Page last updated: 2024-12-05

methoxyphenamine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Methoxyphenamine is an antihistamine that was once used to treat allergies. It is a derivative of pheniramine and has a similar chemical structure. Methoxyphenamine acts as an antagonist of histamine receptors, preventing histamine from binding to these receptors and causing allergic reactions. However, methoxyphenamine has been largely replaced by newer, safer antihistamines. It is no longer widely available in the United States and other countries. It is sometimes studied for its potential use in treating other conditions, such as Parkinson's disease, but it is not currently approved for these uses.'

methoxyphenamine: structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

methoxyphenamine : An amphetamine methylated on nitrogen and with the phenyl ring methoxylated at C-2. A beta-adrenergic receptor agonist, it is used as a bronchodilator. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID4117
CHEMBL ID2010507
CHEBI ID134817
SCHEMBL ID218289
MeSH IDM0046501

Synonyms (76)

Synonym
AC-16015
benzeneethanamine, 2-methoxy-n,.alpha.-dimethyl-
phenethylamine, o-methoxy-n,.alpha.-dimethyl-
NCI60_019552
methoxyphenamine
93-30-1
n-methyl-1-[2-(methyloxy)phenyl]propan-2-amine
NCGC00159469-02
NCGC00159469-03
methoxiphenadrinum
2-methoxy-n,alpha-dimethylphenethylamin
phenethylamine, 2-methoxy-n,alpha-dimethyl-
oxalacetic acid orthoxine
2-methoxy-n,alpha-dimethylphenethylamine
o-methoxy-n,alpha-dimethylphenethylamine
metossifenamina [dcit]
euspirol
metoxifenaminio [inn-spanish]
methoxyphenamine [inn:ban]
methoxyphenaminum [inn-latin]
methoxifenaminio
orthoxine
einecs 202-237-7
proasma
methoxyphenaminum
omma
1-(2-methoxyphenyl)-n-methylpropan-2-amine
methoxyphenamin
methoxiphenadrin
metoxifenamina
CHEBI:134817
2-methoxymethamphetamine
ortodrinex
j3z5sri26z ,
metossifenamina
unii-j3z5sri26z
metoxifenaminio
benzeneethanamine, 2-methoxy-n,alpha-dimethyl-
dtxsid0023292 ,
cas-93-30-1
tox21_113045
dtxcid203292
AKOS009939590
methoxyphenamine [who-dd]
methoxyphenamine [mi]
o-methoxy-n,.alpha.-dimethylphenethylamine
methoxyphenamine [inn]
CHEMBL2010507
SCHEMBL218289
NCGC00159469-04
tox21_113045_1
OEHAYUOVELTAPG-UHFFFAOYSA-N
2-methoxy-n-methylamphetamine
2-methoxy-n,.alpha.-dimethylphenethylamine
.beta.-(o-methoxyphenyl)isopropylmethylamine
ortoxine
methamphetamine, 2-methoxy
1-(o-methoxyphenyl)-2-methylaminopropane
.alpha.-(2-methoxyphenyl)-.beta.-methylaminopropane
2-methoxy-n,.alpha.-dimethylbenzeneethanamine
methoxyphenadrine
[1-(2-methoxyphenyl)propan-2-yl](methyl)amine
1-(2-methoxyphenyl)-n-methyl-2-propanamine
SR-01000944496-1
sr-01000944496
2-methoxy-n,alpha-dimethyl-benzeneethanamine
o-methoxy-n,alpha-dimethyl-phenethylamine
beta-(o-methoxyphenyl)isopropylmethylamine
2-methoxy-n,alpha-dimethylbenzeneethanamine
alpha-(2-methoxyphenyl)-beta-methylaminopropane
2-methoxyphenamine hcl
DB13624
Q6823901
N10866
bdbm50595336
EN300-92107

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Secondary end-points were the rate of control of chronic cough at each step of therapy, the duration of treatment required, changes in cough symptom score, health-related quality of life and possible adverse effects."( Efficacy and safety of modified sequential three-step empirical therapy for chronic cough.
Li, X; Liang, S; Liu, B; Lü, H; Qiu, Z; Wang, L; Wang, Y; Wei, W; Yu, L, 2010
)
0.36

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51

Dosage Studied

A high-performance liquid chromatography procedure for the simultaneous determination of aminophylline, methoxyphenamine hydrochloride, noscapine and chlorphenamine maleate has been developed and validated. Lewis rats (n = 7 or 8), models of human extensive and poor metabolizer phenotypes of debrisoquine/sparteine, respectively, were dosed with methoxymhenamine with and without prior administration of quinidine.

