Page last updated: 2024-12-05

p-hydroxyamphetamine

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

Description

p-Hydroxyamphetamine: Amphetamine metabolite with sympathomimetic effects. It is sometimes called alpha-methyltyramine, which may also refer to the meta isomer, gepefrine. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID3651
CHEMBL ID1546
CHEBI ID103855
SCHEMBL ID125440
MeSH IDM0015728

Synonyms (89)

Synonym
BRD-A80871782-004-01-0
phenol,4-(2-aminopropyl)-
paredrine
oksamfetamin
oxamphetamine
wln: z3r dq
p-hydroxy-.alpha.-methylphenethylamine
4-hydroxy-.alpha.-methylphenethylamine
dl-p-(2-aminopropyl)phenol
oxamfetamin
pulsoton
4-(2-aminopropyl)phenol
nsc170995
paredrinex
4-hydroxyamphetamine
nsc-170995
p-(2-aminopropyl)phenol
phenol, p-(2-aminopropyl)-
pedrolon
phenol, 4-(2-aminopropyl)-
norveritol
103-86-6
nov-pholedrin
p-hydroxyamphetamine
paradrine
.alpha.-methyltyramine
norpholedrine
2-amino-1-(p-hydroxyphenyl)propane
1-p-hydroxyphenyl-2-propylamine
oxamphetaminium
hydroxyamphetamide
SPECTRUM_001243
PDSP2_001091
nsc 170995
brn 2413849
einecs 203-152-8
phenol, p-(2-aminopropyl)-, (.+/-.)-
phenol, 4-(2-aminopropyl)-, (.+/-.)-
PDSP1_001107
NCGC00178433-01
SPECTRUM5_001674
BSPBIO_002853
hydroxyamfetamine
KBIO3_002073
KBIOSS_001723
KBIO2_004291
KBIOGR_001807
KBIO2_006859
KBIO2_001723
SPECTRUM4_001174
SPECTRUM3_001037
CHEMBL1546
racemic p-hydroxyamphetamine
dl-4-hydroxyamphetamine
dl-p-hydroxyamphetamine
AKOS000155358
1518-86-1
CHEBI:103855
hydroxyamphetamine,(+/-)
bdbm81459
cas_103-86-6
nsc_3651
unii-fqr280jw2n
fqr280jw2n ,
3-13-00-01709 (beilstein handbook reference)
hydroxyamfetamine [inn:ban]
EN300-53926
AKOS017269170
hydroxyamphetamine [vandf]
hydroxyamfetamine [inn]
hydroxyamphetamine [mi]
hydroxyamfetamine [who-dd]
(+/-)-p-(2-aminopropyl)phenol
oh-a
SCHEMBL125440
CS-4687
4-(2-amino-propyl)-phenol
1-(4-hydroxyphenyl)propane-2-amine
predrolon (salt/mix)
HY-B1098
AB01563354_01
(+/-)-4-hydroxyamphetamine
DTXSID3023134
Z57102382
BS-13447
DB09352
(rs)-4-hydroxyamphetamine
Q5955531
NCGC00178433-02

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"A drug registry was established at Southern California College of Optometry (SCCO) to study use rates and incidence of adverse side effects of the nine pharmaceutical agents in the California optometry law."( Use of diagnostic pharmaceutical agents and incidence of adverse effects.
Applebaum, M; Jaanus, SD, 1983
)
0.27
" The findings suggest that 4-substituted amphetamines exhibit a wide variation in their effects on maternal toxicity and pregnancy wastage, and produce adverse effects on parturition, pup survival, and postnatal development."( Developmental toxicity of 4-substituted amphetamines in mice.
Buttar, HS; Foster, BC; Moffatt, JH,
)
0.13

Compound-Compound Interactions

ExcerptReferenceRelevance
" Twelve healthy men were administered a single oral dose of ritobegron (20 mg) alone or in combination with probenecid 2 hours before administration of ritobegron."( Investigation of Drug-Drug Interactions Between Ritobegron, a Selective β3 -Adrenoceptor Agonist, With Probenecid in Healthy Men.
Abe, Y; Endo, T; Furihata, T; Kanazawa, T; Kobayashi, M; Nakano, Y, 2016
)
0.43

Bioavailability

ExcerptReferenceRelevance
" The bioavailability of KUC-7322 was estimated to be 4%."( Absorption, disposition, metabolism, and excretion of ritobegron (KUC-7483), a novel selective β3-adrenoceptor agonist, in rats.
Abe, Y; Endo, T; Kobayashi, M; Murakami, M; Ota, E, 2014
)
0.4
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
amphetaminesAmines that constitute a class of central nervous system stimulants based on the structure of the parent amphetamine 1-phenylpropan-2-amine.
[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 (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Beta-secretase 1Homo sapiens (human)IC50 (µMol)100.00000.00061.619410.0000AID318155
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Beta-secretase 1Homo sapiens (human)Kd800.00000.04000.04000.0400AID318154
Trace amine-associated receptor 1Rattus norvegicus (Norway rat)EC50 (µMol)0.05050.01390.42632.0440AID1442356; AID635290
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (16)

