METHOXYPHENAMINE

US Previously Marketed

First approved in 1949

Details

Stereochemistry	RACEMIC
Molecular Formula	C11H17NO
Molecular Weight	179.2588
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CNC(C)CC1=CC=CC=C1OC

InChI

InChIKey=OEHAYUOVELTAPG-UHFFFAOYSA-N

InChI=1S/C11H17NO/c1-9(12-2)8-10-6-4-5-7-11(10)13-3/h4-7,9,12H,8H2,1-3H3

HIDE SMILES / InChI

Description
Sources: https://prezi.com/n8kuaq5n38l2/methoxyphenamine/ https://www.ncbi.nlm.nih.gov/pubmed/18708694

Methoxyphenamine also known as 2-methoxy-N-methylamphetamine (OMMA), is a beta adrenergic receptor agonist nd is used as a bronchodilator to treat asthma, chronic obstructive pulmonary disease (COPD) and postinfectious cough. In addition, methoxyphenamine using is prohibited in sports according to the regulations of the World Anti-Doping Agency (WADA).

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adrenergic receptor beta 89 Target ID: CHEMBL2094118 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6121608	Agonist 2752

Conditions

Condition	Modality	Highest Phase	Product
Asthma 244 Sources: https://prezi.com/n8kuaq5n38l2/methoxyphenamine/	Primary	Approved 8583	Unknown Approved Use Unknown
Chronic obstructive pulmonary disease 175 Sources: https://prezi.com/n8kuaq5n38l2/methoxyphenamine/	Primary	Approved 8583	Unknown Approved Use Unknown
Postinfectious cough 2 Sources: https://prezi.com/n8kuaq5n38l2/methoxyphenamine/	Primary	Approved 8583	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
157 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3625484	60.3 mg single, oral dose: 60.3 mg route of administration: Oral experiment type: SINGLE co-administered:		METHOXYPHENAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
1315 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3625484	60.3 mg single, oral dose: 60.3 mg route of administration: Oral experiment type: SINGLE co-administered:		METHOXYPHENAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3625484	60.3 mg single, oral dose: 60.3 mg route of administration: Oral experiment type: SINGLE co-administered:		METHOXYPHENAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
		substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 1388	substrate 4014 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=000093301, https://pubmed.ncbi.nlm.nih.gov/8553683/, https://pubmed.ncbi.nlm.nih.gov/1761076/	yes		yes (co-administration study) Comment: Coadministration of quinidine (CYP2D6 inhibitor) increased methoxyphenamine excretion in 32-h urine by 103%. Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=000093301, https://pubmed.ncbi.nlm.nih.gov/8553683/, https://pubmed.ncbi.nlm.nih.gov/1761076/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:134817	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:134817
ChemicalBook	CB2512394	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB2512394
eMolecules	1012267	https://www.emolecules.com/cgi-bin/more?vid=1012267

PubMed

Title	Date	PubMed
Efficacy and safety of modified sequential three-step empirical therapy for chronic cough.	2010-07	20546197
Generic sample preparation combined with high-resolution liquid chromatography-time-of-flight mass spectrometry for unification of urine screening in doping-control laboratories.	2010-04	20155493
Simultaneous determination of eight sympathomimetic amines in urine by gas chromatography/mass spectrometry.	2010-03-26	20334173
Stimulants and doping in sport.	2010-03	20122452
Extraction of amphetamines and methylenedioxyamphetamines from urine using a monolithic silica disk-packed spin column and high-performance liquid chromatography-diode array detection.	2008-10-24	18790482
Doping control analysis of methoxyphenamine using liquid chromatography-tandem mass spectrometry.	2008	18708694
Induction of metamorphosis of pediveliger larvae of the mussel Mytilus galloprovincialis Lamarck, 1819 using neuroactive compounds, KCl, NH4Cl and organic solvents.	2008	18701989
Microchip-based liquid-liquid extraction for gas-chromatography analysis of amphetamine-type stimulants in urine.	2006-09-29	16872620
Analysis of ethambutol and methoxyphenamine by capillary electrophoresis with electrochemiluminescence detection.	2006-07-28	16797572
Analysis of benzene ethylamine derivatives in urine using the programmable dynamic liquid-phase microextraction (LPME) device.	2003-12	14737229
Anti-inflammatory effect of methoxyphenamine compound in rat model of chronic obstructive pulmonary disease.	2003-12	14653967
HPLC determination of aminophylline, methoxyphenamine hydrochloride, noscapine and chlorphenamine maleate in compound dosage forms with an aqueous-organic mobile phase.	2003-09-15	12946529
LC-MS method for the determination of albuterol enantiomers in human plasma using manual solid-phase extraction and a non-deuterated internal standard.	2003-04-10	12667940
Chromatographic analysis of phenethylamine-antihistamine combinations using C8, C18 or cyano columns and micellar sodium dodecyl sulfate-pentanol mixtures.	2001-04	11340978

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Oral

In Vitro Use Guide

It was revealed, that methoxyphenamine antagonizes the effects of histamine both in vivo and in vitro. In vitro studies indicate a noncompetitive antagonism. Histamine-induced contractions of the isolated guinea-pig ileum were antagonized by methoxyphenamine (10(-5) to 10(-3) M). The histamine log-concentration-response curve was shifted to the right in a parallel manner by methoxyphenamine (10(-5) to 10(-4) M), without depression of maximum responses. However, at higher concentrations, maximum responses were reduced. The slope of the Schild plot was significantly different from -1. The degree of the rightward shift of the concentration-response curves to histamine, produced by 10(-5) M of methoxyphenamine [3.90-(2.83, 4.97) fold], was not significantly different from that produced by 3 x 10(-9) M of mepyramine [4.60-(2.86, 6.52) fold]. Methoxyphenamine, at concentrations of 10(-5) to 3 x 10(-4) M, had no significant effect on responses of guinea-pig ilea to acetylcholine (10(-9) to 10(-5) M).

Name

Type

Language

METHOXYPHENAMINE

Official Name

English

METHOXYPHENAMINE [MI]

Preferred Name

English

O-METHOXY-N,.ALPHA.-DIMETHYLPHENETHYLAMINE

Common Name

English

Methoxyphenamine [WHO-DD]

Common Name

English

BENZENEETHANAMINE, 2-METHOXY-N,.ALPHA.-DIMETHYL-

Systematic Name

English

methoxyphenamine [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C48149