Page last updated: 2024-12-07

7,8-dichloro-1,2,3,4-tetrahydroisoquinoline

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth

Description

7,8-dichloro-1,2,3,4-tetrahydroisoquinoline: potent reversible inhibitor of phenylethanolamine N-methyltransferase; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

7,8-dichloro-1,2,3,4-tetrahydroisoquinoline : A 1,2,3,4-tetrahydroisoquinoline hacing chloro substituents at the 7- and 8-positions. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID123920
CHEMBL ID287837
CHEBI ID160129
SCHEMBL ID1772370
MeSH IDM0059021

Synonyms (31)

Synonym
7,8-dichloro-1,2,3,4-tetrahydroisoquinoline
SKA ,
sk&f 64139
bdbm13014
chembl287837 ,
1YZ3 ,
7,8-dichloro-1,2,3,4-tetrahydro-isoquinoline; hydrochloride
skf 64139
CHEBI:160129 ,
61563-24-4
sk&f-64139
sk-64139
DB08550
isoquinoline, 7,8-dichloro-1,2,3,4-tetrahydro-
a0ep5o913j ,
unii-a0ep5o913j
AKOS013709661
SCHEMBL1772370
7,8-dichlorotetrahydroisoquinoline
7,8-dichloro-1,2,3,4-tetrahydro-isoquinoline
WFPUBEDBBOGGIQ-UHFFFAOYSA-N
dichloro-1,2,3,4-tetrahydroisoquinoline, 7,8-
skf-64139 free base
DTXSID90210570
FT-0768100
Q27097750
7,8-ichloro-1,2,3,4-etrahydroisoquinolie
CS-0064799
HY-113969
EN300-298884
Z1224524509

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
"After 7 day dosing with SK & F 64139, an inhibitor of adrenal and CNS PNMT, a stoichiometric relationship is observed between epinephrine decrease and norepinephrine increase in adrenal tissue."( Comparison of the effects of SK & F 29661 and 64139 upon adrenal and cardiac catecholamines.
Gessner, G; Pendleton, RG; Sawyer, J, 1980
)
0.26
" The dose-response curve for the LC inhibitory effect of the alpha 2-receptor agonist clonidine was shifted in parallel to the right by pretreatment with SK&F 64139."( Effect of adrenaline synthesis inhibition on brain noradrenaline neurons in locus coeruleus.
Elam, M; Engberg, G; Svensson, TH, 1981
)
0.26
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
isoquinolinesA class of organic heteropolycyclic compound consisting of isoquinoline and its substitution derivatives.
organochlorine compoundAn organochlorine compound is a compound containing at least one carbon-chlorine bond.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (10)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Phenylethanolamine N-methyltransferaseHomo sapiens (human)Ki0.00160.00160.00160.0016AID977610
Alpha-2A adrenergic receptorHomo sapiens (human)Ki3.27050.00010.807410.0000AID239340; AID257556
Phenylethanolamine N-methyltransferaseBos taurus (cattle)Ki445,253,633,489.63480.00312.329310.0000AID155137; AID155138; AID155145; AID155146; AID155167; AID155306; AID155308; AID156051; AID156064; AID1797148; AID313558
Phenylethanolamine N-methyltransferaseHomo sapiens (human)IC50 (µMol)2.50570.00302.505710.0000AID155319; AID155323; AID155324; AID405520
Phenylethanolamine N-methyltransferaseHomo sapiens (human)Ki0.19610.00161.35296.9000AID155320; AID155333; AID1796978; AID239072; AID239080; AID239624; AID257555; AID271160; AID282848; AID282849; AID282850; AID282851; AID282852; AID293029
Alpha-2B adrenergic receptorHomo sapiens (human)Ki0.02100.00020.725710.0000AID257556
Alpha-2C adrenergic receptorHomo sapiens (human)Ki0.02100.00030.483410.0000AID257556
Alpha-2B adrenergic receptorRattus norvegicus (Norway rat)Ki3,047,253,291,827.22070.00000.929610.0000AID239041; AID239195; AID271161; AID293030; AID35193; AID35195; AID35395; AID36945; AID37094; AID37366
Alpha-2C adrenergic receptorRattus norvegicus (Norway rat)Ki3,047,253,291,827.22070.00000.970810.0000AID239041; AID239195; AID271161; AID293030; AID35193; AID35195; AID35395; AID36945; AID37094; AID37366
Alpha-2A adrenergic receptorRattus norvegicus (Norway rat)Ki2,688,752,904,553.43360.00000.937510.0000AID1797149; AID219806; AID239041; AID239195; AID271161; AID293030; AID35193; AID35195; AID35395; AID36945; AID37094; AID37366
Purine nucleoside phosphorylase Bos taurus (cattle)Ki0.22000.00000.53072.7000AID156051
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (54)

Processvia Protein(s)Taxonomy
positive regulation of cytokine productionAlpha-2A adrenergic receptorHomo sapiens (human)
DNA replicationAlpha-2A adrenergic receptorHomo sapiens (human)
G protein-coupled receptor signaling pathwayAlpha-2A adrenergic receptorHomo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayAlpha-2A adrenergic receptorHomo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathwayAlpha-2A adrenergic receptorHomo sapiens (human)
Ras protein signal transductionAlpha-2A adrenergic receptorHomo sapiens (human)
Rho protein signal transductionAlpha-2A adrenergic receptorHomo sapiens (human)
female pregnancyAlpha-2A adrenergic receptorHomo sapiens (human)
positive regulation of cell population proliferationAlpha-2A adrenergic receptorHomo sapiens (human)
negative regulation of norepinephrine secretionAlpha-2A adrenergic receptorHomo sapiens (human)
regulation of vasoconstrictionAlpha-2A adrenergic receptorHomo sapiens (human)
actin cytoskeleton organizationAlpha-2A adrenergic receptorHomo sapiens (human)
