Page last updated: 2024-11-04

tripelennamine

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

Description

Tripelennamine: A histamine H1 antagonist with low sedative action but frequent gastrointestinal irritation. It is used to treat ASTHMA; HAY FEVER; URTICARIA; and RHINITIS; and also in veterinary applications. Tripelennamine is administered by various routes, including topically. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5587
CHEMBL ID1241
CHEBI ID9741
SCHEMBL ID17970
MeSH IDM0022012

Synonyms (132)

Synonym
n-benzyl-n-[2-(dimethylamino)ethyl]pyridin-2-amine
BRD-K57033106-048-02-8
benzyl-(.alpha.-pyridyl)-dimethylaethylendiamin
tripelennamin
n,n-dimethyl-n'-benzyl-n'-(.alpha.-pyridyl)ethylenediamine
piribenzil
wln: t6nj bn1r&2n1&1 &gh
nsc-118946
nsc118946
resistamine
tonaril
.beta.-dimethylaminoethyl-2-pyridylbenzylamine
2-[n-benzyl-n-(2-dimethylaminoethyl)amino]pyridine
tripelenamine
wln: t6nj bn1r&2n1&1
benzyl-.alpha.-pyridyl-dimethyl-aethylendiamin
tripelannamine
n,n-dimethyl-n'-benzyl-n'-(2-pyridyl)ethylenediamine
pyridine, 2-[benzyl[2-(dimethylamino)ethyl]amino]-
pyristine (piristina)
n-benzyl-n',n'-dimethyl-n-(2-pyridyl)ethylenediamine
1, n,n-dimethyl-n'-(phenylmethyl)-n'-2-pyridinyl-
pyribenzamin
benzoxale
.beta.-dimethylaminoethyl-2-pyridylaminotoluene
pyribenzamine
2-[benzyl(2-dimethylaminoethyl)amino]pyridine
pyrinamine base
n-benzyl-n',n'-dimethyl-n-2-(pyridylethylene)diamine
cizaron
n-benzyl-n-(2-pyridyl)-n',n'-dimethyl ethylenediamine
1,2-ethanediamine, n,n-dimethyl-n'-(phenylmethyl)-n'-2-pyridinyl-
DIVK1C_000534
KBIO1_000534
n,n-dimethyl-n'-(phenylmethyl)-n'-pyridin-2-ylethane-1,2-diamine
SPECTRUM_000141
tripelennaminum [inn-latin]
beta-dimethylaminoethyl-2-pyridylbenzylamine
n,n-dimethyl-n'-benzyl-n'-(alpha-pyridyl)ethylenediamine
vetibenzamina
nci-c60662
tripelennamine [inn]
tripelennamina [italian]
benzyl-(alpha-pyridyl)-dimethylaethylendiamin [german]
pyridine, 2-(benzyl(2-(dimethylamino)ethyl)amino)-
tripelenamina [inn-spanish]
brn 0227074
hsdb 5191
ts and blues
2-(benzyl(2-dimethylaminoethyl)amino)pyridine
nsc 118946
beta-dimethylaminoethyl-2-pyridylaminotoluene
2-(n-benzyl-n-(2-dimethylaminoethyl)amino)pyridine
n,n-dimethyl-n'-(phenylmethyl)-n'-2-pyridinyl-1,2-ethanediamine
einecs 202-100-1
n-benzyl-n',n'-dimethyl-n-2-pyridylethylenediamine
ethylenediamine, n-benzyl-n',n'-dimethyl-n-(2-pyridyl)-
SPECTRUM5_001581
BSPBIO_003252
C07180
tripelennamine
91-81-6
DB00792
2-(benzyl(2-(dimethylamino)ethyl)amino)pyridine
KBIOSS_000621
KBIOGR_000867
KBIO2_000621
KBIO2_005757
KBIO2_003189
KBIO3_002472
SPECTRUM4_000374
SPECTRUM3_001696
SPBIO_000954
SPECTRUM2_000957
NINDS_000534
IDI1_000534
OPREA1_266730
NCGC00018125-01
CHEMBL1241
chebi:9741 ,
L000603
D08645
tripelennamine (inn)
n'-benzyl-n,n-dimethyl-n'-pyridin-2-ylethane-1,2-diamine
bdbm81471
nsc_5587
cas_91-81-6
NCGC00018125-03
NCGC00018125-02
triplennamine
tripellenamine
pyridbenzamine
5-22-08-00378 (beilstein handbook reference)
tripelennaminum
2750 r.p.
tripelenamina
benzyl-(alpha-pyridyl)-dimethylaethylendiamin
unii-3c5oro99ty
tripelennamine [inn:ban]
tripelennamina
3c5oro99ty ,
tripelennamine [hsdb]
tripelennamine [vandf]
tripelennamine [mi]
tripelennamine [who-dd]
n-benzyl-n',n'-dimethyl-n-pyridin-2-ylethane-1,2-diamine
gtpl7318
SCHEMBL17970
recovr (salt/mix)
stanzamine (salt/mix)
dehistin (salt/mix)
UFLGIAIHIAPJJC-UHFFFAOYSA-N
antiallergicum medivet (salt/mix)
ahistamin (salt/mix)
tri-tumine (salt/mix)
AB00053562_13
AB00053562_14
1,2-ethanediamine,n1,n1-dimethyl-n2-(phenylmethyl)-n2-2-pyridinyl-
DTXSID8023717 ,
SBI-0051548.P002
Q415203
n'-benzyl-n,n-dimethyl-n'-pyridin-2-ylethane-1,2-diamine;hydron;chloride
BRD-K57033106-048-03-6
EN300-708778
HY-17428A
CS-0009189
tripelennamine 1000 microg/ml in acetonitrile
d04aa04
tripelenamina (inn-spanish)
tripelennaminum (inn-latin)
r06ac04
dtxcid803717

