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(1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol
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.

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05. Industrial Uses: pharmaceutical [CHEBI:52217] > drug [CHEBI:23888] > antidyskinesia agent [CHEBI:66956] > antiparkinson drug [CHEBI:48407] > (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol [CHEBI:64080]
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03. Biological Effects of Specific Chemicals 
03. Biological Effects of Specific Chemicals
 pharmacological uses [CHEBI:52210] (736) 
 neurotransmitter agent [CHEBI:35942] (471) 
 dopaminergic agent [CHEBI:48560] (99) 
 dopamine agonist [CHEBI:51065] (26) 
 (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol [CHEBI:64080] (1)
05. Industrial Uses 
05. Industrial Uses
 pharmaceutical [CHEBI:52217] (1978) 
 drug [CHEBI:23888] (1930) 
 antidyskinesia agent [CHEBI:66956] (43) 
 antiparkinson drug [CHEBI:48407] (41) 
 (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol [CHEBI:64080] (1)
08. Chemical Category 
08. Chemical Category
 main group molecular entity [CHEBI:33579] (25650) 
 s-block molecular entity [CHEBI:33674] (7287) 
 hydrogen molecular entity [CHEBI:33608] (6932) 
 hydroxides [CHEBI:24651] (5641) 
 organic hydroxy compound [CHEBI:33822] (3050) 
 phenols [CHEBI:33853] (868) 
 benzenediols [CHEBI:33570] (188) 
 catechols [CHEBI:33566] (97) 
 (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol [CHEBI:64080] (1)
 p-block molecular entity [CHEBI:33675] (25343) 
 pnictogen molecular entity [CHEBI:33302] (10027) 
 nitrogen molecular entity [CHEBI:51143] (7930) 
 organonitrogen compound [CHEBI:35352] (6705) 
 organic amino compound [CHEBI:50047] (2472) 
 primary amino compound [CHEBI:50994] (104) 
 (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol [CHEBI:64080] (1)
 chalcogen molecular entity [CHEBI:33304] (15225) 
 oxygen molecular entity [CHEBI:25806] (14414) 
 hydroxides [CHEBI:24651] (5641) 
 organic hydroxy compound [CHEBI:33822] (3050) 
 phenols [CHEBI:33853] (868) 
 benzenediols [CHEBI:33570] (188) 
 catechols [CHEBI:33566] (97) 
 (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol [CHEBI:64080] (1)
 organooxygen compound [CHEBI:36963] (11352) 
 oxacycle [CHEBI:38104] (2002) 
 benzopyran [CHEBI:22727] (349) 
 2-benzopyran [CHEBI:38444] (21) 
 isochromenes [CHEBI:38761] (11) 
 (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol [CHEBI:64080] (1)
 organochalcogen compound [CHEBI:36962] (11874) 
 organooxygen compound [CHEBI:36963] (11352) 
 oxacycle [CHEBI:38104] (2002) 
 benzopyran [CHEBI:22727] (349) 
 2-benzopyran [CHEBI:38444] (21) 
 isochromenes [CHEBI:38761] (11) 
 (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol [CHEBI:64080] (1)
 carbon group molecular entity [CHEBI:33582] (23847) 
 organic molecular entity [CHEBI:50860] (23769) 
 heteroorganic entity [CHEBI:33285] (15197) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 oxacycle [CHEBI:38104] (2002) 
 benzopyran [CHEBI:22727] (349) 
 2-benzopyran [CHEBI:38444] (21) 
 isochromenes [CHEBI:38761] (11) 
 (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol [CHEBI:64080] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 benzopyran [CHEBI:22727] (349) 
 2-benzopyran [CHEBI:38444] (21) 
 isochromenes [CHEBI:38761] (11) 
 (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol [CHEBI:64080] (1)
 organonitrogen compound [CHEBI:35352] (6705) 
 organic amino compound [CHEBI:50047] (2472) 
 primary amino compound [CHEBI:50994] (104) 
 (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol [CHEBI:64080] (1)
 organochalcogen compound [CHEBI:36962] (11874) 
 organooxygen compound [CHEBI:36963] (11352) 
 oxacycle [CHEBI:38104] (2002) 
 benzopyran [CHEBI:22727] (349) 
 2-benzopyran [CHEBI:38444] (21) 
 isochromenes [CHEBI:38761] (11) 
 (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol [CHEBI:64080] (1)
 organic hydroxy compound [CHEBI:33822] (3050) 
 phenols [CHEBI:33853] (868) 
 benzenediols [CHEBI:33570] (188) 
 catechols [CHEBI:33566] (97) 
 (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol [CHEBI:64080] (1)
 organic amino compound [CHEBI:50047] (2472) 
 primary amino compound [CHEBI:50994] (104) 
 (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol [CHEBI:64080] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 oxacycle [CHEBI:38104] (2002) 
 benzopyran [CHEBI:22727] (349) 
 2-benzopyran [CHEBI:38444] (21) 
 isochromenes [CHEBI:38761] (11) 
 (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol [CHEBI:64080] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 benzopyran [CHEBI:22727] (349) 
 2-benzopyran [CHEBI:38444] (21) 
 isochromenes [CHEBI:38761] (11) 
 (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol [CHEBI:64080] (1)
 carbocyclic compound [CHEBI:33598] (1130) 
 carbopolycyclic compound [CHEBI:35294] (493) 
 adamantanes [CHEBI:51339] (10) 
 (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol [CHEBI:64080] (1)
 organic aromatic compound [CHEBI:33659] (3593) 
 phenols [CHEBI:33853] (868) 
 benzenediols [CHEBI:33570] (188) 
