| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| Other Sizes |
| Targets |
The primary therapeutic target is the adrenergic nervous system in the eye. Hydroxyamphetamine causes the release of norepinephrine from postganglionic adrenergic nerve terminals, which then stimulates both alpha- and beta-adrenergic receptors on the iris dilator muscle, leading to mydriasis.
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| ln Vitro |
In vitro activity is primarily studied in isolated tissues (e.g., rat vas deferens or rabbit iris). Hydroxyamphetamine (1-100 microM) produces a concentration-dependent contraction by releasing endogenous norepinephrine. This effect is blocked by prior depletion of norepinephrine with reserpine, confirming its indirect mechanism of action.
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| ln Vivo |
In vivo, the primary activity is mydriasis (pupil dilation) following topical ocular application. Instillation of one to two drops of a 1% solution into the eye produces maximal dilation within 20-60 minutes, lasting for several hours. This effect is used to aid in the examination of the retina and optic nerve and to diagnose Horner‘s syndrome.
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| Enzyme Assay |
A non-cellular assay is not directly applicable due to its indirect mechanism. However, HPLC-based analytical methods exist to quantify the parent drug in biological fluids. Standard chemical stability tests involve dissolving the compound in various buffers to determine its degradation kinetics under different pH and temperature conditions.
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| Cell Assay |
The diagnostic pharmacological effect is confirmed in vivo rather than in vitro. However, to verify potency, rabbit iris sphincter muscles are mounted in an organ bath and exposed to Hydroxyamphetamine (0.1-100 microM), and the contractile force is measured. The response is compared to that of norepinephrine to confirm the indirect nature of the agonist activity.
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| Animal Protocol |
The primary animal model is the rat or rabbit for ophthalmic studies. Following baseline pupil diameter measurement, a single drop of Hydroxyamphetamine HBr solution (e.g., 0.5-2%) is applied to the ocular surface. Pupil diameter is measured using a ruler or calipers at multiple time points (0.5, 1, 2, 4 hours) post-instillation to determine the magnitude and duration of the mydriatic effect.
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| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion
For topical use only (ophthalmic use). For topical use only (ophthalmic use). For topical use only (ophthalmic use). For topical use only (ophthalmic use). Metabolites/Metabolic Substances For topical use only (ophthalmic use). 4-Hydroxyamphetamine is a known metabolite of amphetamine in the human body. Following ocular topical application, Hydroxyamphetamine acts locally with minimal systemic absorption. If absorbed, it is metabolized in the liver primarily by monoamine oxidase (MAO) and catechol-O-methyltransferase (COMT) to inactive metabolites, which are excreted in the urine. It has a short plasma half-life of approximately 1-2 hours. |
| Toxicity/Toxicokinetics |
Protein Binding
For topical use only (ophthalmic use). When used as directed (topical ocular), Hydroxyamphetamine is generally safe, with minor and temporary side effects including local stinging, burning, blurred vision, photophobia, and eye redness. Systemic toxicity is rare due to low absorption but could cause tachycardia, hypertension, and headache in sensitive individuals. |
| References |
[1]. Mansoor Mughal, et al. Current pharmacologic testing for Horner syndrome. Curr Neurol Neurosci Rep. 2009 Sep;9(5):384-9.
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| Additional Infomation |
4-(2-aminopropyl)phenol belongs to the amphetamine class of drugs. Hydroxypropylamine is a derivative of amphetamine. Hydroxypropylamine is primarily used as topical eye drops for diagnostic purposes. It is an indirect sympathomimetic drug that can cause pupillary dilation before diagnostic tests. Its minor side effects include: altered color vision, night blindness, dry mouth, headache, increased sensitivity of the eyes to sunlight, muscle stiffness or tightness, and temporary eye irritation. The main use of hydroxypropylamine as eye drops is for diagnosing Horner's syndrome, a syndrome characterized by nerve damage. Hydroxypropylamine is an adrenergic receptor agonist. Its mechanism of action is as an adrenergic agonist. 4-(2-aminopropyl)phenol has been reported in Senegalia berlandieri, and relevant data are available. Hydroxypropylamine is an indirect-acting sympathomimetic amine with adrenergic properties. When amphetamine is applied topically to the eye, it stimulates postganglionic adrenergic nerves to release norepinephrine, thereby stimulating α and β adrenergic receptors. Local α-receptor stimulation includes pupillary dilation, increased aqueous humor flow, and vasoconstriction; while β-receptor stimulation includes ciliary muscle relaxation and decreased aqueous humor production. Amphetamine metabolites have sympathomimetic effects. It is sometimes referred to as α-methyltyramine, and may also refer to the meta-isomer jeopardine. Drug Indications Used as a mydriatic (pupil dilator) for the diagnosis of ocular neuropathy. Mechanism of Action Amphetamine hydrobromide is an indirect-acting sympathomimetic drug that induces the release of norepinephrine from adrenergic nerve endings, leading to pupillary dilation.
Hydroxyamphetamine has been approved by the FDA for diagnostic ophthalmic use to differentiate between central and peripheral Horner‘s syndrome. A positive test (marked dilation) indicates a peripheral lesion. It is not used therapeutically for long-term conditions. It is available under brand names like Paredrine. |
| Molecular Formula |
C9H13NO
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|---|---|
| Molecular Weight |
151.21
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| Exact Mass |
151.1
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| CAS # |
103-86-6
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| Related CAS # |
Hydroxyamphetamine hydrobromide;306-21-8;Hydroxyamphetamine hydrochloride;876-26-6
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| PubChem CID |
3651
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| Appearance |
Typically exists as solid at room temperature
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| Density |
1.07g/cm3
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| Boiling Point |
279.2ºC at 760mmHg
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| Flash Point |
122.7ºC
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| LogP |
1.982
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
11
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| Complexity |
108
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC(CC1=CC=C(C=C1)O)N
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| InChi Key |
GIKNHHRFLCDOEU-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C9H13NO/c1-7(10)6-8-2-4-9(11)5-3-8/h2-5,7,11H,6,10H2,1H3
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| Chemical Name |
4-(2-aminopropyl)phenol
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO: 100 mg/mL (661.33 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (16.53 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (16.53 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (16.53 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.6133 mL | 33.0666 mL | 66.1332 mL | |
| 5 mM | 1.3227 mL | 6.6133 mL | 13.2266 mL | |
| 10 mM | 0.6613 mL | 3.3067 mL | 6.6133 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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