platelet activationAlpha-2A adrenergic receptorHomo sapiens (human)
positive regulation of cell migrationAlpha-2A adrenergic receptorHomo sapiens (human)
activation of protein kinase activityAlpha-2A adrenergic receptorHomo sapiens (human)
activation of protein kinase B activityAlpha-2A adrenergic receptorHomo sapiens (human)
negative regulation of epinephrine secretionAlpha-2A adrenergic receptorHomo sapiens (human)
cellular response to hormone stimulusAlpha-2A adrenergic receptorHomo sapiens (human)
receptor transactivationAlpha-2A adrenergic receptorHomo sapiens (human)
vasodilationAlpha-2A adrenergic receptorHomo sapiens (human)
glucose homeostasisAlpha-2A adrenergic receptorHomo sapiens (human)
fear responseAlpha-2A adrenergic receptorHomo sapiens (human)
positive regulation of potassium ion transportAlpha-2A adrenergic receptorHomo sapiens (human)
positive regulation of MAP kinase activityAlpha-2A adrenergic receptorHomo sapiens (human)
positive regulation of MAPK cascadeAlpha-2A adrenergic receptorHomo sapiens (human)
positive regulation of epidermal growth factor receptor signaling pathwayAlpha-2A adrenergic receptorHomo sapiens (human)
negative regulation of calcium ion-dependent exocytosisAlpha-2A adrenergic receptorHomo sapiens (human)
negative regulation of insulin secretionAlpha-2A adrenergic receptorHomo sapiens (human)
intestinal absorptionAlpha-2A adrenergic receptorHomo sapiens (human)
thermoceptionAlpha-2A adrenergic receptorHomo sapiens (human)
negative regulation of lipid catabolic processAlpha-2A adrenergic receptorHomo sapiens (human)
positive regulation of membrane protein ectodomain proteolysisAlpha-2A adrenergic receptorHomo sapiens (human)
negative regulation of calcium ion transportAlpha-2A adrenergic receptorHomo sapiens (human)
negative regulation of insulin secretion involved in cellular response to glucose stimulusAlpha-2A adrenergic receptorHomo sapiens (human)
negative regulation of uterine smooth muscle contractionAlpha-2A adrenergic receptorHomo sapiens (human)
adrenergic receptor signaling pathwayAlpha-2A adrenergic receptorHomo sapiens (human)
adenylate cyclase-activating adrenergic receptor signaling pathwayAlpha-2A adrenergic receptorHomo sapiens (human)
adenylate cyclase-inhibiting adrenergic receptor signaling pathwayAlpha-2A adrenergic receptorHomo sapiens (human)
phospholipase C-activating adrenergic receptor signaling pathwayAlpha-2A adrenergic receptorHomo sapiens (human)
positive regulation of wound healingAlpha-2A adrenergic receptorHomo sapiens (human)
presynaptic modulation of chemical synaptic transmissionAlpha-2A adrenergic receptorHomo sapiens (human)
negative regulation of calcium ion transmembrane transporter activityAlpha-2A adrenergic receptorHomo sapiens (human)
methylationPhenylethanolamine N-methyltransferaseBos taurus (cattle)
epinephrine biosynthetic processPhenylethanolamine N-methyltransferaseBos taurus (cattle)
methylationPhenylethanolamine N-methyltransferaseHomo sapiens (human)
epinephrine biosynthetic processPhenylethanolamine N-methyltransferaseHomo sapiens (human)
catecholamine biosynthetic processPhenylethanolamine N-methyltransferaseHomo sapiens (human)
MAPK cascadeAlpha-2B adrenergic receptorHomo sapiens (human)
angiogenesisAlpha-2B adrenergic receptorHomo sapiens (human)
regulation of vascular associated smooth muscle contractionAlpha-2B adrenergic receptorHomo sapiens (human)
G protein-coupled receptor signaling pathwayAlpha-2B adrenergic receptorHomo sapiens (human)
cell-cell signalingAlpha-2B adrenergic receptorHomo sapiens (human)
female pregnancyAlpha-2B adrenergic receptorHomo sapiens (human)
negative regulation of norepinephrine secretionAlpha-2B adrenergic receptorHomo sapiens (human)
platelet activationAlpha-2B adrenergic receptorHomo sapiens (human)
activation of protein kinase B activityAlpha-2B adrenergic receptorHomo sapiens (human)
negative regulation of epinephrine secretionAlpha-2B adrenergic receptorHomo sapiens (human)
receptor transactivationAlpha-2B adrenergic receptorHomo sapiens (human)
positive regulation of MAPK cascadeAlpha-2B adrenergic receptorHomo sapiens (human)
positive regulation of neuron differentiationAlpha-2B adrenergic receptorHomo sapiens (human)
positive regulation of blood pressureAlpha-2B adrenergic receptorHomo sapiens (human)
positive regulation of uterine smooth muscle contractionAlpha-2B adrenergic receptorHomo sapiens (human)
adrenergic receptor signaling pathwayAlpha-2B adrenergic receptorHomo sapiens (human)
adenylate cyclase-activating adrenergic receptor signaling pathwayAlpha-2B adrenergic receptorHomo sapiens (human)
regulation of smooth muscle contractionAlpha-2C adrenergic receptorHomo sapiens (human)
G protein-coupled receptor signaling pathwayAlpha-2C adrenergic receptorHomo sapiens (human)
cell-cell signalingAlpha-2C adrenergic receptorHomo sapiens (human)
negative regulation of norepinephrine secretionAlpha-2C adrenergic receptorHomo sapiens (human)
regulation of vasoconstrictionAlpha-2C adrenergic receptorHomo sapiens (human)
platelet activationAlpha-2C adrenergic receptorHomo sapiens (human)
activation of protein kinase B activityAlpha-2C adrenergic receptorHomo sapiens (human)
negative regulation of epinephrine secretionAlpha-2C adrenergic receptorHomo sapiens (human)
receptor transactivationAlpha-2C adrenergic receptorHomo sapiens (human)
positive regulation of MAPK cascadeAlpha-2C adrenergic receptorHomo sapiens (human)
positive regulation of neuron differentiationAlpha-2C adrenergic receptorHomo sapiens (human)
adrenergic receptor signaling pathwayAlpha-2C adrenergic receptorHomo sapiens (human)
adenylate cyclase-activating adrenergic receptor signaling pathwayAlpha-2C adrenergic receptorHomo sapiens (human)
negative regulation of insulin secretionAlpha-2C adrenergic receptorHomo sapiens (human)
purine ribonucleoside salvagePurine nucleoside phosphorylase Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (16)

Processvia Protein(s)Taxonomy
alpha2-adrenergic receptor activityAlpha-2A adrenergic receptorHomo sapiens (human)
protein bindingAlpha-2A adrenergic receptorHomo sapiens (human)
protein kinase bindingAlpha-2A adrenergic receptorHomo sapiens (human)
alpha-1B adrenergic receptor bindingAlpha-2A adrenergic receptorHomo sapiens (human)
alpha-2C adrenergic receptor bindingAlpha-2A adrenergic receptorHomo sapiens (human)
thioesterase bindingAlpha-2A adrenergic receptorHomo sapiens (human)
heterotrimeric G-protein bindingAlpha-2A adrenergic receptorHomo sapiens (human)
protein homodimerization activityAlpha-2A adrenergic receptorHomo sapiens (human)
protein heterodimerization activityAlpha-2A adrenergic receptorHomo sapiens (human)
epinephrine bindingAlpha-2A adrenergic receptorHomo sapiens (human)
norepinephrine bindingAlpha-2A adrenergic receptorHomo sapiens (human)
guanyl-nucleotide exchange factor activityAlpha-2A adrenergic receptorHomo sapiens (human)
phenylethanolamine N-methyltransferase activityPhenylethanolamine N-methyltransferaseBos taurus (cattle)
phenylethanolamine N-methyltransferase activityPhenylethanolamine N-methyltransferaseHomo sapiens (human)
protein bindingPhenylethanolamine N-methyltransferaseHomo sapiens (human)
alpha2-adrenergic receptor activityAlpha-2B adrenergic receptorHomo sapiens (human)
protein bindingAlpha-2B adrenergic receptorHomo sapiens (human)
epinephrine bindingAlpha-2B adrenergic receptorHomo sapiens (human)
alpha2-adrenergic receptor activityAlpha-2C adrenergic receptorHomo sapiens (human)
protein bindingAlpha-2C adrenergic receptorHomo sapiens (human)
alpha-2A adrenergic receptor bindingAlpha-2C adrenergic receptorHomo sapiens (human)
protein homodimerization activityAlpha-2C adrenergic receptorHomo sapiens (human)
protein heterodimerization activityAlpha-2C adrenergic receptorHomo sapiens (human)
epinephrine bindingAlpha-2C adrenergic receptorHomo sapiens (human)
guanyl-nucleotide exchange factor activityAlpha-2C adrenergic receptorHomo sapiens (human)
purine-nucleoside phosphorylase activityPurine nucleoside phosphorylase Bos taurus (cattle)
guanosine phosphorylase activityPurine nucleoside phosphorylase Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (15)

Processvia Protein(s)Taxonomy
cytoplasmAlpha-2A adrenergic receptorHomo sapiens (human)
plasma membraneAlpha-2A adrenergic receptorHomo sapiens (human)
basolateral plasma membraneAlpha-2A adrenergic receptorHomo sapiens (human)
neuronal cell bodyAlpha-2A adrenergic receptorHomo sapiens (human)
axon terminusAlpha-2A adrenergic receptorHomo sapiens (human)
presynaptic active zone membraneAlpha-2A adrenergic receptorHomo sapiens (human)
dopaminergic synapseAlpha-2A adrenergic receptorHomo sapiens (human)
postsynaptic density membraneAlpha-2A adrenergic receptorHomo sapiens (human)
glutamatergic synapseAlpha-2A adrenergic receptorHomo sapiens (human)
GABA-ergic synapseAlpha-2A adrenergic receptorHomo sapiens (human)
receptor complexAlpha-2A adrenergic receptorHomo sapiens (human)
plasma membraneAlpha-2A adrenergic receptorHomo sapiens (human)
cytosolPhenylethanolamine N-methyltransferaseHomo sapiens (human)
cytosolPhenylethanolamine N-methyltransferaseHomo sapiens (human)
cytosolAlpha-2B adrenergic receptorHomo sapiens (human)
plasma membraneAlpha-2B adrenergic receptorHomo sapiens (human)
cell surfaceAlpha-2B adrenergic receptorHomo sapiens (human)
intracellular membrane-bounded organelleAlpha-2B adrenergic receptorHomo sapiens (human)
plasma membraneAlpha-2B adrenergic receptorHomo sapiens (human)
cytoplasmAlpha-2C adrenergic receptorHomo sapiens (human)
endosomeAlpha-2C adrenergic receptorHomo sapiens (human)
plasma membraneAlpha-2C adrenergic receptorHomo sapiens (human)
plasma membraneAlpha-2C adrenergic receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (69)

Assay IDTitleYearJournalArticle
AID21842Calculated partition coefficient (clogP)1999Journal of medicinal chemistry, Sep-09, Volume: 42, Issue:18
Synthesis and biochemical evaluation of 3-fluoromethyl-1,2,3, 4-tetrahydroisoquinolines as selective inhibitors of phenylethanolamine N-methyltransferase versus the alpha(2)-adrenoceptor.