 catechols [CHEBI:33566] (97) 
 (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol [CHEBI:64080] (1)
 polyatomic entity [CHEBI:36357] (18777) 
 molecule [CHEBI:25367] (11520) 
 cyclic compound [CHEBI:33595] (7817) 
 homocyclic compound [CHEBI:33597] (1134) 
 carbocyclic compound [CHEBI:33598] (1130) 
 carbopolycyclic compound [CHEBI:35294] (493) 
 adamantanes [CHEBI:51339] (10) 
 (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol [CHEBI:64080] (1)
 homopolycyclic compound [CHEBI:35295] (493) 
 carbopolycyclic compound [CHEBI:35294] (493) 
 adamantanes [CHEBI:51339] (10) 
 (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol [CHEBI:64080] (1)
 polycyclic compound [CHEBI:33635] (4078) 
 heteropolycyclic compound [CHEBI:33671] (2613) 
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 benzopyran [CHEBI:22727] (349) 
 2-benzopyran [CHEBI:38444] (21) 
 isochromenes [CHEBI:38761] (11) 
 (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol [CHEBI:64080] (1)
 homopolycyclic compound [CHEBI:35295] (493) 
 carbopolycyclic compound [CHEBI:35294] (493) 
 adamantanes [CHEBI:51339] (10) 
 (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol [CHEBI:64080] (1)
 aromatic compound [CHEBI:33655] (3799) 
 organic aromatic compound [CHEBI:33659] (3593) 
 phenols [CHEBI:33853] (868) 
 benzenediols [CHEBI:33570] (188) 
 catechols [CHEBI:33566] (97) 
 (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol [CHEBI:64080] (1)
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 oxacycle [CHEBI:38104] (2002) 
 benzopyran [CHEBI:22727] (349) 
 2-benzopyran [CHEBI:38444] (21) 
 isochromenes [CHEBI:38761] (11) 
 (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol [CHEBI:64080] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 benzopyran [CHEBI:22727] (349) 
 2-benzopyran [CHEBI:38444] (21) 
 isochromenes [CHEBI:38761] (11) 
 (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol [CHEBI:64080] (1)
 carbocyclic compound [CHEBI:33598] (1130) 
 carbopolycyclic compound [CHEBI:35294] (493) 
 adamantanes [CHEBI:51339] (10) 
 (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol [CHEBI:64080] (1)
 organic aromatic compound [CHEBI:33659] (3593) 
 phenols [CHEBI:33853] (868) 
 benzenediols [CHEBI:33570] (188) 
 catechols [CHEBI:33566] (97) 
 (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol [CHEBI:64080] (1)
 heterocyclic compound [CHEBI:5686] (5275) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 oxacycle [CHEBI:38104] (2002) 
 benzopyran [CHEBI:22727] (349) 
 2-benzopyran [CHEBI:38444] (21) 
 isochromenes [CHEBI:38761] (11) 
 (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol [CHEBI:64080] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 benzopyran [CHEBI:22727] (349) 
 2-benzopyran [CHEBI:38444] (21) 
 isochromenes [CHEBI:38761] (11) 
 (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol [CHEBI:64080] (1)
 heteropolycyclic compound [CHEBI:33671] (2613) 
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 benzopyran [CHEBI:22727] (349) 
 2-benzopyran [CHEBI:38444] (21) 
 isochromenes [CHEBI:38761] (11) 
 (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol [CHEBI:64080] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 oxacycle [CHEBI:38104] (2002) 
 benzopyran [CHEBI:22727] (349) 
 2-benzopyran [CHEBI:38444] (21) 
 isochromenes [CHEBI:38761] (11) 
 (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol [CHEBI:64080] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 benzopyran [CHEBI:22727] (349) 
 2-benzopyran [CHEBI:38444] (21) 
 isochromenes [CHEBI:38761] (11) 
 (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol [CHEBI:64080] (1)
 carbocyclic compound [CHEBI:33598] (1130) 
 carbopolycyclic compound [CHEBI:35294] (493) 
 adamantanes [CHEBI:51339] (10) 
 (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol [CHEBI:64080] (1)
 organic aromatic compound [CHEBI:33659] (3593) 
 phenols [CHEBI:33853] (868) 
 benzenediols [CHEBI:33570] (188) 
 catechols [CHEBI:33566] (97) 
 (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol [CHEBI:64080] (1)
 heteroatomic molecular entity [CHEBI:37577] (13672) 
 hydroxides [CHEBI:24651] (5641) 
 organic hydroxy compound [CHEBI:33822] (3050) 
 phenols [CHEBI:33853] (868) 
 benzenediols [CHEBI:33570] (188) 
 catechols [CHEBI:33566] (97) 
 (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol [CHEBI:64080] (1)
ChEBI Compound Accession Identifier:   [CHEBI:64080]
ChEBI Compound Description:   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.
ChEBI Compound Identification Number:   64080
ChEBI InChI Value:   InChI=1S/C20H27NO3/c21-10-17-14-1-2-16(22)19(23)15(14)6-18(24-17)20-7-11-3-12(8-20)5-13(4-11)9-20/h1-2,11-13,17-18,22-23H,3-10,21H2/t11?,12?,13?,17-,18-,20?/m0/s1
ChEBI InChIKey Value:   QLJOSZATCBCBDR-DFKUFRTHSA-N
ChEBI Compound Name:   (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol
ChEBI SMILES Value:   NC[C@@H]1O[C@@H](Cc2c(O)c(O)ccc12)C12CC3CC(CC(C3)C1)C2
ChEBI Substance ID:   135610884
ChEBI URL:   ChEBI:64080
ChemSpider ID:   NS
Ontomatica Chemical Accession Key (OnChAKey):   QLJOSZATCBCBDR_DFKUFRTHSA_N_000_000000
PubChem Compound ID:   6603703