Research Excerpts

Actions

ExcerptReferenceRelevance
"Tripelennamine did not suppress morphine withdrawal signs, but rather aggravated them."( Pentazocine-tripelennamine ("T's and Blues") substitution studies in morphine-dependent rodents.
Carter, WH; Dewey, WL; Kachur, JF; Tagashira, E, 1984
)
1.37

Treatment

Pretreatment with tripelennamine and HCl prevented the effect of histamine on the afferent EN activity. Pretreatment with cimetidine (histamine H2-receptor antagonist) or propranolol (beta-adrenoceptor antagonist, 10 mg/kg i.p.) had no effect.

ExcerptReferenceRelevance
"Pretreatment with tripelennamine and HCl prevented the effect of histamine on the afferent EN activity; but after cimetidine and HCl pretreatment histamine still had a marked stimulant effect."( Does histamine stimulate trigeminal nasal afferents?
Kuwahara, M; Sekizawa, S; Sugano, S; Tsubone, H, 1998
)
0.62
"Pretreatment with tripelennamine (histamine H1-receptor antagonist, 40 mg/kg i.p.) prior to the administration of compound 48/80 reduced the effect of compound 48/80 on drinking, but pretreatment with cimetidine (histamine H2-receptor antagonist, 40 mg/kg i.p.) or propranolol (beta-adrenoceptor antagonist, 10 mg/kg i.p.) had no effect."( The role of the renin-angiotensin system in compound 48/80-induced thirst in rats.
Hayakari, M; Izumi, H, 1986
)
0.59

Compound-Compound Interactions

Tp alone produced antinociception (ANTI) in mice and also caused potentiation when combined with morphine (M) or nalbuphene (NB) These results are similar to previous results obtained with tripelennamine and pentazocine suggesting that nalbuphine may have abuse potential.

ExcerptReferenceRelevance
" These results are similar to previous results obtained with tripelennamine and pentazocine suggesting that nalbuphine may have abuse potential if combined with tripelennamine."( Effects of nalbuphine alone and in combination with tripelennamine on rewarding brain stimulation thresholds in the rat.
Kornetsky, C; Unterwald, EM, 1986
)
0.76
" Studies revealed that tripelennamine (Tp) alone produced antinociception (ANTI) in mice and also caused potentiation when combined with morphine (M) or nalbuphene (NB)."( The effect of tripelennamine alone and in combination with opiates to produce antinociception in mice.
Hanig, JP; Hui, FW; Sun, CJ; Tocus, EC, 1983
)
0.94

Dosage Studied

Dose-response relationships to histamine were done in rings of canine pulmonary artery from heartworm and control dogs. Tripelennamine was responsible for the inhibitory activity, which was partially antagonized by pentazocine.

ExcerptRelevanceReference
" Concurrent dosing of pentazocine (2 mg/kg, IP) and tripelennamine (2."( Potentiation of pentazocine conditioned place preference by tripelennamine in rats.
Masukawa, Y; Misawa, M; Shiozaki, Y; Suzuki, T, 1991
)
0.77
" All three antihistaminics, at some dosage levels, slightly increased activity when given alone, but strongly enhanced morphine-induced hyperactivity."( Enhancement of morphine-induced hyperactivity by antihistaminic drugs in mice.
Castellano, C; D'Amato, FR; Sansone, M, 1986
)
0.27
" All three antihistaminics, at some dosage levels, enhanced morphine-induced hyperactivity, but did not change or even reduce locomotor stimulation induced by amphetamine and scopolamine."( Antihistaminics enhance morphine-, but not amphetamine- and scopolamine-induced hyperactivity in mice.
D'Udine, B; Renzi, P; Sansone, M; Vetulani, J, 1987
)
0.27
" Dose-response curves (derived from the results of using the tablets as well as pure powders) showed that tripelennamine was responsible for the inhibitory activity, which was partially antagonized by pentazocine."( Selective survival in pentazocine and tripelennamine of Pseudomonas aeruginosa serotype O11 from drug addicts.
Botsford, KB; Kabins, SA; Nathan, CR; Weinstein, RA, 1985
)
0.75
"Quantal dose-response curves were generated to determine the median lethal doses (LD50S) for pentazocine and tripelennamine, either alone or in combination."( Potentiation of lethality in mice by combinations of pentazocine and tripelennamine.
Katz, NL; Morris, RW; Waller, DP, 1980
)
0.71
" Dose-response relationships to histamine were done in rings of canine pulmonary artery from heartworm and control dogs, in the presence and absence of endothelial cells, the H1 receptor blocker tripelennamine, or the H2 receptor blocker cimetidine."( Dirofilaria immitis: heartworm infection converts histamine-induced constriction to endothelium-dependent relaxation in canine pulmonary artery.
Kaiser, L; Williams, JF, 1998
)
0.49
" Whole EN activity was not stimulated even by the highest dose (1 x 10(-1) M) of histamine when the nose was pretreated with saline, but was substantially stimulated by histamine in a dose-response fashion (1 x 10(-2) M) after pretreatment with HCI or H2SO4."( Does histamine stimulate trigeminal nasal afferents?
Kuwahara, M; Sekizawa, S; Sugano, S; Tsubone, H, 1998
)
0.3
" This occurs despite clinicians' attention to patient medical histories, aspiration of the local anesthetic syringe during injections, and minimizing the dosage of local anesthetic solutions."( Managing patients with local anesthetic complications using alternative methods.
Lu, DP,
)
0.13
" dosage exerted a small but measurable anti-whealing effect five hours after ingestion."( Studies of the "antihistaminic" effect of pyribenzamine administered by various routes.
LeVAN, P; PERRY, DJ; STERNBERG, TH, 1951
)
0.23
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
aromatic amineAn amino compound in which the amino group is linked directly to an aromatic system.
[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]

Pathways (1)

PathwayProteinsCompounds
Tripelennamine H1-Antihistamine Action87

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Histamine H1 receptorRattus norvegicus (Norway rat)IC50 (µMol)0.03980.00000.32271.2589AID87362
Histamine H1 receptorRattus norvegicus (Norway rat)Ki100,000,000,376,832.00000.00071.54406.5000AID87372
Histamine H1 receptorHomo sapiens (human)IC50 (µMol)0.03980.00000.44365.1768AID87362
Histamine H1 receptorHomo sapiens (human)Ki100,000,000,376,832.00000.00000.511010.0000AID87372
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (12)

Processvia Protein(s)Taxonomy
inflammatory responseHistamine H1 receptorHomo sapiens (human)
G protein-coupled receptor signaling pathwayHistamine H1 receptorHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayHistamine H1 receptorHomo sapiens (human)
memoryHistamine H1 receptorHomo sapiens (human)
visual learningHistamine H1 receptorHomo sapiens (human)
regulation of vascular permeabilityHistamine H1 receptorHomo sapiens (human)
positive regulation of vasoconstrictionHistamine H1 receptorHomo sapiens (human)
regulation of synaptic plasticityHistamine H1 receptorHomo sapiens (human)
cellular response to histamineHistamine H1 receptorHomo sapiens (human)
G protein-coupled serotonin receptor signaling pathwayHistamine H1 receptorHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerHistamine H1 receptorHomo sapiens (human)
chemical synaptic transmissionHistamine H1 receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (3)

Processvia Protein(s)Taxonomy
histamine receptor activityHistamine H1 receptorHomo sapiens (human)
G protein-coupled serotonin receptor activityHistamine H1 receptorHomo sapiens (human)
neurotransmitter receptor activityHistamine H1 receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
cytosolHistamine H1 receptorHomo sapiens (human)
plasma membraneHistamine H1 receptorHomo sapiens (human)
synapseHistamine H1 receptorHomo sapiens (human)
dendriteHistamine H1 receptorHomo sapiens (human)
plasma membraneHistamine H1 receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (37)

Assay IDTitleYearJournalArticle
AID1145710Inhibition of acetylcholine-induced contraction in guinea pig ileum at 0.1 uM treated for 15 mins prior to acetylcholine challenge1976Journal of medicinal chemistry, Jan, Volume: 19, Issue:1
Conformationally restricted analogs of histamine H1 receptor antagonists: trans and cis-1-benzyl-3-dimethylamino-6-phenylpiperidine.
AID624609Specific activity of expressed human recombinant UGT1A62000Annual review of pharmacology and toxicology, , Volume: 40Human UDP-glucuronosyltransferases: metabolism, expression, and disease.
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID87227Intrinsic activity was determined2003Journal of medicinal chemistry, Dec-18, Volume: 46, Issue:26
Synthesis and pharmacological identification of neutral histamine H1-receptor antagonists.
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID43581Inhibition of beta-lactamase at 100 uM2003Journal of medicinal chemistry, Oct-09, Volume: 46, Issue:21
Identification and prediction of promiscuous aggregating inhibitors among known drugs.
AID624616Specific activity of expressed human recombinant UGT2B152000Annual review of pharmacology and toxicology, , Volume: 40Human UDP-glucuronosyltransferases: metabolism, expression, and disease.
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID624612Specific activity of expressed human recombinant UGT1A92000Annual review of pharmacology and toxicology, , Volume: 40Human UDP-glucuronosyltransferases: metabolism, expression, and disease.
AID106806Inhibition of malate dehydrogenase (MDH) at 400 uM2003Journal of medicinal chemistry, Oct-09, Volume: 46, Issue:21
Identification and prediction of promiscuous aggregating inhibitors among known drugs.
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID87362Inhibitory activity against human Histamine H1 receptor2003Journal of medicinal chemistry, Dec-18, Volume: 46, Issue:26
Synthesis and pharmacological identification of neutral histamine H1-receptor antagonists.
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID624608Specific activity of expressed human recombinant UGT1A42000Annual review of pharmacology and toxicology, , Volume: 40Human UDP-glucuronosyltransferases: metabolism, expression, and disease.
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID87372Inhibitory activity against human Histamine H1 receptor2003Journal of medicinal chemistry, Dec-18, Volume: 46, Issue:26
Synthesis and pharmacological identification of neutral histamine H1-receptor antagonists.
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID52790Inhibition of chymotrypsin at 250 uM2003Journal of medicinal chemistry, Oct-09, Volume: 46, Issue:21
Identification and prediction of promiscuous aggregating inhibitors among known drugs.
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID624607Specific activity of expressed human recombinant UGT1A32000Annual review of pharmacology and toxicology, , Volume: 40Human UDP-glucuronosyltransferases: metabolism, expression, and disease.
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID588220Literature-mined public compounds from Kruhlak et al phospholipidosis modelling dataset2008Toxicology mechanisms and methods, , Volume: 18, Issue:2-3
Development of a phospholipidosis database and predictive quantitative structure-activity relationship (QSAR) models.
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1145708Antagonist activity at histamine H1 receptor in guinea pig ileum assessed as inhibition of histamine-induced contraction at 0.1 uM treated for 15 mins prior to histamine challenge1976Journal of medicinal chemistry, Jan, Volume: 19, Issue:1
Conformationally restricted analogs of histamine H1 receptor antagonists: trans and cis-1-benzyl-3-dimethylamino-6-phenylpiperidine.
AID588208Literature-mined public compounds from Lowe et al phospholipidosis modelling dataset2010Molecular pharmaceutics, Oct-04, Volume: 7, Issue:5
Predicting phospholipidosis using machine learning.
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID624606Specific activity of expressed human recombinant UGT1A12000Annual review of pharmacology and toxicology, , Volume: 40Human UDP-glucuronosyltransferases: metabolism, expression, and disease.
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
AID1346037Human H1 receptor (Histamine receptors)2003Journal of medicinal chemistry, Dec-18, Volume: 46, Issue:26
Synthesis and pharmacological identification of neutral histamine H1-receptor antagonists.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (666)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990617 (92.64)18.7374
1990's32 (4.80)18.2507
2000's13 (1.95)29.6817
2010's4 (0.60)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 47.71

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 Index47.71 (24.57)
Research Supply Index6.61 (2.92)
Research Growth Index3.90 (4.65)
Search Engine Demand Index81.60 (26.88)
Search Engine Supply Index2.07 (0.95)

This Compound (47.71)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials13 (1.78%)5.53%
Reviews8 (1.10%)6.00%
Case Studies27 (3.70%)4.05%
Observational0 (0.00%)0.25%
Other682 (93.42%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]