CHEBI:64002 - N-allyl-6-chloro-1-(3-methylphenyl)-2,3,4,5-tetrahydro-3-benzazepine-7,8-diol hydrobromide

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ChEBI Name N-allyl-6-chloro-1-(3-methylphenyl)-2,3,4,5-tetrahydro-3-benzazepine-7,8-diol hydrobromide
ChEBI ID CHEBI:64002
ChEBI ASCII Name N-allyl-6-chloro-1-(3-methylphenyl)-2,3,4,5-tetrahydro-3-benzazepine-7,8-diol hydrobromide
Definition A hydrobromide salt prepared from N-allyl-6-chloro-1-(3-methylphenyl)-2,3,4,5-tetrahydro-3-benzazepine-7,8-diol and one equivalent of hydrogen bromide. High affinity, selective dopamine D1-like receptor agonist. Ki values are 3.2, 3.1, 186, 66, 335, 1167, 1251 and 1385 nM at recombinant D1, D5, D2, D3, D4, 5-HT2A, α1A and α1B receptors respectively. Stimulates adenylyl cyclase (EC50 = 65 nM) but not phosphoinositide hydrolysis. Induces extreme arousal and hyperlocomotion following subcutaneous administration in monkeys.
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Formula C20H23BrClNO2
Net Charge 0
Average Mass 424.75900
Monoisotopic Mass 423.06007
InChI InChI=1S/C20H22ClNO2.BrH/c1-3-8-22-9-7-15-16(11-18(23)20(24)19(15)21)17(12-22)14-6-4-5-13(2)10-14;/h3-6,10-11,17,23-24H,1,7-9,12H2,2H3;1H
InChIKey CFWPKYBBXBANLU-UHFFFAOYSA-N
SMILES Br.Cc1cccc(c1)C1CN(CCc2c1cc(O)c(O)c2Cl)CC=C
Roles Classification
Biological Role(s): dopamine agonist
A drug that binds to and activates dopamine receptors.
Application(s): dopamine agonist
A drug that binds to and activates dopamine receptors.
prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
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ChEBI Ontology
Outgoing N-allyl-6-chloro-1-(3-methylphenyl)-2,3,4,5-tetrahydro-3-benzazepine-7,8-diol hydrobromide (CHEBI:64002) has part N-allyl-6-chloro-1-(3-methylphenyl)-2,3,4,5-tetrahydro-3-benzazepinium-7,8-diol(1+) (CHEBI:64003)
N-allyl-6-chloro-1-(3-methylphenyl)-2,3,4,5-tetrahydro-3-benzazepine-7,8-diol hydrobromide (CHEBI:64002) has role dopamine agonist (CHEBI:51065)
N-allyl-6-chloro-1-(3-methylphenyl)-2,3,4,5-tetrahydro-3-benzazepine-7,8-diol hydrobromide (CHEBI:64002) has role prodrug (CHEBI:50266)
N-allyl-6-chloro-1-(3-methylphenyl)-2,3,4,5-tetrahydro-3-benzazepine-7,8-diol hydrobromide (CHEBI:64002) is a hydrobromide (CHEBI:48367)
IUPAC Name
6-chloro-1-(3-methylphenyl)-3-(prop-2-en-1-yl)-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-diol hydrobromide
Synonyms Sources
3-allyl-6-chloro-1-(3-methylphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-diol hydrobromide IUPAC
3-allyl-6-chloro-7,8-dihydroxy-1-(3-methylphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepinium bromide IUPAC
6-chloro-7,8-dihydroxy-1-(3-methylphenyl)-3-(prop-2-en-1-yl)-2,3,4,5-tetrahydro-1H-3-benzazepinium bromide IUPAC
SKF 83822 hydrobromide ChEBI
Registry Number Type Source
5198936 Reaxys Registry Number Reaxys
Last Modified
22 February 2012