Processvia Protein(s)Taxonomy
proteolysisBeta-secretase 1Homo sapiens (human)
membrane protein ectodomain proteolysisBeta-secretase 1Homo sapiens (human)
response to lead ionBeta-secretase 1Homo sapiens (human)
protein processingBeta-secretase 1Homo sapiens (human)
amyloid-beta formationBeta-secretase 1Homo sapiens (human)
amyloid precursor protein catabolic processBeta-secretase 1Homo sapiens (human)
positive regulation of neuron apoptotic processBeta-secretase 1Homo sapiens (human)
amyloid-beta metabolic processBeta-secretase 1Homo sapiens (human)
detection of mechanical stimulus involved in sensory perception of painBeta-secretase 1Homo sapiens (human)
prepulse inhibitionBeta-secretase 1Homo sapiens (human)
cellular response to copper ionBeta-secretase 1Homo sapiens (human)
cellular response to manganese ionBeta-secretase 1Homo sapiens (human)
presynaptic modulation of chemical synaptic transmissionBeta-secretase 1Homo sapiens (human)
signaling receptor ligand precursor processingBeta-secretase 1Homo sapiens (human)
cellular response to amyloid-betaBeta-secretase 1Homo sapiens (human)
amyloid fibril formationBeta-secretase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
amyloid-beta bindingBeta-secretase 1Homo sapiens (human)
endopeptidase activityBeta-secretase 1Homo sapiens (human)
aspartic-type endopeptidase activityBeta-secretase 1Homo sapiens (human)
protein bindingBeta-secretase 1Homo sapiens (human)
peptidase activityBeta-secretase 1Homo sapiens (human)
beta-aspartyl-peptidase activityBeta-secretase 1Homo sapiens (human)
enzyme bindingBeta-secretase 1Homo sapiens (human)
protein serine/threonine kinase bindingBeta-secretase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (20)

Processvia Protein(s)Taxonomy
lysosomeBeta-secretase 1Homo sapiens (human)
endosomeBeta-secretase 1Homo sapiens (human)
early endosomeBeta-secretase 1Homo sapiens (human)
late endosomeBeta-secretase 1Homo sapiens (human)
multivesicular bodyBeta-secretase 1Homo sapiens (human)
endoplasmic reticulum lumenBeta-secretase 1Homo sapiens (human)
Golgi apparatusBeta-secretase 1Homo sapiens (human)
trans-Golgi networkBeta-secretase 1Homo sapiens (human)
plasma membraneBeta-secretase 1Homo sapiens (human)
synaptic vesicleBeta-secretase 1Homo sapiens (human)
cell surfaceBeta-secretase 1Homo sapiens (human)
endosome membraneBeta-secretase 1Homo sapiens (human)
membraneBeta-secretase 1Homo sapiens (human)
axonBeta-secretase 1Homo sapiens (human)
dendriteBeta-secretase 1Homo sapiens (human)
neuronal cell bodyBeta-secretase 1Homo sapiens (human)
membrane raftBeta-secretase 1Homo sapiens (human)
recycling endosomeBeta-secretase 1Homo sapiens (human)
Golgi-associated vesicle lumenBeta-secretase 1Homo sapiens (human)
hippocampal mossy fiber to CA3 synapseBeta-secretase 1Homo sapiens (human)
endosomeBeta-secretase 1Homo sapiens (human)
plasma membraneBeta-secretase 1Homo sapiens (human)
trans-Golgi networkBeta-secretase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (6)

Assay IDTitleYearJournalArticle
AID1442356Agonist activity at rat N-terminal FLAG-tagged TAAR1 expressed in HEK293 cells assessed as [3H]cAMP accumulation measured after 1 hr2017Journal of medicinal chemistry, 04-13, Volume: 60, Issue:7
The 2014 Philip S. Portoghese Medicinal Chemistry Lectureship: The "Phenylalkylaminome" with a Focus on Selected Drugs of Abuse.
AID635290Activation of rat TAAR1 expressed in HEK293 cells assessed as accumulation of [3H]cAMP after 1 hr by competitive binding assay2011Bioorganic & medicinal chemistry, Dec-01, Volume: 19, Issue:23
Trace amine-associated receptor 1 is a stereoselective binding site for compounds in the amphetamine class.
AID318154Binding affinity to BACE1 by surface plasmon resonance method2008Bioorganic & medicinal chemistry letters, Feb-15, Volume: 18, Issue:4
Tyramine fragment binding to BACE-1.
AID318155Inhibition of BACE12008Bioorganic & medicinal chemistry letters, Feb-15, Volume: 18, Issue:4
Tyramine fragment binding to BACE-1.
AID1135266Inhibition of norepinephrine release in sc dosed mouse heart administered 60 mins before [3H]-norepinephrine challenge1977Journal of medicinal chemistry, May, Volume: 20, Issue:5
N-(2,4,5-Trihydroxyphenehtyl)normetazocine, a potential irreversible inhibitor of the narcotic receptor.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (195)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990130 (66.67)18.7374
1990's27 (13.85)18.2507
2000's17 (8.72)29.6817
2010's17 (8.72)24.3611
2020's4 (2.05)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 (%)
Trials6 (2.88%)5.53%
Reviews9 (4.33%)6.00%
Case Studies12 (5.77%)4.05%
Observational0 (0.00%)0.25%
Other181 (87.02%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (2)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
Open Label, Randomized, Single-dose, Five-way Crossover Study to Investigate the Regional Drug Absorption of 80 mg KUC-7483 CL Administered Via an Enterion™ Capsule Compared to an Immediate Release Formulation in Healthy Male Volunteers. [NCT02259920]Phase 113 participants (Actual)Interventional2003-12-31Completed
A Double-blinded, Randomised, Placebo Controlled, Five-way Crossover Study With One Positive Control (Open-label) (Moxifloxacin) to Assess the Influence of Oral Single Dose KUC 7483 BS (40 mg, 80 mg, 160 mg, 320 mg) on the QT/QTc Interval of the ECG in He [NCT02256735]Phase 139 participants (Actual)Interventional2005-08-31Completed
[information is prepared from clinicaltrials.gov, extracted Sep-2024]