TRIPELENNAMINE

US Previously Marketed

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H21N3
Molecular Weight	255.358
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN(C)CCN(CC1=CC=CC=C1)C2=CC=CC=N2

InChI

InChIKey=UFLGIAIHIAPJJC-UHFFFAOYSA-N

InChI=1S/C16H21N3/c1-18(2)12-13-19(16-10-6-7-11-17-16)14-15-8-4-3-5-9-15/h3-11H,12-14H2,1-2H3

HIDE SMILES / InChI

Molecular Formula	C16H21N3
Molecular Weight	255.358
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.drugs.com/mtm/tripelennamine.html

Tripelennamine (sold as Pyribenzamine by Novartis) is a drug that is used as an antipruritic and first-generation antihistamine. Histamine acting on H1-receptors produces vasodilatation, hypotension, flushing, headache, tachycardia, and bronchoconstriction. Histamine also increases vascular permeability and potentiates pain. Tripelennamine can be used in the treatment of asthma, hay fever, rhinitis, and urticaria, but is now less common as newer antihistamines have replaced it.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H1 receptor 316 Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7513381	Antagonist 2849

Conditions

Condition	Modality	Highest Phase	Product
Hives 5 Sources: https://www.drugs.com/mtm/tripelennamine.html	Palliative	Approved 8583	PBZ Approved Use Unknown Launch Date 1948
Rashes 5 Sources: https://www.drugs.com/mtm/tripelennamine.html	Palliative	Approved 8583	PBZ Approved Use Unknown Launch Date 1948
Sneezing 7 Sources: https://www.drugs.com/mtm/tripelennamine.html	Palliative	Approved 8583	PBZ Approved Use Unknown Launch Date 1948

C_max

Value	Dose	Co-administered	Analyte	Population
82 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3709032	50 mg single, intramuscular dose: 50 mg route of administration: Intramuscular experiment type: SINGLE co-administered:		TRIPELENNAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
199 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3709032	100 mg single, intramuscular dose: 100 mg route of administration: Intramuscular experiment type: SINGLE co-administered:		TRIPELENNAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
398 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3709032	50 mg single, intramuscular dose: 50 mg route of administration: Intramuscular experiment type: SINGLE co-administered:		TRIPELENNAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
804 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3709032	100 mg single, intramuscular dose: 100 mg route of administration: Intramuscular experiment type: SINGLE co-administered:		TRIPELENNAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3709032	50 mg single, intramuscular dose: 50 mg route of administration: Intramuscular experiment type: SINGLE co-administered:		TRIPELENNAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
4.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3709032	100 mg single, intramuscular dose: 100 mg route of administration: Intramuscular experiment type: SINGLE co-administered:		TRIPELENNAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
100 mg 1 times / day single, oral Studied dose Dose: 100 mg, 1 times / day Route: oral Route: single Dose: 100 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13039563/	healthy, 2 years Health Status: healthy Age Group: 2 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/13039563/	Other AEs: Weakness, Common cold... Other AEs: Weakness Common cold (grade 1) Cough Rhinorrhea Vomiting Sleepiness Sources: https://pubmed.ncbi.nlm.nih.gov/13039563/
25 mg 3 times / day multiple, oral Studied dose Dose: 25 mg, 3 times / day Route: oral Route: multiple Dose: 25 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13526305/	unhealthy, 49 years Health Status: unhealthy Age Group: 49 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/13526305/	Other AEs: Coma, Common cold... Other AEs: Coma Common cold Nausea Diarrhoea Back pain Headache (grade 3) Appetite lost Dry cough Pyrexia Abdominal pain (grade 3) Vomiting Disorientation Sources: https://pubmed.ncbi.nlm.nih.gov/13526305/
50 mg 3 times / day multiple, oral Recommended Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13640851/	unhealthy, median age 36 years Health Status: unhealthy Age Group: median age 36 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/13640851/	Other AEs: Sedation, Sedation... Other AEs: Sedation (grade 1, 8.9%) Sedation (grade 2, 6.7%) Dizziness (5.5%) Nausea (4.4%) Nose dryness (2.2%) Sources: https://pubmed.ncbi.nlm.nih.gov/13640851/

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
		inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	UGT enzymes 27

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 2546	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/9616188/	yes [Ki 4 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
UGT enzymes 27	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/1362943/	yes