ExcerptRelevanceReference
" Lewis rats (n = 7 or 8) were dosed with methoxyphenamine with and without prior administration of various doses of either quinine or its diastereomer quinidine."( Quinine is a more potent inhibitor than quinidine in rat of the oxidative metabolic routes of methoxyphenamine which involve debrisoquine 4-hydroxylase.
Hawes, EM; McKay, G; Midha, KK; Muralidharan, G, 1991
)
0.77
" Lewis and Dark Agouti (DA) rat strains (n = 4), models of human extensive and poor metabolizer phenotypes of debrisoquine/sparteine, respectively, were dosed with methoxyphenamine with and without prior administration of quinidine."( Selective in vivo inhibition by quinidine of methoxyphenamine oxidation in rat models of human debrisoquine polymorphism.
Hawes, EM; Inaba, T; McKay, G; Midha, KK; Muralidharan, G, 1989
)
0.73
" (iv) While multiple dosing and pregnancy did not alter either the urinary recovery or profile of the metabolites detected, there was a linear decrease in the MPA:ODMP ratio during gestation."( The influence of pregnancy on the biotransformation and urinary excretion of methoxyphenamine in mice.
Buttar, HS; Cyr, TD; Foster, BC; Moffatt, J; Wilson, DL, 1995
)
0.52
" The drug excreted into beard was detected 10 approximately 12 days for a single dose and 12-14 days for 7 doses after the last dosage at the cut off level of 1 ng/mg."( Hair analysis for drugs of abuse. VI. The excretion of methoxyphenamine and methamphetamine into beards of human subjects.
Konuma, K; Nakahara, Y; Takahashi, K, 1993
)
0.53
"A high-performance liquid chromatography procedure for the simultaneous determination of aminophylline, methoxyphenamine hydrochloride, noscapine and chlorphenamine maleate in commercially available compound capsule dosage forms has been developed and validated."( HPLC determination of aminophylline, methoxyphenamine hydrochloride, noscapine and chlorphenamine maleate in compound dosage forms with an aqueous-organic mobile phase.
Tang, C; Wu, X; Yin, C, 2003
)
0.81
" Treatment groups received different dosage of MC (3, 9, and 27 mg daily, MC group) or prednisone (0."( Anti-inflammatory effect of methoxyphenamine compound in rat model of chronic obstructive pulmonary disease.
Bai, CX; Chen, J; Hong, QY; Wang, YH, 2003
)
0.61
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
beta-adrenergic agonistAn agent that selectively binds to and activates beta-adrenergic receptors.
bronchodilator agentAn agent that causes an increase in the expansion of a bronchus or bronchial tubes.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
amphetaminesAmines that constitute a class of central nervous system stimulants based on the structure of the parent amphetamine 1-phenylpropan-2-amine.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (2)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
cytochrome P450 2D6Homo sapiens (human)Potency15.48710.00108.379861.1304AID1645840
activating transcription factor 6Homo sapiens (human)Potency4.77160.143427.612159.8106AID1159516
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (40)

Assay IDTitleYearJournalArticle
AID1347108qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh41 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347424RapidFire Mass Spectrometry qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1)2019The Journal of biological chemistry, 11-15, Volume: 294, Issue:46
Physiologically relevant orthogonal assays for the discovery of small-molecule modulators of WIP1 phosphatase in high-throughput screens.
AID1347425Rhodamine-PBP qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1)2019The Journal of biological chemistry, 11-15, Volume: 294, Issue:46
Physiologically relevant orthogonal assays for the discovery of small-molecule modulators of WIP1 phosphatase in high-throughput screens.
AID1347099qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for NB1643 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1347100qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for LAN-5 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347407qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: primary screen against the NCATS Pharmaceutical Collection2020ACS chemical biology, 07-17, Volume: 15, Issue:7
High-Throughput Screening to Identify Inhibitors of the Type I Interferon-Major Histocompatibility Complex Class I Pathway in Skeletal Muscle.
AID1347096qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for U-2 OS cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347097qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Saos-2 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1347090qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for DAOY cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347104qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for RD cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347098qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SK-N-SH cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347103qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for OHS-50 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347106qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for control Hh wild type fibroblast cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347093qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SK-N-MC cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347094qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for BT-37 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347095qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for NB-EBc1 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347107qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh30 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347101qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for BT-12 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347092qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for A673 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347089qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for TC32 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347102qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh18 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID1347091qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SJ-GBM2 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347105qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for MG 63 (6-TG R) cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1903439Binding affinity to immobilized Halo tag-fused beta2 adrenoceptor (unknown origin) expressed in Escherichia coli BL21 (DE3) by receptor chromatography
AID1903441Binding affinity to immobilized Halo tag-fused beta2 adrenoceptor (unknown origin) expressed in Escherichia coli BL21 (DE3) assessed as association rate constant by receptor chromatography
AID1903437Binding affinity to immobilized Halo tag-fused beta2 adrenoceptor (unknown origin) expressed in Escherichia coli BL21 (DE3) assessed as retention time by chromatography
AID781325pKa (acid-base dissociation constant) as determined by Liao ref: J Chem Info Model 20092014Pharmaceutical research, Apr, Volume: 31, Issue:4
Comparison of the accuracy of experimental and predicted pKa values of basic and acidic compounds.
AID1873863Displacement of [3H]-CGP12,177 from immobilized Halo tag-fused beta2 adrenoceptor (unknown origin) expressed in Escherichia coli BL21 (DE3)
AID1903440Binding affinity to immobilized Halo tag-fused beta2 adrenoceptor (unknown origin) expressed in Escherichia coli BL21 (DE3) assessed as dissociation rate constant by receptor chromatography
AID1873862Binding affinity to immobilized Halo tag-fused beta2 adrenoceptor (unknown origin) expressed in Escherichia coli BL21 (DE3) assessed as retention time by chromatographic analysis
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (57)

TimeframeStudies, This Drug (%)All Drugs %
pre-199022 (38.60)18.7374
1990's9 (15.79)18.2507
2000's6 (10.53)29.6817
2010's9 (15.79)24.3611
2020's11 (19.30)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 41.82

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index41.82 (24.57)
Research Supply Index4.19 (2.92)
Research Growth Index4.66 (4.65)
Search Engine Demand Index58.83 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (41.82)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (1.56%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other63 (98.44%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]