Details
Stereochemistry | RACEMIC |
Molecular Formula | C9H13NO |
Molecular Weight | 151.2056 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(N)CC1=CC=C(O)C=C1
InChI
InChIKey=GIKNHHRFLCDOEU-UHFFFAOYSA-N
InChI=1S/C9H13NO/c1-7(10)6-8-2-4-9(11)5-3-8/h2-5,7,11H,6,10H2,1H3
Molecular Formula | C9H13NO |
Molecular Weight | 151.2056 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
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 Date6.967296E11 |
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 |
---|---|---|
The correlation of phenylephrine 1% with hydroxyamphetamine 1% in Horner's syndrome. | 2004 Apr |
|
Determination of amphetamine, methamphetamine, and hydroxyamphetamine derivatives in urine by gas chromatography-mass spectrometry and its relation to CYP2D6 phenotype of drug users. | 2007 Jan-Feb |
|
p-Hydroxyamphetamine causes prepulse inhibition disruptions in mice: contribution of dopamine neurotransmission. | 2010 Dec 25 |
|
Central administration of p-hydroxyamphetamine produces a behavioral stimulant effect in rodents: evidence for the involvement of dopaminergic systems. | 2010 Feb |
|
New meconium biomarkers of prenatal methamphetamine exposure increase identification of affected neonates. | 2010 May |
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
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 18:56:03 UTC 2023
by
admin
on
Fri Dec 15 18:56:03 UTC 2023
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Record UNII |
FQR280JW2N
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Record Status |
Validated (UNII)
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NCI_THESAURUS |
C29747
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NDF-RT |
N0000000122
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NDF-RT |
N0000175883
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Code System | Code | Type | Description | ||
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4-Hydroxyamphetamine
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DB09352
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136
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DTXSID3023134
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100000084199
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103-86-6
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203-152-8
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C61787
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1394
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3651
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SUB08075MIG
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D010136
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CHEMBL1546
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m6117
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170995
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7839
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FQR280JW2N
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FQR280JW2N
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1518-86-1
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SUPERSEDED |
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SALT/SOLVATE -> PARENT | |||
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ENANTIOMER -> RACEMATE |
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PARENT -> METABOLITE |
MINOR
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PARENT -> METABOLITE |
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PARENT -> METABOLITE ACTIVE |
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ACTIVE MOIETY |