Hydroxyamphetamine

Identification

Summary

Hydroxyamphetamine is an indirectly acting sympathomimetic agent producing mydriasis for diagnostic purposes.

Brand Names

Paremyd

Generic Name

Hydroxyamphetamine

DrugBank Accession Number

DB09352

Background

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.

Type

Small Molecule

Groups

Approved

Structure

Similar Structures

Weight: Average: 151.2056
Monoisotopic: 151.099714043
Chemical Formula: C₉H₁₃NO

Synonyms

4-(2-aminopropyl)phenol
4-hydroxyamphetamine
dl-4-hydroxyamphetamine
dl-p-hydroxyamphetamine
Hydroxyamphetamine
p-hydroxyamphetamine

External IDs

NSC-170995

Pharmacology

Indication

Mydriatic agent (eye pupil dilatation) for diagnosis of ophthalmic nerve lesions.

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Associated Therapies

Induction of Mydriasis

Contraindications & Blackbox Warnings

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Pharmacodynamics

Not Available

Mechanism of action

Hydroxyamphetamine hydrobromide is an indirect acting sympathomimetic agent which causes the release of norepinephrine from adrenergic nerve terminals, resulting in mydriasis.

Absorption

Intended for local use only (ophthalmic use).

Volume of distribution

Intended for local use only (ophthalmic use).

Protein binding

Intended for local use only (ophthalmic use).

Metabolism

Intended for local use only (ophthalmic use).

Route of elimination

Intended for local use only (ophthalmic use).

Half-life

Not Available

Clearance

Intended for local use only (ophthalmic use).

Adverse Effects

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Toxicity

No data available.

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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Acetazolamide	Acetazolamide may decrease the excretion rate of Hydroxyamphetamine which could result in a higher serum level.
Aminophylline	The risk or severity of adverse effects can be increased when Hydroxyamphetamine is combined with Aminophylline.
Bromotheophylline	The risk or severity of adverse effects can be increased when Hydroxyamphetamine is combined with Bromotheophylline.
Caffeine	The risk or severity of adverse effects can be increased when Hydroxyamphetamine is combined with Caffeine.
Dyphylline	The risk or severity of adverse effects can be increased when Hydroxyamphetamine is combined with Dyphylline.
Escitalopram	The risk or severity of serotonin syndrome can be increased when Hydroxyamphetamine is combined with Escitalopram.
Fenfluramine	The risk or severity of serotonin syndrome can be increased when Hydroxyamphetamine is combined with Fenfluramine.
Fluoxetine	The risk or severity of serotonin syndrome can be increased when Hydroxyamphetamine is combined with Fluoxetine.
Formoterol	Hydroxyamphetamine may increase the sympathomimetic activities of Formoterol.
Glyburide	The therapeutic efficacy of Glyburide can be decreased when used in combination with Hydroxyamphetamine.

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Food Interactions

No interactions found.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Hydroxyamfetamine hydrobromide	59IG47SZ0E	306-21-8	RZCJLMTXBMNRAD-UHFFFAOYSA-N

International/Other Brands

Norveritol / Pulsoton

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Paremyd	Hydroxyamfetamine hydrobromide (10 mg/1mL) + Tropicamide (2.5 mg/1mL)	Solution	Ophthalmic	Akorn	1992-01-30	Not applicable

Categories

Drug Categories

Chemical TaxonomyProvided by Classyfire

Description: This compound belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
Kingdom: Organic compounds
Super Class: Benzenoids
Class: Benzene and substituted derivatives
Sub Class: Phenethylamines
Direct Parent: Amphetamines and derivatives
Alternative Parents: Phenylpropanes / Aralkylamines / 1-hydroxy-2-unsubstituted benzenoids / Organopnictogen compounds / Organooxygen compounds / Monoalkylamines / Hydrocarbon derivatives
Substituents: 1-hydroxy-2-unsubstituted benzenoid / Amine / Amphetamine or derivatives / Aralkylamine / Aromatic homomonocyclic compound / Hydrocarbon derivative / Organic nitrogen compound / Organic oxygen compound / Organonitrogen compound / Organooxygen compound
Molecular Framework: Aromatic homomonocyclic compounds
External Descriptors: Not Available

Affected organisms

Not Available

Chemical Identifiers

UNII: FQR280JW2N
CAS number: 103-86-6
InChI Key: GIKNHHRFLCDOEU-UHFFFAOYSA-N
InChI: InChI=1S/C9H13NO/c1-7(10)6-8-2-4-9(11)5-3-8/h2-5,7,11H,6,10H2,1H3
IUPAC Name: 4-(2-aminopropyl)phenol
SMILES: CC(N)CC1=CC=C(O)C=C1

References

General References

product info [Link]
American Academy of Ophthalmology - Horner syndrome Article [Link]
product info [Link]

External Links

Human Metabolome Database: HMDB0060765
PubChem Compound: 3651
PubChem Substance: 347827833
ChemSpider: 3525
BindingDB: 81459
RxNav: 7839
ChEBI: 103855
ChEMBL: CHEMBL1546
Wikipedia: 4-Hydroxyamphetamine

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Solution	Ophthalmic

Prices

Not Available

Patents

Not Available

Properties

State

Not Available

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	3.13 mg/mL	ALOGPS
logP	0.58	ALOGPS
logP	1	Chemaxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	10.48	Chemaxon
pKa (Strongest Basic)	9.8	Chemaxon
Physiological Charge	1	Chemaxon
Hydrogen Acceptor Count	2	Chemaxon
Hydrogen Donor Count	2	Chemaxon
Polar Surface Area	46.25 Å²	Chemaxon
Rotatable Bond Count	2	Chemaxon
Refractivity	45.69 m³·mol^-1	Chemaxon
Polarizability	17.17 Å³	Chemaxon
Number of Rings	1	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available

Drug created at November 30, 2015 19:10 / Updated at June 12, 2020 16:52