AID155137Affinity for bovine Phenylethanolamine N-Methyltransferase (PNMT)1999Journal of medicinal chemistry, Sep-09, Volume: 42, Issue:18
Synthesis and biochemical evaluation of 3-fluoromethyl-1,2,3, 4-tetrahydroisoquinolines as selective inhibitors of phenylethanolamine N-methyltransferase versus the alpha(2)-adrenoceptor.
AID35216Ratio for binding affinity towards alpha-2 adrenoceptor to PNMT1999Journal of medicinal chemistry, Sep-09, Volume: 42, Issue:18
Synthesis and biochemical evaluation of 3-fluoromethyl-1,2,3, 4-tetrahydroisoquinolines as selective inhibitors of phenylethanolamine N-methyltransferase versus the alpha(2)-adrenoceptor.
AID237342Calculated partition coefficient (clogP)2004Journal of medicinal chemistry, Aug-26, Volume: 47, Issue:18
Inhibitors of phenylethanolamine N-methyltransferase that are predicted to penetrate the blood-brain barrier: design, synthesis, and evaluation of 3-fluoromethyl-7-(N-substituted aminosulfonyl)-1,2,3,4-tetrahydroisoquinolines that possess low affinity tow
AID239041Inhibition of [3H]clonidine binding to rat Alpha2 adrenoceptor2004Journal of medicinal chemistry, Aug-26, Volume: 47, Issue:18
Inhibitors of phenylethanolamine N-methyltransferase that are predicted to penetrate the blood-brain barrier: design, synthesis, and evaluation of 3-fluoromethyl-7-(N-substituted aminosulfonyl)-1,2,3,4-tetrahydroisoquinolines that possess low affinity tow
AID155167In vitro inhibitory activity measured against bovine adrenal phenylethanolamine N-methyltransferase(PNMT)1988Journal of medicinal chemistry, Apr, Volume: 31, Issue:4
Synthesis and evaluation of 3-substituted analogues of 1,2,3,4-tetrahydroisoquinoline as inhibitors of phenylethanolamine N-methyltransferase.
AID239624Inhibition of [3H]methyl-AdoMet binding to human phenylethanolamine N-methyl-transferase expressed in Escherichia coli BL212004Journal of medicinal chemistry, Aug-26, Volume: 47, Issue:18
Inhibitors of phenylethanolamine N-methyltransferase that are predicted to penetrate the blood-brain barrier: design, synthesis, and evaluation of 3-fluoromethyl-7-(N-substituted aminosulfonyl)-1,2,3,4-tetrahydroisoquinolines that possess low affinity tow
AID35195In vitro inhibition of [3H]clonidine binding at the alpha-2 adrenergic receptor.1999Journal of medicinal chemistry, Oct-21, Volume: 42, Issue:21
Enantiospecific synthesis of 3-fluoromethyl-, 3-hydroxymethyl-, and 3-chloromethyl-1,2,3,4-tetrahydroisoquinolines as selective inhibitors of phenylethanolamine N-methyltransferase versus the alpha(2)-adrenoceptor.
AID156064Inhibitory activity against bovine adrenal phenylethanolamine N-methyl-transferase (PNMT)1999Bioorganic & medicinal chemistry letters, Feb-08, Volume: 9, Issue:3
Comparative molecular field analysis (CoMFA) models of phenylethanolamine N-methyltransferase (PNMT) and the alpha2-adrenoceptor: the development of new, highly selective inhibitors of PNMT.
AID257557Selectivity of Adrenergic alpha-2 receptor over human PNMT2005Bioorganic & medicinal chemistry letters, Dec-01, Volume: 15, Issue:23
Inhibitors of phenylethanolamine N-methyltransferase devoid of alpha2-adrenoceptor affinity.
