SKF-83822 HBr | CAS# 74115-10-9 | Dopamine D1-like receptor agonist

MedKoo Cat#: 574408 | Name: SKF-83822 HBr

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

SKF-83822 HBr is a selective dopamine D1-like receptor agonist that stimulates adenylyl cyclase but not phosphoinositide hydrolysis.

Chemical Structure

SKF-83822 HBr

CAS#74115-10-9

Theoretical Analysis

MedKoo Cat#: 574408

Name: SKF-83822 HBr

CAS#: 74115-10-9

Chemical Formula: C20H23BrClNO2

Exact Mass: 0.0000

Molecular Weight: 424.76

Elemental Analysis: C, 56.55; H, 5.46; Br, 18.81; Cl, 8.35; N, 3.30; O, 7.53

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 550.00	2 Weeks
50mg	USD 1,530.00	2 Weeks

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Synonym

SKF-83822 hydrobromide, SKF-83822 HBr

IUPAC/Chemical Name

6-Chloro-2,3,4,5-tetrahydro-1-(3-methylphenyl)-3-(2-propenyl)-1H-3-benzazepine-7,8-diol hydrobromide

InChi Key

CFWPKYBBXBANLU-UHFFFAOYSA-N

InChi Code

InChI=1S/C20H22ClNO2.BrH/c1-3-8-22-9-7-15-16(11-18(23)20(24)19(15)21)17(12-22)14-6-4-5-13(2)10-14;/h3-6,10-11,17,23-24H,1,7-9,12H2,2H3;1H

SMILES Code

OC1=C(O)C=C2C(C3=CC=CC(C)=C3)CN(CC=C)CCC2=C1Cl.[H]Br

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO and ethanol

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

For SKF-83822 HBr, Ki values are 3.2, 3.1, 186, 66, 335, 1167, 1251 and 1385 nM at recombinant D1, D5, D2, D3, D4, 5-HT2A, α1A and α1B receptors respectively. SKF-83822 HBr stimulates adenylyl cyclase (EC50 = 65 nM) but not phosphoinositide hydrolysis.

In vitro activity:

Although SKF-83822 does not directly activate the D1-D2 receptor heteromer, it still causes a desensitization of the calcium signal. This implies that when SKF-83822 occupies the D1 receptor binding pocket, it triggers conformational changes that lead to desensitization without activating the heteromer. An increase in GRK2 expression decreases the calcium signal, regardless of prior exposure to SKF-83959 or SKF-83822. Reference: J Biol Chem. 2010 Nov 5;285(45):35092-103. https://pubmed.ncbi.nlm.nih.gov/20807772/

In vivo activity:

This study investigated the complex relationship between dopamine D(1)-like receptor activation and orofacial behavior. In freely moving rats, SKF-83959 induced more jaw movements per episode of syntactic grooming than SKF-83822, while SKF-83822 induced more jaw movements during non-syntactic grooming than SKF-83959. SKF-83822 stimulated dopamine D(1)-like receptors and activated adenylate cyclase, while SKF-83959 stimulates dopamine D(1)-like receptors and activates phosphoinositide hydrolysis. Reference: Eur J Pharmacol. 2010 Apr 25;632(1-3):39-44. https://pubmed.ncbi.nlm.nih.gov/20122923/

	Solvent	mg/mL	mM
Solubility
	DMSO	34.4	100.00
	Ethanol	3.4	10.00

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 424.76 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Ehrlich AT, Furuyashiki T, Kitaoka S, Kakizuka A, Narumiya S. Prostaglandin E receptor EP1 forms a complex with dopamine D1 receptor and directs D1-induced cAMP production to adenylyl cyclase 7 through mobilizing G(βγ) subunits in human embryonic kidney 293T cells. Mol Pharmacol. 2013 Sep;84(3):476-86. doi: 10.1124/mol.113.087288. Epub 2013 Jul 10. PMID: 23842570. 2. Verma V, Hasbi A, O'Dowd BF, George SR. Dopamine D1-D2 receptor Heteromer-mediated calcium release is desensitized by D1 receptor occupancy with or without signal activation: dual functional regulation by G protein-coupled receptor kinase 2. J Biol Chem. 2010 Nov 5;285(45):35092-103. doi: 10.1074/jbc.M109.088625. Epub 2010 Aug 31. PMID: 20807772; PMCID: PMC2966123. 3. Kim JE, Lee DS, Kim TH, Park H, Kim MJ, Kang TC. PLPP/CIN inhibits dopamine D1 receptor-mediated seizure activity via DARPP-32 serine 97 dephosphorylation in the mouse hippocampus. Neuropharmacology. 2023 May 1;228:109462. doi: 10.1016/j.neuropharm.2023.109462. Epub 2023 Feb 14. PMID: 36792029. 4. Fujita S, Kiguchi M, Kobayashi M, Kinsella A, Koshikawa N, Waddington JL. Assessment of jaw movements by magnetic sensor in relation to topographies of orofacial behaviour in freely moving rats: Studies with the dopamine D(1)-like receptor agonists SKF 83822 vs SKF 83959. Eur J Pharmacol. 2010 Apr 25;632(1-3):39-44. doi: 10.1016/j.ejphar.2010.01.018. Epub 2010 Feb 1. PMID: 20122923.

In vitro protocol:

In vivo protocol:

1. Kim JE, Lee DS, Kim TH, Park H, Kim MJ, Kang TC. PLPP/CIN inhibits dopamine D1 receptor-mediated seizure activity via DARPP-32 serine 97 dephosphorylation in the mouse hippocampus. Neuropharmacology. 2023 May 1;228:109462. doi: 10.1016/j.neuropharm.2023.109462. Epub 2023 Feb 14. PMID: 36792029. 2. Fujita S, Kiguchi M, Kobayashi M, Kinsella A, Koshikawa N, Waddington JL. Assessment of jaw movements by magnetic sensor in relation to topographies of orofacial behaviour in freely moving rats: Studies with the dopamine D(1)-like receptor agonists SKF 83822 vs SKF 83959. Eur J Pharmacol. 2010 Apr 25;632(1-3):39-44. doi: 10.1016/j.ejphar.2010.01.018. Epub 2010 Feb 1. PMID: 20122923.

1. Undie et al (1994) Evidence for a distinct D1-like DA receptor that couples to activation of phosphoinositide metabolism in brain. J.Neurochem. 62 2045 PMID: 7908949 2. Peacock and Gerlach (2001) Aberrant behavioural effects of a DA D1 receptor antagonist and agonist in monkeys: evidence of uncharted DA D1 receptor actions. Biol.Psychiatry 50 501 PMID: 11600103 3. O'Sullivan et al (2004) SK&F 83822 distinguishes adenylyl cyclase from phospholipase C-coupled D1-like receptors: behavioural topography. Eur.J.Pharmacol. 486 273 PMID: 14985049

Description:

Chemical Structure

Theoretical Analysis

Price and Availability

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