Page last updated: 2024-12-07

p-methoxy-n-methylphenethylamine

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

Description

p-Methoxy-N-methylphenethylamine: A potent mast cell degranulator. It is involved in histamine release. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

N,O-dimethyltyramine : A secondary amino compound that is tyramine in which the hydrogen of the phenolic hydroxy group has been replaced by a methyl group. [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 CID104735
CHEBI ID75143
SCHEMBL ID681498
MeSH IDM0351213

Synonyms (49)

Synonym
AC-2678
c10h15no
p-methoxy-n-methylphenethylamine
n-(p-methoxyphenethyl)methylamine
benzeneethanamine, 4-methoxy-n-methyl-
compound 48-80
brn 2413387
phenethylamine, p-methoxy-n-methyl-
4-methoxy-n-methylbenzeneethanamine
4091-50-3
AKOS000256616
2-(4-methoxyphenyl)-n-methylethanamine
[2-(4-methoxy-phenyl)-ethyl]-methyl-amine
n-methyl 4-methoxyphenethylamine
n-methyl-p-methoxyphenethylamine
4-methoxy-n-methylphenethylamine
n,o-dimethyltyramine
CHEBI:75143
n-[2-(4-methoxyphenyl)ethyl]-n-methylamine
3-13-00-01640 (beilstein handbook reference)
j18pf78jwq ,
unii-j18pf78jwq
AB07595
n-methyl-4-methoxyphenethylamine
n-methyl-n-[2-(4-methoxy-phenyl)-ethyl]-amine
4-methoxyphenethyl-n-methyl-amine
n-(4-methoxy-phenylethyl)-n-methyl-amine
4-methoxy-n-methylbenzene-ethanamine
JCMWSVNNSPUNER-UHFFFAOYSA-N
n-methyl-beta-(4-methoxyphenyl)-ethylamine
SCHEMBL681498
SY002518
mfcd00870496
2-(4-methoxyphenyl)-n-methyl-ethanamine
[2-(4-methoxyphenyl)ethyl](methyl)amine
TS-00131
F2158-0907
n-methyl-n-[2-(4-methoxy-phenyl)-ethyl]amine
M2551
n-methyl-2-(4-methoxyphenyl)ethylamine
4-[2-(methylamino)ethyl]anisole
n-methyl-2-(4-methoxyphenyl)ethylamine 95%
n-methyl-4-methoxy-.beta.-phenethylamine
DTXSID80193904
Q27145146
1-(3,3-diphenylpropyl)piperidiniumchloride
FT-0725901
n-methyl-b-(4-methoxyphenyl)ethylamine
EN300-173175

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" In numerous tests no evidence of central activity was found and toxicity studies have shown astemizole to be a very safe drug despite of its long duration of action."( The pharmacological profile of a specific, safe, effective and non-sedative anti-allergic, astemizole.
Awouters, F; Janssen, PA; Niemegeers, CJ, 1986
)
0.27
") injection of pure water has any permanent, damaging toxic sequelae."( Peritoneal toxicity of water: a model of chronic peritonitis caused by osmotic dysequilibrium in rats.
Levine, S; Saltzman, A,
)
0.13
" Our data demonstrate that C48/80 is a safe and effective adjuvant, when used by the intradermal route, to induce protective antibody and balanced Th1/Th2/Th17 responses."( The mast cell activator compound 48/80 is safe and effective when used as an adjuvant for intradermal immunization with Bacillus anthracis protective antigen.
Abraham, SN; Hale, LP; McGowen, AL; Shelburne, CP; Staats, HF, 2009
)
0.35

Compound-Compound Interactions

ExcerptReferenceRelevance
" Nicardipine and two new cardiotonic agents, APP 201-533 and DPI 201-106, interact with the N-terminal domain of troponin C, and either do not affect or, in the case of DPI 201-106, slightly increase the affinity of the Ca(2+)-specific site of troponin C for Ca2+ ion."( Drug interaction with cardiac and skeletal muscle troponin C.
Geguchadze, RN; Gusev, NB; Krylatov, AV, 1990
)
0.28

Bioavailability

ExcerptReferenceRelevance
" These results indicate that PtP may possess strong antianaphylactic activity and suggest that differences in bioavailability may cause differential activity following different administration routes."( Inhibition of mast cell-dependent anaphylactic reactions by the pigment of Polygonum tinctorium (Chung-Dae) in rats.
Hong, DR; Kim, HM; Lee, EH, 1998
)
0.3
" These results indicate that SPAE may possess strong antiallergic activity and suggest that differences in bioavailability may cause differential activity following different administration routes."( Inhibition of immediate-type allergic reactions by the aqueous extract of Salvia plebeia.
Kim, HM; Shi, TY, 2002
)
0.31
"Nilotinib is a new orally bioavailable potent tyrosine kinase inhibitor that is used for the treatment of BCR-ABL-positive chronic myelogenous leukemia."( Anti-allergic effects of nilotinib on mast cell-mediated anaphylaxis like reactions.
El-Agamy, DS, 2012
)
0.38
"6b,11b-Dihydroxy-6b,11b-dihydro-7H-indeno[1,2-b]naphtho[2,1-d]furan-7-one (DHFO), an easily synthesisable, orally bioavailable and relatively non-toxic small molecule synthesised in our lab, was previously reported to possess anti-oxidant, 5-lipoxygenase inhibitory, anti-inflammatory and peripheral analgesic activities."( 6b,11b-Dihydroxy-6b,11b-dihydro-7H-indeno[1,2-b]naphtho[2,1-d]furan-7-one (DHFO), a small molecule targeting NF-κB, demonstrates therapeutic potential in immunopathogenic chronic inflammatory conditions.
Durgashivaprasad, E; Jacob, A; Mathew, G; Reddy, ND; Unnikrishnan, MK, 2013
)
0.39