AID35193The compound was tested in vitro for binding affinity against Alpha-2 adrenergic receptor using [3H]clonidine1999Journal of medicinal chemistry, Aug-26, Volume: 42, Issue:17
Synthesis and evaluation of 3-trifluoromethyl-7-substituted-1,2,3, 4-tetrahydroisoquinolines as selective inhibitors of phenylethanolamine N-methyltransferase versus the alpha(2)-adrenoceptor.
AID239340Binding affinity against human alpha 2A adrenergic receptor in CHO cells using [3H]RX-821002 as radioligand2005Bioorganic & medicinal chemistry letters, Feb-15, Volume: 15, Issue:4
Exploring the active site of phenylethanolamine N-methyltransferase with 3-hydroxyethyl- and 3-hydroxypropyl-7-substituted-1,2,3,4-tetrahydroisoquinolines.
AID313558Inhibition of bovine PNMT by radiochemical assay2008Bioorganic & medicinal chemistry, Jan-01, Volume: 16, Issue:1
Synthesis of 4,5,6,7-tetrahydrothieno[3,2-c]pyridines and comparison with their isosteric 1,2,3,4-tetrahydroisoquinolines as inhibitors of phenylethanolamine N-methyltransferase.
AID156051Ability to inhibit phenylethanolamine N-methyl-transferase (PNMT)2001Journal of medicinal chemistry, Aug-16, Volume: 44, Issue:17
Synthesis and evaluation of 4-fluoro-8-substituted-2,3,4,5-tetrahydro-1H-2-benzazapines as selective inhibitors of phenylethanolamine N-methyltransferase versus the alpha(2)-adrenoceptor.
AID155320Inhibitory constant against human phenylethanolamine N-methyl-transferase over-expressed in Escherichia coli2001Bioorganic & medicinal chemistry letters, Jun-18, Volume: 11, Issue:12
Phenylethanolamine N-methyltransferase kinetics: bovine versus recombinant human enzyme.
AID282849Binding affinity to human PNMT V53A mutant2005Journal of medicinal chemistry, Nov-17, Volume: 48, Issue:23
Structural, mutagenic, and kinetic analysis of the binding of substrates and inhibitors of human phenylethanolamine N-methyltransferase.
AID234631Selectivity ratio (alpha2/PNMT)2001Journal of medicinal chemistry, Aug-16, Volume: 44, Issue:17
Synthesis and evaluation of 4-fluoro-8-substituted-2,3,4,5-tetrahydro-1H-2-benzazapines as selective inhibitors of phenylethanolamine N-methyltransferase versus the alpha(2)-adrenoceptor.
AID271162Selectivity for human PNMT over rat Adrenergic alpha-2 receptor2006Journal of medicinal chemistry, Sep-07, Volume: 49, Issue:18
Comparison of the binding of 3-fluoromethyl-7-sulfonyl-1,2,3,4-tetrahydroisoquinolines with their isosteric sulfonamides to the active site of phenylethanolamine N-methyltransferase.
AID313559Displacement of [3H]clonidine from adrenergic alpha-1 receptor in Sprague-Dawley rat cortex2008Bioorganic & medicinal chemistry, Jan-01, Volume: 16, Issue:1
Synthesis of 4,5,6,7-tetrahydrothieno[3,2-c]pyridines and comparison with their isosteric 1,2,3,4-tetrahydroisoquinolines as inhibitors of phenylethanolamine N-methyltransferase.
AID282850Binding affinity to human PNMT K57A mutant2005Journal of medicinal chemistry, Nov-17, Volume: 48, Issue:23
Structural, mutagenic, and kinetic analysis of the binding of substrates and inhibitors of human phenylethanolamine N-methyltransferase.
AID282851Binding affinity to human PNMT E219A mutant2005Journal of medicinal chemistry, Nov-17, Volume: 48, Issue:23
Structural, mutagenic, and kinetic analysis of the binding of substrates and inhibitors of human phenylethanolamine N-methyltransferase.
AID257556Displacement of [3H]clonidine from Adrenergic alpha-2 receptor2005Bioorganic & medicinal chemistry letters, Dec-01, Volume: 15, Issue:23
Inhibitors of phenylethanolamine N-methyltransferase devoid of alpha2-adrenoceptor affinity.
AID405520Inhibition of PNMT2008Journal of medicinal chemistry, Jul-10, Volume: 51, Issue:13
Recent developments in fragment-based drug discovery.
AID313560Selectivity of Ki for bovine PNMT over Ki for rat alpha-2 adrenoceptor2008Bioorganic & medicinal chemistry, Jan-01, Volume: 16, Issue:1
Synthesis of 4,5,6,7-tetrahydrothieno[3,2-c]pyridines and comparison with their isosteric 1,2,3,4-tetrahydroisoquinolines as inhibitors of phenylethanolamine N-methyltransferase.
AID176456Phenylethanolamine N-methyl-transferase inhibition determined as of [3H]epinephrine biosynthesis in rats at 50 mg/kg (po)1980Journal of medicinal chemistry, May, Volume: 23, Issue:5
Inhibitors of phenylethanolamine N-methyltransferase and epinephrine biosynthesis. 1. Chloro-substituted 1,2,3,4-tetrahydroisoquinolines.
AID36945Ability to inhibit binding of [3H]clonidine at the Alpha-2 adrenergic receptor1997Journal of medicinal chemistry, Dec-05, Volume: 40, Issue:25
Examination of the role of the acidic hydrogen in imparting selectivity of 7-(aminosulfonyl)-1,2,3,4-tetrahydroisoquinoline (SK&F 29661) toward inhibition of phenylethanolamine N-methyltransferase vs the alpha 2-adrenoceptor.
