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Details

Stereochemistry RACEMIC
Molecular Formula C9H13NO.BrH
Molecular Weight 232.118
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HYDROXYAMPHETAMINE HYDROBROMIDE

SMILES

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

InChI

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

HIDE SMILES / InChI

Molecular Formula BrH
Molecular Weight 80.912
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
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
A study of the metabolism of methamphetamine and 4-bromo-2,5-dimethoxyphenethylamine (2C-B) in isolated rat hepatocytes.
2005 Mar 10
Cation-selective exhaustive injection and sweeping MEKC for direct analysis of methamphetamine and its metabolites in urine.
2006 Dec
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
p-Hydroxyamphetamine causes prepulse inhibition disruptions in mice: contribution of dopamine neurotransmission.
2010 Dec 25
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 Fri Dec 15 18:57:14 UTC 2023
Edited
by admin
on Fri Dec 15 18:57:14 UTC 2023
Record UNII
59IG47SZ0E
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
HYDROXYAMPHETAMINE HYDROBROMIDE
MI   ORANGE BOOK   USP   USP-RS   VANDF  
Systematic Name English
HYDROXYAMFETAMINE HBR
Common Name English
PHENOL, 4-(2-AMINOPROPYL)-, HYDROBROMIDE
Systematic Name English
(±)-P-(2-AMINOPROPYL)PHENOL HBR
Common Name English
HYDROXYAMPHETAMINE HYDROBROMIDE [USP-RS]
Common Name English
HYDROXYAMPHETAMINE HYDROBROMIDE COMPONENT OF PAREMYD
Common Name English
HYDROXYAMFETAMINE HYDROBROMIDE
MART.   WHO-DD  
Common Name English
PAREMYD COMPONENT HYDROXYAMPHETAMINE HYDROBROMIDE
Common Name English
HYDROXYAMPHETAMINE HYDROBROMIDE [VANDF]
Common Name English
PAREDRINE
Common Name English
HYDROXYAMFETAMINE HYDROBROMIDE [MART.]
Common Name English
(±)-P-(2-AMINOPROPYL)PHENOL HYDROBROMIDE
Common Name English
HYDROXYAMPHETAMINE HBR
Common Name English
NSC-61065
Code English
HYDROXYAMPHETAMINE HYDROBROMIDE [ORANGE BOOK]
Common Name English
HYDROXYAMPHETAMINE HYDROBROMIDE [MI]
Common Name English
Hydroxyamfetamine hydrobromide [WHO-DD]
Common Name English
HYDROXYAMPHETAMINE HYDROBROMIDE [USP MONOGRAPH]
Common Name English
PHENOL, 4-(2-AMINOPROPYL)-, HBR
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29747
Created by admin on Fri Dec 15 18:57:14 UTC 2023 , Edited by admin on Fri Dec 15 18:57:14 UTC 2023
Code System Code Type Description
ECHA (EC/EINECS)
206-181-4
Created by admin on Fri Dec 15 18:57:14 UTC 2023 , Edited by admin on Fri Dec 15 18:57:14 UTC 2023
PRIMARY
MERCK INDEX
m6117
Created by admin on Fri Dec 15 18:57:14 UTC 2023 , Edited by admin on Fri Dec 15 18:57:14 UTC 2023
PRIMARY Merck Index
FDA UNII
59IG47SZ0E
Created by admin on Fri Dec 15 18:57:14 UTC 2023 , Edited by admin on Fri Dec 15 18:57:14 UTC 2023
PRIMARY
ChEMBL
CHEMBL1546
Created by admin on Fri Dec 15 18:57:14 UTC 2023 , Edited by admin on Fri Dec 15 18:57:14 UTC 2023
PRIMARY
SMS_ID
100000086712
Created by admin on Fri Dec 15 18:57:14 UTC 2023 , Edited by admin on Fri Dec 15 18:57:14 UTC 2023
PRIMARY
EVMPD
SUB02581MIG
Created by admin on Fri Dec 15 18:57:14 UTC 2023 , Edited by admin on Fri Dec 15 18:57:14 UTC 2023
PRIMARY
EPA CompTox
DTXSID0045961
Created by admin on Fri Dec 15 18:57:14 UTC 2023 , Edited by admin on Fri Dec 15 18:57:14 UTC 2023
PRIMARY
DAILYMED
59IG47SZ0E
Created by admin on Fri Dec 15 18:57:14 UTC 2023 , Edited by admin on Fri Dec 15 18:57:14 UTC 2023
PRIMARY
NSC
61065
Created by admin on Fri Dec 15 18:57:14 UTC 2023 , Edited by admin on Fri Dec 15 18:57:14 UTC 2023
PRIMARY
RS_ITEM_NUM
1325005
Created by admin on Fri Dec 15 18:57:14 UTC 2023 , Edited by admin on Fri Dec 15 18:57:14 UTC 2023
PRIMARY
NCI_THESAURUS
C47558
Created by admin on Fri Dec 15 18:57:14 UTC 2023 , Edited by admin on Fri Dec 15 18:57:14 UTC 2023
PRIMARY
RXCUI
82066
Created by admin on Fri Dec 15 18:57:14 UTC 2023 , Edited by admin on Fri Dec 15 18:57:14 UTC 2023
PRIMARY RxNorm
DRUG BANK
DBSALT001968
Created by admin on Fri Dec 15 18:57:14 UTC 2023 , Edited by admin on Fri Dec 15 18:57:14 UTC 2023
PRIMARY
PUBCHEM
9377
Created by admin on Fri Dec 15 18:57:14 UTC 2023 , Edited by admin on Fri Dec 15 18:57:14 UTC 2023
PRIMARY
CAS
306-21-8
Created by admin on Fri Dec 15 18:57:14 UTC 2023 , Edited by admin on Fri Dec 15 18:57:14 UTC 2023
PRIMARY
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