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Details

Stereochemistry RACEMIC
Molecular Formula C9H13NO
Molecular Weight 151.2056
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HYDROXYAMPHETAMINE

SMILES

CC(N)CC1=CC=C(O)C=C1

InChI

InChIKey=GIKNHHRFLCDOEU-UHFFFAOYSA-N
InChI=1S/C9H13NO/c1-7(10)6-8-2-4-9(11)5-3-8/h2-5,7,11H,6,10H2,1H3

HIDE SMILES / InChI

Molecular Formula C9H13NO
Molecular Weight 151.2056
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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 hydrobromide is a component of FDA approved brand drug - Paremyd sterile ophthalmic solution (Hydroxyamphetamine hydrobromide, USP 1.0%, Tropicamide, USP 0.25%). Hydroxyamphetamine is an indirect-acting sympathomimetic, while tropicamide acts as a parasympatholytic.

CNS Activity

Curator's Comment: The blood-brain barrier is permutle to Hydroxyamphetamine in rats. Hydroxyamphetamine is CNS active

Originator

Curator's Comment: Abbot and Henry introduced the use of paredrine (hydroxyamphetamine).

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Paremyd

Approved Use

PAREMYD Solution is indicated for mydriasis in routine diagnostic procedures and in conditions where short-term pupil dilation is desired. PAREMYD provides clinically significant mydriasis with partial cycloplegia.

Launch Date

6.967296E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.8 μg/mL
10 mg/kg bw single, intravenous
dose: 10 mg/kg bw
route of administration: Intravenous
experiment type: SINGLE
co-administered:
HYDROXYAMPHETAMINE plasma
Canis lupus
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
4 μg × h/mL
10 mg/kg bw single, intravenous
dose: 10 mg/kg bw
route of administration: Intravenous
experiment type: SINGLE
co-administered:
HYDROXYAMPHETAMINE plasma
Canis lupus
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3 h
10 mg/kg bw single, intravenous
dose: 10 mg/kg bw
route of administration: Intravenous
experiment type: SINGLE
co-administered:
HYDROXYAMPHETAMINE plasma
Canis lupus
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
PubMed

PubMed

TitleDatePubMed
Hydroxyamphetamine drops for Horner's syndrome.
2001 Aug
Determination of amphetamine and its metabolite p-hydroxyamphetamine in rat urine by reversed-phase high-performance liquid chromatography after dabsyl derivatization.
2001 Nov
Horner syndrome.
2003 Dec
Screening for and validated quantification of amphetamines and of amphetamine- and piperazine-derived designer drugs in human blood plasma by gas chromatography/mass spectrometry.
2003 Jun
False negative hydroxyamphetamine test in horner syndrome caused by acute internal carotid artery dissection.
2003 Mar
The correlation of phenylephrine 1% with hydroxyamphetamine 1% in Horner's syndrome.
2004 Apr
Monoamine oxidase and head-twitch response in mice. Mechanisms of alpha-methylated substrate derivatives.
2004 Jan
Simultaneous determination of amphetamine derivatives in human urine after SPE extraction and HPLC-UV analysis.
2004 Mar
A study of the metabolism of methamphetamine and 4-bromo-2,5-dimethoxyphenethylamine (2C-B) in isolated rat hepatocytes.
2005 Mar 10
Trace amine-associated receptor 1 displays species-dependent stereoselectivity for isomers of methamphetamine, amphetamine, and para-hydroxyamphetamine.
2007 Apr
Determination of amphetamine, methamphetamine, and hydroxyamphetamine derivatives in urine by gas chromatography-mass spectrometry and its relation to CYP2D6 phenotype of drug users.
2007 Jan-Feb
Novel biomarkers of prenatal methamphetamine exposure in human meconium.
2009 Feb
Current pharmacologic testing for Horner syndrome.
2009 Sep
Central administration of p-hydroxyamphetamine produces a behavioral stimulant effect in rodents: evidence for the involvement of dopaminergic systems.
2010 Feb
Patents