AID405505Inhibition of adrenergic alpha2 receptor2008Journal of medicinal chemistry, Jul-10, Volume: 51, Issue:13
Recent developments in fragment-based drug discovery.
AID243071Selectivity ratio for binding to alpha-2-adrenoceptor and phenylethanolamine N-Methyltransferase2005Journal of medicinal chemistry, Jan-13, Volume: 48, Issue:1
3-hydroxymethyl-7-(N-substituted aminosulfonyl)-1,2,3,4-tetrahydroisoquinoline inhibitors of phenylethanolamine N-methyltransferase that display remarkable potency and selectivity.
AID155306Inhibitory constant against bovine phenylethanolamine N-methyl-transferase2001Bioorganic & medicinal chemistry letters, Jun-18, Volume: 11, Issue:12
Phenylethanolamine N-methyltransferase kinetics: bovine versus recombinant human enzyme.
AID16300Calculated partition coefficient (clogP)2004Journal of medicinal chemistry, Jan-01, Volume: 47, Issue:1
Molecular recognition of sub-micromolar inhibitors by the epinephrine-synthesizing enzyme phenylethanolamine N-methyltransferase.
AID271161Displacement of [3H]clonidine from Sprague-Dawley rat cortex adrenergic alpha 2 receptor2006Journal of medicinal chemistry, Sep-07, Volume: 49, Issue:18
Comparison of the binding of 3-fluoromethyl-7-sulfonyl-1,2,3,4-tetrahydroisoquinolines with their isosteric sulfonamides to the active site of phenylethanolamine N-methyltransferase.
AID293031Selectivity for human PNMT over Sprague-Dawley rat adrenergic alpha-2 receptor2007Bioorganic & medicinal chemistry, Feb-01, Volume: 15, Issue:3
Exploring the active site of phenylethanolamine N-methyltransferase with 1,2,3,4-tetrahydrobenz[h]isoquinoline inhibitors.
AID293030Displacement of [3H]clonidine from adrenergic alpha2 receptor in Sprague-Dawley rat cortex membrane2007Bioorganic & medicinal chemistry, Feb-01, Volume: 15, Issue:3
Exploring the active site of phenylethanolamine N-methyltransferase with 1,2,3,4-tetrahydrobenz[h]isoquinoline inhibitors.
AID155333Dissociation constant(Ki) of compound was determined to measure PNMT-inhibitory potency1980Journal of medicinal chemistry, May, Volume: 23, Issue:5
Inhibitors of phenylethanolamine N-methyltransferase and epinephrine biosynthesis. 1. Chloro-substituted 1,2,3,4-tetrahydroisoquinolines.
AID37366Compound was tested in vitro for its affinity towards rat Alpha-2 adrenergic receptor1999Journal of medicinal chemistry, Sep-09, Volume: 42, Issue:18
Synthesis and biochemical evaluation of 3-fluoromethyl-1,2,3, 4-tetrahydroisoquinolines as selective inhibitors of phenylethanolamine N-methyltransferase versus the alpha(2)-adrenoceptor.
AID282852Binding affinity to human PNMT D267A mutant2005Journal of medicinal chemistry, Nov-17, Volume: 48, Issue:23
Structural, mutagenic, and kinetic analysis of the binding of substrates and inhibitors of human phenylethanolamine N-methyltransferase.
AID233623Ratio of binding affinity of PNMT to alpha-2 receptors.1999Journal of medicinal chemistry, Oct-21, Volume: 42, Issue:21
Enantiospecific synthesis of 3-fluoromethyl-, 3-hydroxymethyl-, and 3-chloromethyl-1,2,3,4-tetrahydroisoquinolines as selective inhibitors of phenylethanolamine N-methyltransferase versus the alpha(2)-adrenoceptor.
AID239072Inhibitory binding affinity for phenylethanolamine N-methyl-transferase (PNMT)2004Bioorganic & medicinal chemistry letters, Aug-16, Volume: 14, Issue:16
Phenylethanolamine N-methyltransferase inhibition: re-evaluation of kinetic data.
AID37094Binding affinity to alpha-2 adrenergic receptor by displacement of [3H]clonidine2001Journal of medicinal chemistry, Aug-16, Volume: 44, Issue:17
Synthesis and evaluation of 4-fluoro-8-substituted-2,3,4,5-tetrahydro-1H-2-benzazapines as selective inhibitors of phenylethanolamine N-methyltransferase versus the alpha(2)-adrenoceptor.
AID282848Binding affinity to human wild type his-tagged PNMT2005Journal of medicinal chemistry, Nov-17, Volume: 48, Issue:23
Structural, mutagenic, and kinetic analysis of the binding of substrates and inhibitors of human phenylethanolamine N-methyltransferase.
AID155146Inhibition of PNMT (Phenylethanolamine N-Methyltransferase) in vitro 1999Journal of medicinal chemistry, Aug-26, Volume: 42, Issue:17
Synthesis and evaluation of 3-trifluoromethyl-7-substituted-1,2,3, 4-tetrahydroisoquinolines as selective inhibitors of phenylethanolamine N-methyltransferase versus the alpha(2)-adrenoceptor.
