Page last updated: 2024-12-05

hydroxyamphetamine hydrobromide

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

Hydroxyamphetamine hydrobromide is a synthetic sympathomimetic amine that acts as a direct-acting agonist of adrenergic receptors. It is used in research to study the function of the sympathetic nervous system and as a diagnostic tool for certain medical conditions. The compound has been investigated for its potential as a treatment for various conditions, including narcolepsy, attention-deficit/hyperactivity disorder, and obesity. However, its use has been limited due to its potential for adverse effects, such as increased blood pressure, heart rate, and anxiety. The compound's synthesis involves a multi-step process that starts with the reaction of benzaldehyde with nitroethane to form a nitrostyrene derivative. This derivative is then reduced to the corresponding amine, followed by a series of reactions to introduce the hydroxy group. Hydroxyamphetamine hydrobromide has been used in research to study the effects of adrenergic agonists on various tissues and organs. For example, it has been used to investigate the role of the sympathetic nervous system in the regulation of blood pressure, heart rate, and blood flow. The compound has also been used to study the mechanisms of action of various drugs that target the sympathetic nervous system, such as beta-blockers and sympathomimetics. Despite its potential as a therapeutic agent, hydroxyamphetamine hydrobromide has a limited clinical application due to its potential for adverse effects. Studies have shown that the compound can cause a variety of side effects, including headache, dizziness, nausea, and anxiety. In some cases, the compound can also cause more serious side effects, such as hypertension, tachycardia, and arrhythmias. However, it remains an important research tool for understanding the function of the sympathetic nervous system and for developing new therapies for conditions that affect this system.'

Cross-References

ID SourceID
PubMed CID9377
CHEMBL ID1200705
SCHEMBL ID221647
MeSH IDM0015730

Synonyms (84)

Synonym
paredrine hydrobromide
.beta.-(p-hydroxyphenyl)isopropylamine hydrobromide
nsc-61065
wln: zy1&1r dq &eh
3-(p-hydroxyphenyl)-2-aminopropane hydrobromide
p-(2-aminopropyl)phenol hydrobromide
p-(2-aminopropyl)phenyl hydrobromide
phenol, hydrobromide
2-amino-1-(4-hydroxyphenyl)propane hydrobromide
hydroxyamphetamine hydrobromide
306-21-8
nsc61065
p-hydroxyamphetamine hydrobromide
component of paredrine
predrolon
mycadrine
1-p-hydroxyphenyl-2-aminopropane hydrobromide
(+-)-paredrine hydrobromide
nsc 61065
phenol, p-(2-aminopropyl)-, hydrobromide
hydroxyamfetamin hydrobromid
einecs 206-181-4
4-(2-aminopropyl)phenol hydrobromide
(+-)-p-(2-aminopropyl)phenol hydrobromide
beta-(p-hydroxyphenyl)isopropylamine hydrobromide
phenol, 4-(2-aminopropyl)-, hydrobromide
phenol, p-(2-aminopropyl)-, hydrobromide, (+-)-
dl-p-(2-aminopropyl)phenol hydrobromide
paredrine (tn)
hydroxyamphetamine hydrobromide (usp)
D04473
NCGC00095233-01
NCGC00095233-02
SPECTRUM211425
hydroxyamfetamine hydrobromide
oxamphetamine hydrobromide
hydroxyamphetamine hbr
phenol, 4-(2-aminopropyl)-, hbr
CHEMBL1200705
hyroxyamfetamine hydrobromide
hydroxyamfetamine hbr
HMS1923C15
4-(2-aminopropyl)phenol;hydrobromide
hydrobromide, hydroxyamphetamine
hydroxyamphetamine hydrobromide [usp]
59ig47sz0e ,
unii-59ig47sz0e
cas-306-21-8
tox21_111487
dtxsid0045961 ,
dtxcid8025961
nsc-760066
pharmakon1600-00211425
nsc760066
(+/-)-4-hydroxyamphetamine hydrobromide
MLS002320672
MLS002320674
smr001338820
smr001338818
(+)-4-hydroxyamphetamine hydrobromide
140-36-3
phenol,4-(2-aminopropyl)-, hydrobromide (1:1)
cid_9377
SCHEMBL221647
(+/-)-p-(2-aminopropyl)phenol hydrobromide
hydroxyamfetamine hydrobromide [mart.]
hydroxyamphetamine hydrobromide [usp-rs]
hydroxyamphetamine hydrobromide [usp monograph]
hydroxyamphetamine hydrobromide [orange book]
(+/-)-p-(2-aminopropyl)phenol hbr
hydroxyamphetamine hydrobromide [mi]
paremyd component hydroxyamphetamine hydrobromide
hydroxyamfetamine hydrobromide [who-dd]
hydroxyamphetamine hydrobromide component of paremyd
hydroxyamphetamine hydrobromide [vandf]
CCG-213716
RZCJLMTXBMNRAD-UHFFFAOYSA-N
rac. 4-hydroxy-alpha-methylphenethylamine hydrobromide
Q27261708
EN300-7866760
AKOS040758032
hydroxyamphetamine hydrobromide (usp-rs)
hydroxyamphetamine hydrobromide (usp monograph)
hydroxyamfetamine hydrobromide (mart.)

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (5)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
67.9K proteinVaccinia virusPotency14.12540.00018.4406100.0000AID720580
peripheral myelin protein 22Rattus norvegicus (Norway rat)Potency9.07430.005612.367736.1254AID624032
histone acetyltransferase KAT2A isoform 1Homo sapiens (human)Potency7.07950.251215.843239.8107AID504327
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
trace amine-associated receptor 1Homo sapiens (human)IC50 (µMol)8.84450.15713.82579.3940AID686984
[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)
trace amine-associated receptor 1Homo sapiens (human)EC50 (µMol)1.44500.06852.11849.9700AID686985
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (9)

Assay IDTitleYearJournalArticle
AID504749qHTS profiling for inhibitors of Plasmodium falciparum proliferation2011Science (New York, N.Y.), Aug-05, Volume: 333, Issue:6043
Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1159550Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening2015Nature cell biology, Nov, Volume: 17, Issue:11
6-Phosphogluconate dehydrogenase links oxidative PPP, lipogenesis and tumour growth by inhibiting LKB1-AMPK signalling.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID977599Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID977602Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's6 (85.71)24.3611
2020's1 (14.29)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%
Reviews1 (14.29%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other6 (85.71%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]