Dosage Studied

ExcerptRelevanceReference
" Analysis of the specificity of drug activity depends upon dose-response studies, species differences and consideration of nonspecific systemic effects."( An analysis of the specificity in pharmacological inhibition of the passive cutaneous anaphylaxis reaction in mice and rats.
Blancuzzi, V; Oronsky, AL; Perper, RJ, 1975
)
0.25
"027 mug/ml within 3 min, which was not futher enhanced on increasing the dosage of L-3 to 1 mg/kg."( Blood histamine levels and arteriovenous concentration differences after the intravenous administration of the basic compounds l-3 and 48/80 in the anaesthetized dog.
Kolassa, N; Kraupp, O; Schütz, W, 1975
)
0.25
" Dose-response curves of the muM cromolyn inhibition of PS-potentiated release revealed a parallel shift, suggesting that cromolyn may compete with PS."( Relationship between phosphatidylserine and cromolyn in histamine release.
Goth, A; Knoohuizen, M; Read, GW, 1977
)
0.26
" The dose-response curve, the latent period and temperature dependence of HR induced by MCD-peptide were similar to those of HR induced by compound 48/80."( [Histamine-liberating action of MCD-peptide from bee venom].
Gushchin, IS; Martynov, VI; Miroshnikov, AI, 1977
)
0.26
"5 and 3 microgram of BAC per ml caused parallel shifts of the 48/80 dose-response curves to the right with no loss of efficacy, indicating that the antagonism was surmountable."( Benzalkonium chloride: selective inhibitor of histamine release induced by compound 48/80 and other polyamines.
Kiefer, EF; Read, GW, 1979
)
0.26
"In a controlled study, a 1-week course of a moderate dosage of corticosteroids given to ragweed-sensitive subjects was associated with a statistically significant decrease in blood eosinophi, levels and tissue esosinophil, but not mast cell, responses to ragweed antibody levels or gross whealing responses to antigen or compound 48/80."( Histologic studies of human skin test responses to ragweed and compound 48/80. II. Effects of corticosteroid therapy.
Slott, RI; Zeweiman, B, 1975
)
0.25
" The dose-response curves for the compound 48/80-induced release of endogenous Hi and for the various amines taken up by the cells were compared."( Intracellular distribution of amines taken up by rat mast cells.
Bergendorff, A, 1975
)
0.25
" Two of these methods provide different insights, demonstrating different patterns of response to dosage and over time, produced by different agents."( Patterns of angiogenic response to mast cell granule constituents.
Brown, FI; Duncan, JI; Long, WF; McKinnon, A; Thompson, WD; Williamson, FB, 1992
)
0.28
" Significant dose-response relationships were found between histamine concentration and each of ID, Imax, Tii and flare in both patients and controls."( Patients' perception of itch induced by histamine, compound 48/80 and wool fibres in atopic dermatitis.
Bergström, R; Hägermark, O; Wahlgren, CF, 1991
)
0.28
" Dose-response studies of peritoneal and pleural mast cells purified with Percoll and Ficoll and stimulated by polymyxin B showed a decreased sensitivity and decreased maximum response of peritoneal cells when Percoll was used."( Difference in, and influence of the purification medium on, sensitivity and maximum response of peritoneal and pleural mast cells stimulated by certain polyamines.
Botana, LM; Eleno, N; Espinosa, J; Fernández-Otero, P; Segura, C, 1985
)
0.27
"6 micrograms/ml, computer-derived from the dose-response data."( Effect of the mast cell activator compound 48/80 and heparin on angiogenesis in the chick chorioallantoic membrane.
Clinton, M; Duncan, JI; Long, WF; Thompson, WD; Williamson, FB, 1988
)
0.27
" In both groups a clear dose-response relationship was demonstrated by either reagent."( Skin reactions to histamine and compound 48/80 in chronic urticaria: a diagnostic tool?
Gonzalo Reques, F; Ortega Núñez, A; Pelta-Fernández, R; Rubio Sotes, M,
)
0.13
" The dose-response curves were sigmoid-like in linear-log plots."( On the 48/80-induced secretion of tissue mast cells and its mitogenic effect on nearby cells in the intact rat.
Norrby, K, 1981
)
0.26
" The dose-response curve for the neurotensin effect was triphasic: and initial gentle rise, a plateau (2."( Histamine release induced by neurotensin from rat peritoneal mast cells.
Kurose, M; Saeki, K, 1981
)
0.26
" In contrast to 48/80, the dose-response curves for histamine and serotonin release were parallel."( Compound 48/80 and substance P induced release of histamine and serotonin from rat peritoneal mast cells.
