Hydroxyamphetamine

Identification

Name
Hydroxyamphetamine
Accession Number
DB09352
Type
Small Molecule
Groups
Approved
Description

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.

Structure
Thumb
Synonyms
  • 4-(2-aminopropyl)phenol
  • 4-hydroxyamphetamine
  • dl-4-hydroxyamphetamine
  • dl-p-hydroxyamphetamine
  • Hydroxyamphetamine
  • p-hydroxyamphetamine
External IDs
NSC-170995
Product Ingredients
IngredientUNIICASInChI Key
Hydroxyamfetamine hydrobromide59IG47SZ0E306-21-8RZCJLMTXBMNRAD-UHFFFAOYSA-N
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
ParemydHydroxyamfetamine hydrobromide (10 mg/1mL) + Tropicamide (2.5 mg/1mL)SolutionOphthalmicAkorn1992-01-30Not applicableUs
International/Other Brands
Norveritol / Pulsoton
Categories
UNII
FQR280JW2N
CAS number
103-86-6
Weight
Average: 151.2056
Monoisotopic: 151.099714043
Chemical Formula
C9H13NO
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

Pharmacology

Indication

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

Associated Therapies
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).

Toxicity

No data available.

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
3-isobutyl-1-methyl-7H-xanthineThe risk or severity of adverse effects can be increased when Hydroxyamphetamine is combined with 3-isobutyl-1-methyl-7H-xanthine.
6-O-benzylguanineThe risk or severity of adverse effects can be increased when Hydroxyamphetamine is combined with 6-O-benzylguanine.
7-DeazaguanineThe risk or severity of adverse effects can be increased when Hydroxyamphetamine is combined with 7-Deazaguanine.
7,9-DimethylguanineThe risk or severity of adverse effects can be increased when Hydroxyamphetamine is combined with 7,9-Dimethylguanine.
8-azaguanineThe risk or severity of adverse effects can be increased when Hydroxyamphetamine is combined with 8-azaguanine.
8-chlorotheophyllineThe risk or severity of adverse effects can be increased when Hydroxyamphetamine is combined with 8-chlorotheophylline.
9-DeazaguanineThe risk or severity of adverse effects can be increased when Hydroxyamphetamine is combined with 9-Deazaguanine.
9-MethylguanineThe risk or severity of adverse effects can be increased when Hydroxyamphetamine is combined with 9-Methylguanine.
AcefyllineThe risk or severity of adverse effects can be increased when Hydroxyamphetamine is combined with Acefylline.
BamifyllineThe risk or severity of adverse effects can be increased when Hydroxyamphetamine is combined with Bamifylline.
Food Interactions
Not Available

References

General References
  1. product info [Link]
  2. article [Link]
  3. product info [Link]
External Links
Human Metabolome Database
HMDB0060765
PubChem Compound
3651
PubChem Substance
347827833
ChemSpider
3525
BindingDB
81459
ChEBI
103855
ChEMBL
CHEMBL1546
Wikipedia
4-Hydroxyamphetamine

Clinical Trials

Clinical Trials
Not Available

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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Amphetamine or derivatives / Phenylpropane / 1-hydroxy-2-unsubstituted benzenoid / Aralkylamine / Phenol / Organic nitrogen compound / Organic oxygen compound / Organopnictogen compound / Hydrocarbon derivative / Primary amine
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Drug created on November 30, 2015 12:10 / Updated on November 02, 2018 09:00