(-)-(1R,3S)-3-ADAMANTYL-1-(AMINOMETHYL)-3,4-DIHYDRO-5,6-DIHYDROXY-1H-2-BENZOPYRAN HYDROCHLORIDE
- Product Name
- (-)-(1R,3S)-3-ADAMANTYL-1-(AMINOMETHYL)-3,4-DIHYDRO-5,6-DIHYDROXY-1H-2-BENZOPYRAN HYDROCHLORIDE
- CAS No.
- 145307-34-2
- Chemical Name
- (-)-(1R,3S)-3-ADAMANTYL-1-(AMINOMETHYL)-3,4-DIHYDRO-5,6-DIHYDROXY-1H-2-BENZOPYRAN HYDROCHLORIDE
- Synonyms
- A 77636;A 77636 HYDROCHLORIDE;A-77636 hydrochloride hydrate;A-77636 hydrate hydrochloride;(1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol hydrochloride;(-)-(1R,3S)-3-ADAMANTYL-1-(AMINOMETHYL)-3,4-DIHYDRO-5,6-DIHYDROXY-1H-2-BENZOPYRAN HYDROCHLORIDE;(-)-(1R,3S)-3-ADAMANTYL-1-(AMINOMETHYL)-3,4-DIHYDRO-5,6-DIHYDROXY-1H-2-BENZOPYRAN HYDROCHLORIDE;(?)-(1R,3S)-3-Adamantyl-1-(aminomethyl)-3,4-dihydro-5,6-dihydroxy-1H-2-benzopyran hydrochloride hydrate;(-)-(1R,3S)-3-Adamantyl-1-(aminomethyl)-3,4-dihydro-5,6-dihydroxy-1H-2-benzopyran hydrate hydrochloride;(1R)-cis-1-Aminomethyl-3,4-dihydro-3-tricyclo[3.3.1.13.7]dec-1-yl-[1-h]-2-benzopyran-5,6-diolhydrochloride
- CBNumber
- CB1208041
- Molecular Formula
- C20H28ClNO3
- Formula Weight
- 365.89
- MOL File
- 145307-34-2.mol
(-)-(1R,3S)-3-ADAMANTYL-1-(AMINOMETHYL)-3,4-DIHYDRO-5,6-DIHYDROXY-1H-2-BENZOPYRAN HYDROCHLORIDE Property
- storage temp.
- −20°C
- solubility
- H2O: 10 mg/mL
- form
- solid
- color
- off-white
- Water Solubility
- Soluble to 100 mM in water
Safety
- WGK Germany
- 3
N-Bromosuccinimide Price
- Product number
- A255
- Product name
- A-77636 hydrochloride hydrate
- Purity
- ≥98% (HPLC), solid
- Packaging
- 10mg
- Price
- $390
- Updated
- 2024/03/01
- Product number
- 24316
- Product name
- A-77636 (hydrochloride)
- Purity
- ≥98%
- Packaging
- 1mg
- Price
- $44
- Updated
- 2024/03/01
- Product number
- 24316
- Product name
- A-77636 (hydrochloride)
- Purity
- ≥98%
- Packaging
- 5mg
- Price
- $161
- Updated
- 2024/03/01
- Product number
- 24316
- Product name
- A-77636 (hydrochloride)
- Purity
- ≥98%
- Packaging
- 10mg
- Price
- $235
- Updated
- 2024/03/01
- Product number
- 1701
- Product name
- A77636hydrochloride
- Purity
- ≥98%(HPLC)
- Packaging
- 10
- Price
- $216
- Updated
- 2021/12/16
(-)-(1R,3S)-3-ADAMANTYL-1-(AMINOMETHYL)-3,4-DIHYDRO-5,6-DIHYDROXY-1H-2-BENZOPYRAN HYDROCHLORIDE Chemical Properties,Usage,Production
Description
A-77636 is a dopamine D1 receptor agonist (Ki = 40 nM). It induces activity equal to or greater than dopamine in an adenylate cyclase assay of D1 receptor activity in fish retina and rat caudate putamen (EC50s = 7.4 and 1.1 nM, respectively) but does not show agonist activity at D2 receptors expressed in MMQ cells when used at concentrations up to 10 μM. A-77636 (10 μM) induces desensitization of dopamine-stimulated cAMP accumulation and downregulation of D1 receptors, reducing D1 receptor expression by 79% in C-6 glioma cells expressing monkey D1A receptors. In a marmoset model of Parkinson''s disease induced by MPTP, A-77636 (3 μmol/kg, s.c.) increases locomotor activity 5.3-fold and reduces disease severity. Subcutaneous administration of A-77636 elicits cortical acetylcholine release at a dose of 1 μmol/kg. It also elicits over a 230% increase in cortical and hippocampal acetylcholine release when administered at a dose of 4 μmol/kg, an effect that is blocked by the D1 antagonist SCH 23390 .
Uses
The dopamine receptors play important role in cognition, memory, learning, and motor control (1). These receptors have been implicated as a therapeutic target for many psychiatric and neurological disorders. A 77636 Hydrochloride is a selective dopamine D1-like receptor agonist with antiparkinsonian properties (2,3).
Definition
ChEBI: (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol hydrochloride is a hydrochloride salt obtained by mixing equimolar amounts of (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol with hydrochloric acid. Potent and selective dopamine D1-like receptor agonist (pEC50 values are 8.97 and < 5 for D1-like and D2-like receptors respectively). Displays anti-Parkinsonian activity following oral administration in vivo. It has a role as an antiparkinson drug and a dopamine agonist. It contains a (1R,3S)-3-(adamantan-1-yl)-1-(ammoniomethyl)-3,4-dihydroisochromene-5,6-diol(1+).
Biological Activity
Potent and selective dopamine D 1 -like receptor agonist (pEC 50 values are 8.97 and < 5 for D 1 -like and D 2 -like receptors respectively). Displays anti-Parkinsonian activity following oral administration in vivo .
storage
Store at -20°C
References
[1]. kebabian jw, britton dr, deninno mp, et al. a-77636: a potent and selective dopamine d1 receptor agonist with antiparkinsonian activity in marmosets. eur j pharmacol, 1992, 229(2-3): 203-209.
[2]. lin cw, bianchi br, miller tr, et al. persistent activation of the dopamine d1 receptor contributes to prolonged receptor desensitization: studies with a-77636. j pharmacol exp ther, 1996, 276(3): 1022-1029.
[3]. acquas e, day jc, fibiger hc. the potent and selective dopamine d1 receptor agonist a-77636 increases cortical and hippocampal acetylcholine release in the rat. eur j pharmacol, 1994, 260(1): 85-87.
(-)-(1R,3S)-3-ADAMANTYL-1-(AMINOMETHYL)-3,4-DIHYDRO-5,6-DIHYDROXY-1H-2-BENZOPYRAN HYDROCHLORIDE Preparation Products And Raw materials
Raw materials
Preparation Products
(-)-(1R,3S)-3-ADAMANTYL-1-(AMINOMETHYL)-3,4-DIHYDRO-5,6-DIHYDROXY-1H-2-BENZOPYRAN HYDROCHLORIDE Suppliers
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