Basic information
- CAS
778546-51-3- Standard SMILES
NC[C@@H]1O[C@H](C23CC4CC(CC(C4)C2)C3)Cc2c1ccc(O)c2O- InChIKey
QLJOSZATCBCBDR-DFKUFRTHSA-N- Molecular formula
- C20H27NO3
- Average molar mass
- 329.4 g/mol
- Monoisotopic mass
- 329.19909372
Overview
(1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol is an isochromene that is 3,4-dihydroisochromene-5,6-diol bearing additional aminomethyl and 1-adamantyl substituents at positions 1 and 3 respectively (the 1R,3S-diastereomer). 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 is a member of catechols, a member of isochromenes, a primary amino compound and a member of adamantanes. It is a conjugate base of a (1R,3S)-3-(adamantan-1-yl)-1-(ammoniomethyl)-3,4-dihydroisochromene-5,6-diol(1+).
Names & identifiers
- Preferred name
- (1R,3S)-1-(Aminomethyl)-3,4-dihydro-3-tricyclo(3.3.1.13,7)dec-1-yl-1H-2-benzopyran-5,6-diol
- IUPAC
- (1R,3S)-3-(1-adamantyl)-1-(aminomethyl)-3,4-dihydro-1H-isochromene-5,6-diol
- English name
- 1H-2-Benzopyran-5,6-diol, 1-(aminomethyl)-3,4-dihydro-3-tricyclo[3.3.1.13,7]dec-1-yl-, (1R,3S)-
- Molecular formula
- C20H27NO3
- Molecular weight
- 329.43
Names & synonyms
A-77636778546-51-38PDA66H6ZI1H-2-Benzopyran-5,6-diol, 1-(aminomethyl)-3,4-dihydro-3-tricyclo(3.3.1.13,7)dec-1-yl-, (1R,3S)-1H-2-Benzopyran-5,6-diol, 1-(aminomethyl)-3,4-dihydro-3-tricyclo(3.3.1.13,7)dec-1-yl-, (1R-cis)RefChem:1049458(1R,3S)-1-(Aminomethyl)-3,4-dihydro-3-tricyclo(3.3.1.13,7)dec-1-yl-1H-2-benzopyran-5,6-diolA 77636UNII-8PDA66H6ZI(1R,3S)-3-(1-adamantyl)-1-(aminomethyl)-3,4-dihydro-1H-isochromene-5,6-diolCHEMBL291143A77636
Show more names
1H-2-Benzopyran-5,6-diol, 1-(aminomethyl)-3,4-dihydro-3-tricyclo[3.3.1.13,7]dec-1-yl-, (1R,3S)-
MLS001056780(1R,3S)-3-(Adamantan-1-yl)-1-(aminomethyl)isochromane-5,6-diol(1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol(1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydro-1H-isochromene-5,6-diol145307-34-2SMR000326988NCGC00015025-01Tocris-1701
Properties
Computed structural properties
- XLogP
- 3
- Topological polar surface area
- 75.7 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 454
Physicochemical properties
- Boiling point
- 515.3 · 515.3±50.0 °C(Predicted)
- Density
- 1.283 · 1.283±0.06 g/cm3(Predicted)
- pka
- 9.55 · 9.55±0.60(Predicted)
- FDA UNII
- 8 PDA66H6ZI · 8PDA66H6ZI
Chemistry & industry
Applications
UsesA-77636 is an orally active, potent, selective and long-acting dopamine D1 receptor agonist (pEC50 = 8.13; EC50 = 1.1 nM). A-77636 shows the highest affinity (pKi = 7.40 ± 0.09; Ki = 39.8 nM) for the dopamine D1 receptor. A-77636 shows antiparkinsonian activity[1].
Suppliers2 total
上海陶术生物科技股份有限公司13564774135 · [email protected]
TargetMol中国（陶术生物）15002134094 · [email protected]
Additional notes
DefinitionChEBI: (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol is an isochromene that is 3,4-dihydroisochromene-5,6-diol bearing additional aminomethyl and 1-adamantyl substituents at positions 1 and 3 respectively (the 1R,3S-diastereomer). Potent and selective dopamine D1-like receptor agonist (pEC50 values are 8.97 and
Related reactions
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Compound notes
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