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.'
ID Source | ID |
---|---|
PubMed CID | 9377 |
CHEMBL ID | 1200705 |
SCHEMBL ID | 221647 |
MeSH ID | M0015730 |
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.) |
Excerpt | Reference | Relevance |
---|---|---|
"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 |
Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
---|---|---|---|---|---|---|---|
67.9K protein | Vaccinia virus | Potency | 14.1254 | 0.0001 | 8.4406 | 100.0000 | AID720580 |
peripheral myelin protein 22 | Rattus norvegicus (Norway rat) | Potency | 9.0743 | 0.0056 | 12.3677 | 36.1254 | AID624032 |
histone acetyltransferase KAT2A isoform 1 | Homo sapiens (human) | Potency | 7.0795 | 0.2512 | 15.8432 | 39.8107 | AID504327 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
---|---|---|---|---|---|---|---|
trace amine-associated receptor 1 | Homo sapiens (human) | IC50 (µMol) | 8.8445 | 0.1571 | 3.8257 | 9.3940 | AID686984 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
---|---|---|---|---|---|---|---|
trace amine-associated receptor 1 | Homo sapiens (human) | EC50 (µMol) | 1.4450 | 0.0685 | 2.1184 | 9.9700 | AID686985 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID504749 | qHTS profiling for inhibitors of Plasmodium falciparum proliferation | 2011 | Science (New York, N.Y.), Aug-05, Volume: 333, Issue:6043 | Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets. |
AID1296008 | Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening | 2020 | SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1 | Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening. |
AID1346987 | P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen | 2019 | Molecular pharmacology, 11, Volume: 96, Issue:5 | A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. |
AID1346986 | P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen | 2019 | Molecular pharmacology, 11, Volume: 96, Issue:5 | A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. |
AID1159550 | Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening | 2015 | Nature cell biology, Nov, Volume: 17, Issue:11 | 6-Phosphogluconate dehydrogenase links oxidative PPP, lipogenesis and tumour growth by inhibiting LKB1-AMPK signalling. |
AID588519 | A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities | 2011 | Antiviral research, Sep, Volume: 91, Issue:3 | High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors. |
AID540299 | A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis | 2010 | Bioorganic & 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. |
AID977599 | Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM | 2013 | Molecular pharmacology, Jun, Volume: 83, Issue:6 | Structure-based identification of OATP1B1/3 inhibitors. |
AID977602 | Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM | 2013 | Molecular 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] |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 0 (0.00) | 18.7374 |
1990's | 0 (0.00) | 18.2507 |
2000's | 0 (0.00) | 29.6817 |
2010's | 6 (85.71) | 24.3611 |
2020's | 1 (14.29) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 0 (0.00%) | 5.53% |
Reviews | 1 (14.29%) | 6.00% |
Case Studies | 0 (0.00%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 6 (85.71%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |