A 77636 hydrochloride

Base Information

• Chemical Name: A 77636 hydrochloride
• CAS No.: 145307-34-2
• Molecular Formula: C₂₀H₂₇NO₃*ClH
• Molecular Weight: 365.9
• UNII: WA6RGP1J4W
• DSSTox Substance ID: DTXSID1042576
• Wikidata: Q27133013
• Metabolomics Workbench ID: 63128
• ChEMBL ID: CHEMBL1256876
• Mol file: 145307-34-2.mol

Synonyms:3-(1'-adamantyl)-1-aminomethyl-3,4-dihydro-5,6-dihydroxy-1H-2-benzopyran hydrochloride;A 77636;A-77636;A77636

Chemical Property of A 77636 hydrochloride

Chemical Property:

• Vapor Pressure: 3.06E-11mmHg at 25°C
• Boiling Point: 515.3°C at 760 mmHg
• Flash Point: 265.5°C
• PSA: 75.71000
• LogP: 4.75760
• Storage Temp.: −20°C
• Solubility.: H2O: 10 mg/mL
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 365.1757714
• Heavy Atom Count: 25
• Complexity: 454

Purity/Quality:

97% ^*data from raw suppliers

A 77636 hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C2CC3CC1CC(C2)(C3)C4CC5=C(C=CC(=C5O)O)C(O4)CN.Cl
• Isomeric SMILES: C1[C@H](O[C@H](C2=C1C(=C(C=C2)O)O)CN)C34CC5CC(C3)CC(C5)C4.Cl
• 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).

Technology Process of A 77636 hydrochloride

There total 6 articles about A 77636 hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

(1R,3S)-3-(1'-adamantyl)-1-(aminomethyl)-5,6-(cyclohexylidenedioxy)-3,4-dihydro-1H-2-benzopyran (145238-47-7) → (1R,3S)-3-adamantyl-1-(aminomethyl)-3,4-dihydro-5,6-dihydroxy-1H-2-benzopyran hydrochloride (145307-34-2)

Guidance literature:

With hydrogenchloride; In 1,2-dimethoxyethane; water; for 3h; Heating;

DOI:10.1021/jo00052a025

Reference yield:

C24H30O3 (145238-40-0) → (1R,3S)-3-adamantyl-1-(aminomethyl)-3,4-dihydro-5,6-dihydroxy-1H-2-benzopyran hydrochloride (145307-34-2)

Guidance literature:

Multi-step reaction with 4 steps

1: BH₃*THF / proline-derived oxazaborolidine / tetrahydrofuran / Ambient temperature

2: 85 percent / trimethylsilyl triflate / acetonitrile / 2 h / Heating

3: 79 g / 15percent aq. NaOH / methanol; tetrahydrofuran / 3 h / 50 °C

4: 80 percent / 5N HCl / 1,2-dimethoxy-ethane; H₂O / 3 h / Heating

With hydrogenchloride; sodium hydroxide; borane-THF; trimethylsilyl trifluoromethanesulfonate; proline-derived oxazaborolidine; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; water; acetonitrile;

DOI:10.1021/jo00052a025

Reference yield:

(R)-(1'-adamantyl)ethylene oxide (145238-42-2) → (1R,3S)-3-adamantyl-1-(aminomethyl)-3,4-dihydro-5,6-dihydroxy-1H-2-benzopyran hydrochloride (145307-34-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) n-BuLi, 2.) BF₃*OEt₂ / 1.) hexane, THF, a) 0 deg C to r.t., 0.5 h, b) r.t., 3.5 h, 2.) THF, -78 deg C, 30 min

2: 85 percent / trimethylsilyl triflate / acetonitrile / 2 h / Heating

3: 79 g / 15percent aq. NaOH / methanol; tetrahydrofuran / 3 h / 50 °C

4: 80 percent / 5N HCl / 1,2-dimethoxy-ethane; H₂O / 3 h / Heating

With hydrogenchloride; sodium hydroxide; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; water; acetonitrile;

DOI:10.1021/jo00052a025

upstream raw materials:

(1R,3S)-3-(1'-adamantyl)-1-(aminomethyl)-5,6-(cyclohexylidenedioxy)-3,4-dihydro-1H-2-benzopyran

C₂₄H₃₀O₃

(R)-(1'-adamantyl)ethylene oxide

(1R)-1-(1'-adamantyl)-2-bromo-1-hydroxyethane