Sample Use Guides

Mydriasis: Ophthalmic: Instill 1 to 2 drops into conjunctival sac(s)
Route of Administration: Topical
SH-SY5Y neurons were incubated with Hydroxyamphetamine (concentration range 0-10mM) for 24 or 48h, and the viability was determined by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) and lactate dehydrogenase (LDH) leakage assays.. For Hydroxyamphetamine the TC50 was not reached in the tested concentration range. Hydroxyamphetamine at 8.00mM originated few late apoptotic cells
Substance Class Chemical
Created
by admin
on Thu Jul 06 02:06:02 UTC 2023
Edited
by admin
on Thu Jul 06 02:06:02 UTC 2023
Record UNII
FQR280JW2N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
HYDROXYAMPHETAMINE
MI   VANDF  
Systematic Name English
4-(2-AMINOPROPYL)PHENOL
Systematic Name English
NORVERITOL
Brand Name English
hydroxyamfetamine [INN]
Common Name English
P-HYDROXYAMPHETAMINE
Common Name English
4-HYDROXYAMPHETAMINE
Systematic Name English
DL-4-HYDROXYAMPHETAMINE
Common Name English
PULSOTON
Brand Name English
PHENOL, P-(2-AMINOPROPYL)-
Common Name English
HYDROXYAMPHETAMINE [MI]
Common Name English
DL-P-HYDROXYAMPHETAMINE
Common Name English
Hydroxyamfetamine [WHO-DD]
Common Name English
(±)-P-(2-AMINOPROPYL)PHENOL
Common Name English
HYDROXYAMPHETAMINE [VANDF]
Common Name English
RACEMIC P-HYDROXYAMPHETAMINE
Common Name English
NSC-170995
Code English
4-HYDROXY-.ALPHA.-METHYLPHENETHYLAMINE
Systematic Name English
OH-A
Common Name English
HYDROXYAMFETAMINE
INN   WHO-DD  
INN  
Official Name English
PHENOL, 4-(2-AMINOPROPYL)-
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C29747
Created by admin on Thu Jul 06 02:06:02 UTC 2023 , Edited by admin on Thu Jul 06 02:06:02 UTC 2023
NDF-RT N0000000122
Created by admin on Thu Jul 06 02:06:02 UTC 2023 , Edited by admin on Thu Jul 06 02:06:02 UTC 2023
NDF-RT N0000175883
Created by admin on Thu Jul 06 02:06:02 UTC 2023 , Edited by admin on Thu Jul 06 02:06:02 UTC 2023
Code System Code Type Description
WIKIPEDIA
4-Hydroxyamphetamine
Created by admin on Thu Jul 06 02:06:02 UTC 2023 , Edited by admin on Thu Jul 06 02:06:02 UTC 2023
PRIMARY
DRUG BANK
DB09352
Created by admin on Thu Jul 06 02:06:02 UTC 2023 , Edited by admin on Thu Jul 06 02:06:02 UTC 2023
PRIMARY
INN
136
Created by admin on Thu Jul 06 02:06:02 UTC 2023 , Edited by admin on Thu Jul 06 02:06:02 UTC 2023
PRIMARY
EPA CompTox
DTXSID3023134
Created by admin on Thu Jul 06 02:06:02 UTC 2023 , Edited by admin on Thu Jul 06 02:06:02 UTC 2023
PRIMARY
SMS_ID
100000084199
Created by admin on Thu Jul 06 02:06:02 UTC 2023 , Edited by admin on Thu Jul 06 02:06:02 UTC 2023
PRIMARY
CAS
103-86-6
Created by admin on Thu Jul 06 02:06:02 UTC 2023 , Edited by admin on Thu Jul 06 02:06:02 UTC 2023
PRIMARY
ECHA (EC/EINECS)
203-152-8
Created by admin on Thu Jul 06 02:06:02 UTC 2023 , Edited by admin on Thu Jul 06 02:06:02 UTC 2023
PRIMARY
NCI_THESAURUS
C61787
Created by admin on Thu Jul 06 02:06:02 UTC 2023 , Edited by admin on Thu Jul 06 02:06:02 UTC 2023
PRIMARY
DRUG CENTRAL
1394
Created by admin on Thu Jul 06 02:06:02 UTC 2023 , Edited by admin on Thu Jul 06 02:06:02 UTC 2023
PRIMARY
PUBCHEM
3651
Created by admin on Thu Jul 06 02:06:02 UTC 2023 , Edited by admin on Thu Jul 06 02:06:02 UTC 2023
PRIMARY
EVMPD
SUB08075MIG
Created by admin on Thu Jul 06 02:06:02 UTC 2023 , Edited by admin on Thu Jul 06 02:06:02 UTC 2023
PRIMARY
MESH
D010136
Created by admin on Thu Jul 06 02:06:02 UTC 2023 , Edited by admin on Thu Jul 06 02:06:02 UTC 2023
PRIMARY
ChEMBL
CHEMBL1546
Created by admin on Thu Jul 06 02:06:02 UTC 2023 , Edited by admin on Thu Jul 06 02:06:02 UTC 2023
PRIMARY
MERCK INDEX
M6117
Created by admin on Thu Jul 06 02:06:02 UTC 2023 , Edited by admin on Thu Jul 06 02:06:02 UTC 2023
PRIMARY Merck Index
NSC
170995
Created by admin on Thu Jul 06 02:06:02 UTC 2023 , Edited by admin on Thu Jul 06 02:06:02 UTC 2023
PRIMARY
RXCUI
7839
Created by admin on Thu Jul 06 02:06:02 UTC 2023 , Edited by admin on Thu Jul 06 02:06:02 UTC 2023
PRIMARY RxNorm
FDA UNII
FQR280JW2N
Created by admin on Thu Jul 06 02:06:02 UTC 2023 , Edited by admin on Thu Jul 06 02:06:02 UTC 2023
PRIMARY
DAILYMED
FQR280JW2N
Created by admin on Thu Jul 06 02:06:02 UTC 2023 , Edited by admin on Thu Jul 06 02:06:02 UTC 2023
PRIMARY
CAS
1518-86-1
Created by admin on Thu Jul 06 02:06:02 UTC 2023 , Edited by admin on Thu Jul 06 02:06:02 UTC 2023
SUPERSEDED
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SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
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PARENT -> METABOLITE
MINOR
PARENT -> METABOLITE
PARENT -> METABOLITE ACTIVE
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ACTIVE MOIETY