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
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
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).
Approval Year
Cmax
| 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 |
T1/2
| 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 |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes | yes (co-administration study) Comment: Coadministration of quinidine (CYP2D6 inhibitor) increased methoxyphenamine excretion in 32-h urine by 103%. |
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 |
|
| LC-MS method for the determination of albuterol enantiomers in human plasma using manual solid-phase extraction and a non-deuterated internal standard. | 2003 Apr 10 |
|
| Analysis of benzene ethylamine derivatives in urine using the programmable dynamic liquid-phase microextraction (LPME) device. | 2003 Dec |
|
| Anti-inflammatory effect of methoxyphenamine compound in rat model of chronic obstructive pulmonary disease. | 2003 Dec |
|
| HPLC determination of aminophylline, methoxyphenamine hydrochloride, noscapine and chlorphenamine maleate in compound dosage forms with an aqueous-organic mobile phase. | 2003 Sep 15 |
|
| Analysis of ethambutol and methoxyphenamine by capillary electrophoresis with electrochemiluminescence detection. | 2006 Jul 28 |
|
| Microchip-based liquid-liquid extraction for gas-chromatography analysis of amphetamine-type stimulants in urine. | 2006 Sep 29 |
|
| Doping control analysis of methoxyphenamine using liquid chromatography-tandem mass spectrometry. | 2008 |
|
| Induction of metamorphosis of pediveliger larvae of the mussel Mytilus galloprovincialis Lamarck, 1819 using neuroactive compounds, KCl, NH4Cl and organic solvents. | 2008 |
|
| 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 |
|
| 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 |
|
| Simultaneous determination of eight sympathomimetic amines in urine by gas chromatography/mass spectrometry. | 2010 Jan-Feb |
|
| Efficacy and safety of modified sequential three-step empirical therapy for chronic cough. | 2010 Jul |
|
| Stimulants and doping in sport. | 2010 Mar |
Patents
Sample Use Guides
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).
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NCI_THESAURUS |
C48149
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WHO-ATC |
R03CB02
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WHO-VATC |
QR03CB02
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DB13624
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SUB08860MIG
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100000081437
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CHEMBL2010507
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29704
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J3Z5SRI26Z
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1755
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93-30-1
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C005157
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DTXSID0023292
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Methoxyphenamine
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4117
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137
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m7341
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134817
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C83958
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202-237-7
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ACTIVE MOIETY
METABOLITE (PARENT)
SALT/SOLVATE (PARENT)
