Details
Stereochemistry | RACEMIC |
Molecular Formula | C9H13NO.BrH |
Molecular Weight | 232.118 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Br.CC(N)CC1=CC=C(O)C=C1
InChI
InChIKey=RZCJLMTXBMNRAD-UHFFFAOYSA-N
InChI=1S/C9H13NO.BrH/c1-7(10)6-8-2-4-9(11)5-3-8;/h2-5,7,11H,6,10H2,1H3;1H
Hydroxyamphetamine is a derivative of amphetamines. Hydroxyamphetamine is intended mainly as local eye drops for diagnostic purposes. It is indirect sympathomimetic agent which cause dilation of the eye pupil before diagnostic test. Among the minor side effects from its use are: change in color vision, difficulty seeing at night, dry mouth, headache, increased sensitivity of eyes to sunlight, muscle stiffness or tightness and temporary stinging in the eyes. The main use of hydroxyamphetamines as eye drops is the diagnosis of Horner's syndrome which is characterized by nerve lesions. Hydroxyamphetamine hydrobromide is a component of FDA approved brand drug - Paremyd sterile ophthalmic solution (Hydroxyamphetamine hydrobromide, USP 1.0%, Tropicamide, USP 0.25%). Hydroxyamphetamine is an indirect-acting sympathomimetic, while tropicamide acts as a parasympatholytic.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1202363 | https://www.ncbi.nlm.nih.gov/pubmed/24113072
Curator's Comment: The blood-brain barrier is permutle to Hydroxyamphetamine in rats. Hydroxyamphetamine is CNS active
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Diagnostic | Paremyd Approved UsePAREMYD Solution is indicated for mydriasis in routine diagnostic procedures and in conditions
where short-term pupil dilation is desired. PAREMYD provides clinically significant mydriasis with
partial cycloplegia. Launch Date1992 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.8 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/13143480/ |
10 mg/kg bw single, intravenous dose: 10 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered: |
HYDROXYAMPHETAMINE plasma | Canis lupus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/13143480/ |
10 mg/kg bw single, intravenous dose: 10 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered: |
HYDROXYAMPHETAMINE plasma | Canis lupus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/13143480/ |
10 mg/kg bw single, intravenous dose: 10 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered: |
HYDROXYAMPHETAMINE plasma | Canis lupus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
PubMed
Title | Date | PubMed |
---|---|---|
Hydroxyamphetamine drops for Horner's syndrome. | 2001 Aug |
|
Hydroxyamphetamine increases intraocular pressure in rabbits. | 2001 Feb |
|
Determination of amphetamine and its metabolite p-hydroxyamphetamine in rat urine by reversed-phase high-performance liquid chromatography after dabsyl derivatization. | 2001 Nov |
|
Horner syndrome. | 2003 Dec |
|
Trace amine-associated receptor 1 displays species-dependent stereoselectivity for isomers of methamphetamine, amphetamine, and para-hydroxyamphetamine. | 2007 Apr |
|
Novel biomarkers of prenatal methamphetamine exposure in human meconium. | 2009 Feb |
|
p-Hydroxyamphetamine causes prepulse inhibition disruptions in mice: contribution of dopamine neurotransmission. | 2010 Dec 25 |
Patents
Sample Use Guides
Mydriasis: Ophthalmic: Instill 1 to 2 drops into conjunctival sac(s)
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28115274
SH-SY5Y neurons were incubated with Hydroxyamphetamine (concentration range 0-10mM) for 24 or 48h, and the viability was determined by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) and lactate dehydrogenase (LDH) leakage assays.. For Hydroxyamphetamine the TC50 was not reached in the tested concentration range. Hydroxyamphetamine at 8.00mM originated few late apoptotic cells
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C29747
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ACTIVE MOIETY
SUBSTANCE RECORD