AID42827Apparent permeability value through blood-brain barrier was evaluated using bovine brain microvessel endothelial cells (BBMEC)1999Journal of medicinal chemistry, Sep-09, Volume: 42, Issue:18
Synthesis and biochemical evaluation of 3-fluoromethyl-1,2,3, 4-tetrahydroisoquinolines as selective inhibitors of phenylethanolamine N-methyltransferase versus the alpha(2)-adrenoceptor.
AID35335Selectivity determined by Ki of alpha 2 receptor / Ki of PNMT1999Journal of medicinal chemistry, Aug-26, Volume: 42, Issue:17
Synthesis and evaluation of 3-trifluoromethyl-7-substituted-1,2,3, 4-tetrahydroisoquinolines as selective inhibitors of phenylethanolamine N-methyltransferase versus the alpha(2)-adrenoceptor.
AID239080In vitro binding affinity against human phenylethanolamine N-Methyltransferase2005Journal of medicinal chemistry, Jan-13, Volume: 48, Issue:1
3-hydroxymethyl-7-(N-substituted aminosulfonyl)-1,2,3,4-tetrahydroisoquinoline inhibitors of phenylethanolamine N-methyltransferase that display remarkable potency and selectivity.
AID155138Inhibition of Phenylethanolamine N-methyl-transferase (PNMT)1997Journal of medicinal chemistry, Dec-05, Volume: 40, Issue:25
Examination of the role of the acidic hydrogen in imparting selectivity of 7-(aminosulfonyl)-1,2,3,4-tetrahydroisoquinoline (SK&F 29661) toward inhibition of phenylethanolamine N-methyltransferase vs the alpha 2-adrenoceptor.
AID219806Inhibitory potency against alpha-2-adrenoceptor2004Journal of medicinal chemistry, Jan-01, Volume: 47, Issue:1
Molecular recognition of sub-micromolar inhibitors by the epinephrine-synthesizing enzyme phenylethanolamine N-methyltransferase.
AID221871Maximum inactive dose(MID) for decrease in norepinephrine (NE) / epinephrine(E) was measured in mice (po)1980Journal of medicinal chemistry, May, Volume: 23, Issue:5
Inhibitors of phenylethanolamine N-methyltransferase and epinephrine biosynthesis. 1. Chloro-substituted 1,2,3,4-tetrahydroisoquinolines.
AID155319In vitro inhibitory activity against human phenylethanolamine N-methyl-transferase1981Journal of medicinal chemistry, Jun, Volume: 24, Issue:6
Inhibitors of phenylethanolamine N-methyltransferase and epinephrine biosynthesis. 3. Bis[tetrahydroisoquinoline]s.
AID155329Inhibition of phenylethanolamine N-methyl-transferase from rabbit adrenal gland at 10e-6 M1980Journal of medicinal chemistry, May, Volume: 23, Issue:5
Inhibitors of phenylethanolamine N-methyltransferase and epinephrine biosynthesis. 1. Chloro-substituted 1,2,3,4-tetrahydroisoquinolines.
AID293029Binding affinity to human PNMT2007Bioorganic & medicinal chemistry, Feb-01, Volume: 15, Issue:3
Exploring the active site of phenylethanolamine N-methyltransferase with 1,2,3,4-tetrahydrobenz[h]isoquinoline inhibitors.
AID155337Ki ratio of human versus bovine phenylethanolamine N-methyl-transferase2001Bioorganic & medicinal chemistry letters, Jun-18, Volume: 11, Issue:12
Phenylethanolamine N-methyltransferase kinetics: bovine versus recombinant human enzyme.
AID257555Inhibitory activity against human PNMT2005Bioorganic & medicinal chemistry letters, Dec-01, Volume: 15, Issue:23
Inhibitors of phenylethanolamine N-methyltransferase devoid of alpha2-adrenoceptor affinity.
AID233871Selectivity expressed as the ratio of Ki of alpha-2-adrenoceptor to that of PNMT2004Journal of medicinal chemistry, Jan-01, Volume: 47, Issue:1
Molecular recognition of sub-micromolar inhibitors by the epinephrine-synthesizing enzyme phenylethanolamine N-methyltransferase.
AID35395Inhibition of [3H]clonidine binding to the rat alpha-2-adrenoceptor1999Bioorganic & medicinal chemistry letters, Feb-08, Volume: 9, Issue:3
Comparative molecular field analysis (CoMFA) models of phenylethanolamine N-methyltransferase (PNMT) and the alpha2-adrenoceptor: the development of new, highly selective inhibitors of PNMT.
AID155308Inhibitory potency against bovine phenylethanolamine N-Methyltransferase (PNMT)2004Journal of medicinal chemistry, Jan-01, Volume: 47, Issue:1
Molecular recognition of sub-micromolar inhibitors by the epinephrine-synthesizing enzyme phenylethanolamine N-methyltransferase.
AID239958Binding affinity against alpha 2 adrenergic receptor in rat cortex using [3H]clonidine as radioligand2005Bioorganic & medicinal chemistry letters, Feb-15, Volume: 15, Issue:4
Exploring the active site of phenylethanolamine N-methyltransferase with 3-hydroxyethyl- and 3-hydroxypropyl-7-substituted-1,2,3,4-tetrahydroisoquinolines.
AID221744Minimum active dose(MAD) for decrease in norepinephrine (NE) / epinephrine(E) was measured in mice (po)1980Journal of medicinal chemistry, May, Volume: 23, Issue:5
Inhibitors of phenylethanolamine N-methyltransferase and epinephrine biosynthesis. 1. Chloro-substituted 1,2,3,4-tetrahydroisoquinolines.
AID271160Binding affinity to human PNMT expressed in Escherichia coli by radiochemical assay2006Journal of medicinal chemistry, Sep-07, Volume: 49, Issue:18
Comparison of the binding of 3-fluoromethyl-7-sulfonyl-1,2,3,4-tetrahydroisoquinolines with their isosteric sulfonamides to the active site of phenylethanolamine N-methyltransferase.
AID155324In vitro inhibitory potency was measured against phenylethanolamine N-methyl-transferase1980Journal of medicinal chemistry, May, Volume: 23, Issue:5
Inhibitors of phenylethanolamine N-methyltransferase and epinephrine biosynthesis. 1. Chloro-substituted 1,2,3,4-tetrahydroisoquinolines.
AID244103Ratio of Ki for PNMT to that of alpha-2-adrenoceptor was determined2004Journal of medicinal chemistry, Aug-26, Volume: 47, Issue:18
Inhibitors of phenylethanolamine N-methyltransferase that are predicted to penetrate the blood-brain barrier: design, synthesis, and evaluation of 3-fluoromethyl-7-(N-substituted aminosulfonyl)-1,2,3,4-tetrahydroisoquinolines that possess low affinity tow
AID155328Inhibition of phenylethanolamine N-methyl-transferase from rabbit adrenal gland at 10e-4 M1980Journal of medicinal chemistry, May, Volume: 23, Issue:5
Inhibitors of phenylethanolamine N-methyltransferase and epinephrine biosynthesis. 1. Chloro-substituted 1,2,3,4-tetrahydroisoquinolines.
AID155145In vitro inhibition of PNMT (Phenylethanolamine N-Methyltransferase).1999Journal of medicinal chemistry, Oct-21, Volume: 42, Issue:21
Enantiospecific synthesis of 3-fluoromethyl-, 3-hydroxymethyl-, and 3-chloromethyl-1,2,3,4-tetrahydroisoquinolines as selective inhibitors of phenylethanolamine N-methyltransferase versus the alpha(2)-adrenoceptor.
AID239195In vitro inhibition of [3H]clonidine from alpha-2 adrenergic receptor of rat cortex2005Journal of medicinal chemistry, Jan-13, Volume: 48, Issue:1
3-hydroxymethyl-7-(N-substituted aminosulfonyl)-1,2,3,4-tetrahydroisoquinoline inhibitors of phenylethanolamine N-methyltransferase that display remarkable potency and selectivity.
AID155323Inhibition of rabbit adrenal phenylethanolamine N-methyl-transferase1981Journal of medicinal chemistry, Jun, Volume: 24, Issue:6
Inhibitors of phenylethanolamine N-methyltransferase and epinephrine biosynthesis. 3. Bis[tetrahydroisoquinoline]s.
AID977610Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB2005Journal of medicinal chemistry, Nov-17, Volume: 48, Issue:23
Structural, mutagenic, and kinetic analysis of the binding of substrates and inhibitors of human phenylethanolamine N-methyltransferase.
AID1811Experimentally measured binding affinity data derived from PDB2005Journal of medicinal chemistry, Nov-17, Volume: 48, Issue:23
Structural, mutagenic, and kinetic analysis of the binding of substrates and inhibitors of human phenylethanolamine N-methyltransferase.
AID1797149alpha-Adrenoceptor Radioligand Binding Assay from Article 10.1021/jm0205752: \\Molecular recognition of sub-micromolar inhibitors by the epinephrine-synthesizing enzyme phenylethanolamine N-methyltransferase.\\2004Journal of medicinal chemistry, Jan-01, Volume: 47, Issue:1
Molecular recognition of sub-micromolar inhibitors by the epinephrine-synthesizing enzyme phenylethanolamine N-methyltransferase.
AID1796978Radiochemical Assay of PNMT Inhibitors from Article 10.1021/jm060466d: \\Comparison of the binding of 3-fluoromethyl-7-sulfonyl-1,2,3,4-tetrahydroisoquinolines with their isosteric sulfonamides to the active site of phenylethanolamine N-methyltransferase.\\2006Journal of medicinal chemistry, Sep-07, Volume: 49, Issue:18
Comparison of the binding of 3-fluoromethyl-7-sulfonyl-1,2,3,4-tetrahydroisoquinolines with their isosteric sulfonamides to the active site of phenylethanolamine N-methyltransferase.
AID1797148Radiochemical Assay for PNMT Activity from Article 10.1021/jm0205752: \\Molecular recognition of sub-micromolar inhibitors by the epinephrine-synthesizing enzyme phenylethanolamine N-methyltransferase.\\2004Journal of medicinal chemistry, Jan-01, Volume: 47, Issue:1
Molecular recognition of sub-micromolar inhibitors by the epinephrine-synthesizing enzyme phenylethanolamine N-methyltransferase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (75)

TimeframeStudies, This Drug (%)All Drugs %
pre-199047 (62.67)18.7374
1990's14 (18.67)18.2507
2000's14 (18.67)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (2.53%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other77 (97.47%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]