HYDROXYAMPHETAMINE

US Previously Marketed

First marketed in 1935

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 Search

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	( + / - )

Description
Sources: https://www.drugbank.ca/drugs/DB09352 | https://www.drugs.com/cdi/hydroxyamphetamine-tropicamide.html | http://www.ophthalmologymanagement.com/issues/2002/december-2002/rx-perspective-unique-mydriatic-returns | http://www.akorn.com/documents/catalog/sell_sheets/17478-704-12.pdf

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adrenergic receptor 35 Target ID: CHEMBL2331074 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2825058 \| https://www.ncbi.nlm.nih.gov/pubmed/2990216 \| https://www.ncbi.nlm.nih.gov/pubmed/11176985 \| https://www.ncbi.nlm.nih.gov/pubmed/13884064	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Eye diseases 25 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/19261s8lbl.pdf https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=da8a8a19-ac1b-4160-aac4-c4c57598eb5d	Diagnostic		Approved 8429	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 1992

C_max

Value	Dose	Co-administered	Analyte	Population
1.8 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/13143480/	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

Value	Dose	Co-administered	Analyte	Population
4 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/13143480/	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/13143480/	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

Sourcing

Vendor/Aggregator	ID	URL
AA Blocks	AA00856U	http://www.aablocks.com/goods/Goods/detail?id=AA00856U
Alichem	19147718	http://www.alichem.com/en/products/103-86-6.html
Angene	AGN-PC-0JK6M7	http://www.angenechemical.com/productshow/AGN-PC-0JK6M7.html
AstaTech, Inc.	84990	http://www.astatechinc.com/CPSResult.php?CRNO=30730
Aurora Fine Chemicals LLC	A00.032.212	http://online.aurorafinechemicals.com/info?ID=A00.032.212
Aurora Fine Chemicals LLC	K04.662.171	http://online.aurorafinechemicals.com/info?ID=K04.662.171
Aurum Pharmatech LLC	NE22868	http://www.Aurumpharmatech.com/Product/ProductDetails/NE22868
Chem Scene	CS-4687	http://www.chemscene.com/103-86-6.html
Chemspace	CSSB00000185610	https://chem-space.com/CSSB00000185610
Enamine	Z57102382	https://www.enaminestore.com/catalog/Z57102382
Lab Network	LN01799481	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01799481
MedChem Express	HY-B1098	https://www.medchemexpress.com/Hydroxyamphetamine.html
MolPort	MolPort-004-316-667	https://www.molport.com/shop/molecule-link/MolPort-004-316-667
MuseChem	I000227	https://www.musechem.com/product/I000227.html
eNovation Chemicals	D335088	https://www.enovationchem.com/ProductDetails.asp?ProductID=D335088
mcule	MCULE-6999513658	https://mcule.com/MCULE-6999513658/

PubMed

Title	Date	PubMed
Hydroxyamphetamine drops for Horner's syndrome.	2001 Aug	11548139
Hydroxyamphetamine increases intraocular pressure in rabbits.	2001 Feb	11176985
Determination of amphetamine and its metabolite p-hydroxyamphetamine in rat urine by reversed-phase high-performance liquid chromatography after dabsyl derivatization.	2001 Nov	11746241
The contribution of the metabolite p-hydroxyamphetamine to the central actions of p-methoxyamphetamine.	2002 Mar	11875633
Horner syndrome.	2003 Dec	14615640
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	12827635
False negative hydroxyamphetamine test in horner syndrome caused by acute internal carotid artery dissection.	2003 Mar	12616084
The correlation of phenylephrine 1% with hydroxyamphetamine 1% in Horner's syndrome.	2004 Apr	15031194
Prolactinoma presenting as painful postganglionic Horner syndrome.	2004 Apr 27	15111696
Monoamine oxidase and head-twitch response in mice. Mechanisms of alpha-methylated substrate derivatives.	2004 Jan	14697897
Simultaneous determination of amphetamine derivatives in human urine after SPE extraction and HPLC-UV analysis.	2004 Mar	15039965
A study of the metabolism of methamphetamine and 4-bromo-2,5-dimethoxyphenethylamine (2C-B) in isolated rat hepatocytes.	2005 Mar 10	15639607
Cation-selective exhaustive injection and sweeping MEKC for direct analysis of methamphetamine and its metabolites in urine.	2006 Dec	17080473
Trace amine-associated receptor 1 displays species-dependent stereoselectivity for isomers of methamphetamine, amphetamine, and para-hydroxyamphetamine.	2007 Apr	17218486
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	17389081
Novel biomarkers of prenatal methamphetamine exposure in human meconium.	2009 Feb	19125148
Current pharmacologic testing for Horner syndrome.	2009 Sep	19664368
p-Hydroxyamphetamine causes prepulse inhibition disruptions in mice: contribution of dopamine neurotransmission.	2010 Dec 25	20540968
Central administration of p-hydroxyamphetamine produces a behavioral stimulant effect in rodents: evidence for the involvement of dopaminergic systems.	2010 Feb	19960188
New meconium biomarkers of prenatal methamphetamine exposure increase identification of affected neonates.	2010 May	20185623

Patents

Sample Use Guides

In Vivo Use Guide

Mydriasis: Ophthalmic: Instill 1 to 2 drops into conjunctival sac(s)

Route of Administration: Topical

In Vitro Use Guide

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 18:56:03 GMT 2023` Edited by `admin` on `Fri Dec 15 18:56:03 GMT 2023`
Record UNII	FQR280JW2N
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

HYDROXYAMPHETAMINE

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

Official Name

English

PHENOL, 4-(2-AMINOPROPYL)-

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29747