Hydroxyamphetamine (4-Hydroxyamphetamine) is a sympathomimetic agent that stimulates the sympathetic nervous system. Hydroxyamphetamine HBr may be used as eye drops to dilate the pupils.

Physicochemical Properties

Molecular Formula	C9H13NO
Molecular Weight	151.21
Exact Mass	151.1
CAS #	103-86-6
Related CAS #	Hydroxyamphetamine hydrobromide;306-21-8;Hydroxyamphetamine hydrochloride;876-26-6
PubChem CID	3651
Appearance	Typically exists as solid at room temperature
Density	1.07g/cm3
Boiling Point	279.2ºC at 760mmHg
Flash Point	122.7ºC
LogP	1.982
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	2
Heavy Atom Count	11
Complexity	108
Defined Atom Stereocenter Count	0
SMILES	CC(CC1=CC=C(C=C1)O)N
InChi Key	GIKNHHRFLCDOEU-UHFFFAOYSA-N
InChi Code	InChI=1S/C9H13NO/c1-7(10)6-8-2-4-9(11)5-3-8/h2-5,7,11H,6,10H2,1H3
Chemical Name	4-(2-aminopropyl)phenol
HS Tariff Code	2934.99.9001
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)

Biological Activity

ADME/Pharmacokinetics	Absorption, Distribution and Excretion Intended for local use only (ophthalmic use). Intended for local use only (ophthalmic use). Intended for local use only (ophthalmic use). Intended for local use only (ophthalmic use). Metabolism / Metabolites Intended for local use only (ophthalmic use). 4-Hydroxyamphetamine is a known human metabolite of Amphetamine.
Toxicity/Toxicokinetics	Protein Binding Intended for local use only (ophthalmic use).
References	[1]. Mansoor Mughal, et al. Current pharmacologic testing for Horner syndrome. Curr Neurol Neurosci Rep. 2009 Sep;9(5):384-9.
Additional Infomation	4-(2-aminopropyl)phenol is a member of amphetamines. 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 is an Adrenergic Receptor Agonist. The mechanism of action of hydroxyamphetamine is as an Adrenergic Agonist. 4-(2-Aminopropyl)phenol has been reported in Senegalia berlandieri with data available. Hydroxyamphetamine is an indirect-acting sympathomimetic amine with adrenergic property. Hydroxyamphetamine, when applied topically to the eye, stimulates the release of norepinephrine from postganglionic adrenergic nerves resulting in the stimulation of both alpha and beta adrenergic receptors. Local alpha stimulatory effects include dilation of the pupil, increased flow of aqueous humor, and vasoconstriction; whereas beta stimulatory effects include relaxation of the ciliary muscle and a decreased production in aqueous humor. Amphetamine metabolite with sympathomimetic effects. It is sometimes called alpha-methyltyramine, which may also refer to the meta isomer, gepefrine. Drug Indication Mydriatic agent (eye pupil dilatation) for diagnosis of ophthalmic nerve lesions. Mechanism of Action Hydroxyamphetamine hydrobromide is an indirect acting sympathomimetic agent which causes the release of norepinephrine from adrenergic nerve terminals, resulting in mydriasis.

Solubility Data

Solubility (In Vitro)

DMSO: 100 mg/mL (661.33 mM)

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. 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. 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 corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

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.