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

SKF83959 (0.5 and 1 mg/kg; i.p.; 1 hour) reverses the scopolamine-induced cognitive impairments in the passive avoidance task and Y-Maze test . SKF83959 (1 mg/kg; i.p.; 30 minutes) induced memory enhancing effects are prevented by brain-derived neurotrophic factor system blockade . SKF83959 has anti-amnesic activities and restores the scopolamine-decreased BDNF signaling pathway in the hippocampus in mice . MCE has not independently confirmed the accuracy of these methods. They are for reference only. Animal Model: Male ICR male mice (8 weeks) Dosage: 0.5 and 1 mg/kg Administration: I.p.; 1 hour Result: Reversed the scopolamine-induced cognitive impairments in the passive avoidance task and Y-Maze test. Animal Model: Male ICR male mice (8 weeks) Dosage: 1 mg/kg Administration: I.p.; 30 minutes Result: The memory enhancing effects were prevented by BDNF system blockade.

Form:Solid

Specifications

Synonyms
J489.412J | CHEBI:64001 | NCGC00015940-03 | 9-chloro-3-methyl-5-(3-methylphenyl)-1, 2, 4, 5-tetrahydro-3-benzazepine-7, 8-diol | Bio2_000839 | Diphenyl-propoxyessigsaeure-1-methylpiperidin-4-ylester | SKF-83, 959 | 6-chloro-3-methyl-1-(3-methylphenyl)-2, 3, 4, 5-
Biochemical and Physiological Mechanisms
SKF83959 is a potent and selective dopamine D 1 -like receptor partial agonist. SKF83959 K i values for rat D 1 , D 5 , D 2 and D 3 receptors are 1.18, 7.56, 920 and 399 nM, respectively. SKF83959 is a potent allosteric modulator of sigma (σ)-1 receptor.
Storage
Store at -20°C
Shipped In
Ice chest + Ice pads
This product requires cold chain shipping. Ground and other economy services are not available.
Names and Identifiers
Canonical SmilesCC1=CC(=CC=C1)C2CN(CCC3=C(C(=C(C=C23)O)O)Cl)C
IUPAC Name9-chloro-3-methyl-5-(3-methylphenyl)-1,2,4,5-tetrahydro-3-benzazepine-7,8-diol
InChIKeyJXMYTVOBSFOHAF-UHFFFAOYSA-N
INCHI1S/C18H20ClNO2/c1-11-4-3-5-12(8-11)15-10-20(2)7-6-13-14(15)9-16(21)18(22)17(13)19/h3-5,8-9,15,21-22H,6-7,10H2,1-2H3
Isomeric SMILES CC1=CC(=CC=C1)C2CN(CCC3=C(C(=C(C=C23)O)O)Cl)C
WGK Germany 3
PubChem CID 133538
Molecular Weight 317.8

Documentation

📋 Safety Data Sheet (SDS)

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

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✅ Certificate of Analysis (COA)

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

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📊 Datasheet

Quick-reference summary of product specifications and applications.

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🔬 Specification Sheet

Full quality attributes and acceptance criteria for this grade.

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Advanced Data

Taxonomic Classification

Taxonomy Tree

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassBenzazepines
SubclassNot available
Intermediate Tree Nodes Not available
Direct ParentBenzazepines
Alternative Parents Toluenes  Azepines  Aralkylamines  1-hydroxy-2-unsubstituted benzenoids  Aryl chlorides  Trialkylamines  Azacyclic compounds  Organopnictogen compounds  Organooxygen compounds  Organochlorides  Hydrocarbon derivatives  
Molecular FrameworkAromatic heteropolycyclic compounds
Substituents Benzazepine - 1-hydroxy-2-unsubstituted benzenoid - Azepine - Aralkylamine - Toluene - Aryl chloride - Aryl halide - Monocyclic benzene moiety - Benzenoid - Tertiary amine - Tertiary aliphatic amine - Azacycle - Organooxygen compound - Organonitrogen compound - Organochloride - Organohalogen compound - Hydrocarbon derivative - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Amine - Aromatic heteropolycyclic compound
DescriptionThis 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 tertiary amino compound - organochlorine compound - catechols - benzazepine
3D Structure
Interactive Chemical Structure Model





Associated Targets(Human)
DRD1 Tclin D(1A) dopamine receptor (0 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
Certificates(CoA,COO,BSE/TSE and Analysis Chart)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemical and Physical Properties
SolubilityDMSO : ≥ 100 mg/mL (314.65 mM)
Molecular Weight317.800 g/mol
XLogP33.600
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count1
Exact Mass317.118 Da
Monoisotopic Mass317.118 Da
Topological Polar Surface Area43.700 Ų
Heavy Atom Count22
Formal Charge0
Complexity380.000
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
Solution Calculators
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