Erjavec, F; Irman-Florjanc, T, 1983
)
0.27
" A dose-response for degranulation by compound 48/80 was performed and it was shown that azure A staining (in 40% sucrose) discriminates degranulated from non-degranulated mast cells, while trypan blue staining discriminates between cytotoxic and non-cytotoxic degranulation."( Determination of rat mast cells by flow-cytometry.
De Weck, AL; Nakagawa, T; Stadler, BM, 1980
)
0.26
" However, the dose-response curves to adenosine were shifted to the left in arterioles constricted by either stunning, compound 48/80, exposure to cold superfusate, or cromolyn compared with control vessels."( Arteriolar constriction in skeletal muscle during vascular stunning: role of mast cells.
Keller, MW, 1997
)
0.3
" Mast cell degranulation studies were done by using compound 48/80 as degranulation agent with same dosage schedule."( Evaluation of antiallergic activity (type I hypersensitivity) of Inula racemosa in rats.
Ali, B; Dixit, KS; Gupta, PP; Misra, G; Palit, G; Prasad, R; Saxena, RC; Srivastava, S, 1999
)
0.3
" In the dose-response curves of the four herbs, the logarithmic linearity was observed for each herb, and 50% inhibitory concentration, the IC50 values, were calculated to be 56."( Effects of an oriental herbal medicine, "Saiboku-to", and its constituent herbs on Compound 48/80-induced histamine release from peritoneal mast cells in rats.
Ikarashi, Y; Ishimaru, H; Maruyama, Y; Sakakibara, I; Takahashi, A; Yuzurihara, M, 2001
)
0.31
" Ex vivo experiments aimed at evaluating the capacity of heparin to prevent histamine release in rat mast cells indicated that the free or encapsulated drug exhibited the same dose-response behaviour."( Chitosan-hyaluronic acid nanoparticles loaded with heparin for the treatment of asthma.
Alonso, MJ; Brea, J; Loza, MI; Oyarzun-Ampuero, FA; Torres, D, 2009
)
0.35
" After 30 min, 6h, and 24-72 h, the rings were suspended in an organ bath and dose-response curve to methacholine (MCh) were determined."( Connective tissue mast cells are the target of formaldehyde to induce tracheal hyperresponsiveness in rats: putative role of leukotriene B4 and nitric oxide.
Breithaupt-Faloppa, AC; de Oliveira, AP; Domingos, HV; Lino-dos-Santos-Franco, A; Oliveira-Filho, RM; Shia, MK; Tavares-de-Lima, W; Vargaftig, BB, 2010
)
0.36
" Its inhibitory effect was dependent on the dosage and administration period."( Anti-scratching behavioral effect of Lactobacillus plantarum PM008 isolated from kimchi in mice.
Han, MJ; Hyun, YJ; Jang, SE; Kim, DH; Trinh, HT, 2011
)
0.37
" Compound 48/80 induced concentration-related contraction in all the examined strips following a sigmoidal dose-response curve fit."( Degranulation of mast cells due to compound 48/80 induces concentration-dependent intestinal contraction in rainbow trout (Oncorhynchus mykiss Walbaum) ex vivo.
Borreca, C; Dezfuli, BS; Giammarino, A; Giari, L; Manera, M, 2011
)
0.37
" The results showed that the serum IgG titers of all of the mice immunized with NP reached a higher level and the protection provided by NP vaccine against the homologous virus depended on the administered dosage and adjuvant."( Cross-protection against influenza virus infection by intranasal administration of nucleoprotein-based vaccine with compound 48/80 adjuvant.
Chen, Z; Fang, F; Liu, F; Shen, Y; Sun, B; Wang, S; Xie, Z; Xu, W; Zheng, M, 2015
)
0.42
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
[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 (2)

ClassDescription
secondary amino compoundA compound formally derived from ammonia by replacing two hydrogen atoms by organyl groups.
aromatic etherAny ether in which the oxygen is attached to at least one aryl substituent.
[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]

Research

Studies (2,532)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901460 (57.66)18.7374
1990's526 (20.77)18.2507
2000's330 (13.03)29.6817
2010's185 (7.31)24.3611
2020's31 (1.22)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 6.32

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index6.32 (24.57)
Research Supply Index7.89 (2.92)
Research Growth Index4.21 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (6.32)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials38 (1.44%)5.53%
Reviews33 (1.25%)6.00%
Case Studies6 (0.23%)4.05%
Observational0 (0.00%)0.25%
Other2,557 (97.08%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]