NAV

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
3D
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
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Pharmacology

Indication

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

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Associated Therapies
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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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.
DrugInteraction
Integrate drug-drug
interactions in your software
AcetazolamideAcetazolamide may decrease the excretion rate of Hydroxyamphetamine which could result in a higher serum level.
AminophyllineThe risk or severity of adverse effects can be increased when Hydroxyamphetamine is combined with Aminophylline.
BromotheophyllineThe risk or severity of adverse effects can be increased when Hydroxyamphetamine is combined with Bromotheophylline.
CaffeineThe risk or severity of adverse effects can be increased when Hydroxyamphetamine is combined with Caffeine.
DesvenlafaxineThe risk or severity of serotonin syndrome can be increased when Desvenlafaxine is combined with Hydroxyamphetamine.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Hydroxyamfetamine hydrobromide59IG47SZ0E306-21-8RZCJLMTXBMNRAD-UHFFFAOYSA-N
International/Other Brands
Norveritol / Pulsoton
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ParemydHydroxyamfetamine hydrobromide (10 mg/1mL) + Tropicamide (2.5 mg/1mL)SolutionOphthalmicAkorn1992-01-30Not applicableUS flag

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
  1. product info [Link]
  2. American Academy of Ophthalmology - Horner syndrome Article [Link]
  3. product info [Link]
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 Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SolutionOphthalmic
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility3.13 mg/mLALOGPS
logP0.58ALOGPS
logP1Chemaxon
logS-1.7ALOGPS
pKa (Strongest Acidic)10.48Chemaxon
pKa (Strongest Basic)9.8Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area46.25 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity45.69 m3·mol-1Chemaxon
Polarizability17.17 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0006-9800000000-be314d40e4f3eec02c64
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-052r-0900000000-e3e7c5dc80df1c7ac90c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0900000000-68772c2bed59cefd1a45
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-066u-5900000000-09d4c77b933b78183b8e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0f8c-2900000000-2f04ef91938530175f31
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-9200000000-eab84f6953169900c916
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9100000000-7cd0bf5f869003f34b82
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-052r-0900000000-e3e7c5dc80df1c7ac90c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0900000000-68772c2bed59cefd1a45
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-066u-5900000000-09d4c77b933b78183b8e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0f8c-2900000000-2f04ef91938530175f31
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-9200000000-eab84f6953169900c916
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9100000000-7cd0bf5f869003f34b82
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-136.8650887
predicted
DarkChem Lite v0.1.0
[M-H]-133.74898
predicted
DeepCCS 1.0 (2019)
[M-H]-136.8650887
predicted
DarkChem Lite v0.1.0
[M-H]-133.74898
predicted
DeepCCS 1.0 (2019)
[M+H]+137.9569887
predicted
DarkChem Lite v0.1.0
[M+H]+137.47163
predicted
DeepCCS 1.0 (2019)
[M+H]+137.9569887
predicted
DarkChem Lite v0.1.0
[M+H]+137.47163
predicted
DeepCCS 1.0 (2019)
[M+Na]+136.6392887
predicted
DarkChem Lite v0.1.0
[M+Na]+146.94884
predicted
DeepCCS 1.0 (2019)
[M+Na]+136.6392887
predicted
DarkChem Lite v0.1.0
[M+Na]+146.94884
predicted
DeepCCS 1.0 (2019)

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