(-)-(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

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(-)-(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

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Safety

WGK Germany: 3

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: A255
Product name: A-77636 hydrochloride hydrate
Purity: ≥98% (HPLC), solid
Packaging: 10mg
Price: $390
Updated: 2024/03/01

Cayman Chemical

Product number: 24316
Product name: A-77636 (hydrochloride)
Purity: ≥98%
Packaging: 1mg
Price: $44
Updated: 2024/03/01

Cayman Chemical

Product number: 24316
Product name: A-77636 (hydrochloride)
Purity: ≥98%
Packaging: 5mg
Price: $161
Updated: 2024/03/01

Cayman Chemical

Product number: 24316
Product name: A-77636 (hydrochloride)
Purity: ≥98%
Packaging: 10mg
Price: $235
Updated: 2024/03/01

Tocris

Product number: 1701
Product name: A77636hydrochloride
Purity: ≥98%(HPLC)
Packaging: 10
Price: $216
Updated: 2021/12/16

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(-)-(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 (K_i = 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 D_1A 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

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(-)-(1R,3S)-3-ADAMANTYL-1-(AMINOMETHYL)-3,4-DIHYDRO-5,6-DIHYDROXY-1H-2-BENZOPYRAN HYDROCHLORIDE Suppliers

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145307-34-2, (-)-(1R,3S)-3-ADAMANTYL-1-(AMINOMETHYL)-3,4-DIHYDRO-5,6-DIHYDROXY-1H-2-BENZOPYRAN HYDROCHLORIDERelated Search:

L-NORADRENALINE HYDROCHLORIDE C-ISOCHROMAN-1-YL-METHYLAMINE (-)-(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-CIS)-1-(AMINOMETHYL)-3,4-DIHYDRO-3-TRICYCLO[3.3.1.13,7]DEC-1-YL-[1H]-2-BENZOPYRAN-5,6-DIOL HYDROCHLORIDE

A 77636 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

A 77636

(-)-(1R,3S)-3-Adamantyl-1-(aminomethyl)-3,4-dihydro-5,6-dihydroxy-1H-2-benzopyran hydrate hydrochloride

A-77636 hydrate hydrochloride

(?)-(1R,3S)-3-Adamantyl-1-(aminomethyl)-3,4-dihydro-5,6-dihydroxy-1H-2-benzopyran hydrochloride hydrate

A-77636 hydrochloride hydrate

(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

145307-34-2