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=C(OC)C=CC=C1

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 87 Target ID: CHEMBL2094118 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6121608	Agonist 2678

Conditions

Condition	Modality	Highest Phase	Product
Asthma 241 Sources: https://prezi.com/n8kuaq5n38l2/methoxyphenamine/	Primary	Approved 8429	Unknown Approved Use Unknown
Chronic obstructive pulmonary disease 174 Sources: https://prezi.com/n8kuaq5n38l2/methoxyphenamine/	Primary	Approved 8429	Unknown Approved Use Unknown
Postinfectious cough 2 Sources: https://prezi.com/n8kuaq5n38l2/methoxyphenamine/	Primary	Approved 8429	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 1217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 1217	substrate 3367 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
Chromatographic analysis of phenethylamine-antihistamine combinations using C8, C18 or cyano columns and micellar sodium dodecyl sulfate-pentanol mixtures.	2001 Apr	11340978
Doping control analysis of methoxyphenamine using liquid chromatography-tandem mass spectrometry.	2008	18708694
Extraction of amphetamines and methylenedioxyamphetamines from urine using a monolithic silica disk-packed spin column and high-performance liquid chromatography-diode array detection.	2008 Oct 24	18790482
Generic sample preparation combined with high-resolution liquid chromatography-time-of-flight mass spectrometry for unification of urine screening in doping-control laboratories.	2010 Apr	20155493

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

O-METHOXY-N,.ALPHA.-DIMETHYLPHENETHYLAMINE

Common Name

English

METHOXYPHENAMINE [MI]

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