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY579204	https://www.001chemical.com/chem/91-81-6
1PlusChem LLC	1P00AOZL
A2B Chem	AE98145
ABI Chem	AC1L1KOH
ABI Chem	AC1Q3WSI
ABI Chem	AC1Q3WSJ
AbovChem LLC	HY-17428
AK Scientific	Y1482
AKOS	AKOS025116925
Alfa Chemistry	91-81-6	https://www.alfa-chemistry.com/cas_91-81-6.htm
Ambeed	A147384
Angene	AGN-PC-0Q6RIZ
ApexBio Technology	B1553
Aurora Fine Chemicals LLC	K02.874.628	http://online.aurorafinechemicals.com/info?ID=K02.874.628
BioSynth	W-108029
BLD Pharm	BD16460
BlocksMatrix Scientific	147893
BOC Sciences	154-69-8
BOC Sciences	6138-56-3
Chem Scene	CS-1395
ChemExper Chemical Directory	jlep@@@XleLl{rkMA^RDEEAAP@@@
Chemieliva Pharmaceutical Co., Ltd	PBCM1043527
ChemMol	99173756	http://www.chemmol.com/chemmol/99173756.html
ChemShuttle	113827
Chemspace	CSC020643506
Combi-Blocks	QP-2860
Compound Cloud	197066
Compound Cloud	5587
Compound Cloud	9066
eMolecules	300002447
eMolecules	595075
eMolecules	979261
Enamine	BBV-78228896
Enamine	EN300-123046
Enamine	EN300-708778
eNovation Chemicals	D763057
Frontier Scientific Services	100082092
Frontier Scientific Services	500028055
Hairui	HR141876	http://www.hairuichem.com/en/product/91-81-6.html
HongKong Chemhere	SCE20729
KeyOrganics	AS-59347
Lab Network	LN00337400
Lab Seeker	SC-94044
mcule	MCULE-1679949518	https://mcule.com/MCULE-1679949518/
MedChem Express	HY-17428
Molcore	MC579204	https://www.molcore.com/product/91-81-6
Molnova	M12195
MolPort	MolPort-003-894-746
MuseChem	I009889
NCI Plated 2007	118946
NCI Plated 2007	409943
Norris Pharm	NSZB-A260011
NovoSeek	5587
PI Chemicals	PI-27214
Ryan Scientific	Estriol
Selleck Chemicals	S3146
Sigma Aldrich	1695004
Sigma Aldrich	1695004\|USP
Sigma Aldrich	R288918\|ALDRICH
Sigma Aldrich	T7511
Sigma Aldrich	T7511\|SIAL
Sinfoo Biotech	S017589	http://www.sinfoobiotech.com/product/1020987
Smolecule	S702025	https://www.smolecule.com/products/s702025
StruChem	SC-94044
Syntharise	SRISEC022
TargetMol	T1269
Tetrahedron	TS35445
TimTec	SBB056873
TimTec	ST50411553
Toronto Research Chemicals	T808325
Yick-Vic Chemicals & Pharmaceuticals (HK) Ltd.	PH-1221A
ZINC	ZINC000019117728	http://zinc15.docking.org/substances/ZINC000019117728

PubMed

Title	Date	PubMed
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011-07-14	21599003
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010-12	21818443
Inappropriate prescribing in the hospitalized elderly patient: defining the problem, evaluation tools, and possible solutions.	2010-04-07	20396637
The use of in vitro technologies coupled with high resolution accurate mass LC-MS for studying drug metabolism in equine drug surveillance.	2010-01	20878880
Anomalous photophysics of H1 antihistamines in aqueous solution.	2009-05-14	19388641
Ruthenium-catalyzed N-alkylation of amines and sulfonamides using borrowing hydrogen methodology.	2009-02-11	19191700
Medullary pain facilitating neurons mediate allodynia in headache-related pain.	2009-02	19259966
Chest swelling and Fever in an intravenous drug user.	2008-05	19561717
Myasthenia gravis-like syndrome in a Hereford heifer.	2008-02-22	18289316
Amoxicillin-Induced Eosinophilic Pneumonia with Granulomatous Reaction: Discrepancy between Drug-Induced Lymphocyte Stimulation Test Findings and the Provocation Drug Test.	2007-06-15	20525146
Characterization of antihistamine-human serum protein interactions by capillary electrophoresis.	2007-04-20	17339039
Analysis of pharmaceutical preparations containing antihistamine drugs by micellar liquid chromatography.	2006-02-13	16182504
Involvement of histamine H1 and H2 receptors in the regulation of STAT-1 phosphorylation: inverse agonism exhibited by the receptor antagonists.	2005-07	15914334
Mast cell--pituitary interaction: modulation by serine phospholipids.	2004-12	15638084
Role of N-methyl-D-aspartate receptors in gastric mucosal blood flow induced by histamine.	2004-09-01	15352220
Treatment of allergic rhinitis during pregnancy.	2004-03-24	15035567
Medicinal plants in Suriname: hypotensive effect of Gossypium barbadense.	2004-03	15025864
Prostaglandin E2 aggravates gastric mucosal injury induced by histamine in rats through EP1 receptors.	2003-12-19	14623033
Synthesis and pharmacological identification of neutral histamine H1-receptor antagonists.	2003-12-18	14667234
Management of rhinitis and asthma in pregnancy.	2003-06	12839108
On the mechanisms underlying histamine induction of gastric mucosal lesions in rats with partial gastric vascular occlusion.	2003-06	12832840
Does the neurotransmitter transporter underlie adaptation at a histaminergic photoreceptor synapse?	2002-10-24	12392180
Managing patients with local anesthetic complications using alternative methods.	2002-08-15	12174527
H1-receptor antagonist, tripelennamine, does not affect arterial hypoxemia in exercising Thoroughbreds.	2002-04	11896018
Inhibitory effects of H1-antihistamines on CYP2D6- and CYP2C9-mediated drug metabolic reactions in human liver microsomes.	2002-02	11936702
Quantitation of antihistamines in pharmaceutical preparations by liquid chromatography with a micellar mobile phase of sodium dodecyl sulfate and pentanol.	2002-01-05	11767132
Histamine H1 and H2 receptor antagonists accelerate skin barrier repair and prevent epidermal hyperplasia induced by barrier disruption in a dry environment.	2001-02	11180002
Antinociceptive and antiedematogenic properties and acute toxicity of Tabebuia avellanedae Lor. ex Griseb. inner bark aqueous extract.	2001	11574048
Nitric oxide, superoxide radicals and mast cells in pathogenesis of indomethacin-induced small intestinal lesions in rats.	1999-03	10210152
Effects of antihistaminics on locomotor activity in mice. Comparison with opiate and amphetamine-induced hyperactivity.	1991	1676005
Antihistaminic-opioid combination: effect on locomotor activity in mice.	1988-09-01	3253717
Antihistaminics enhance morphine-, but not amphetamine- and scopolamine-induced hyperactivity in mice.	1987	2892221
Enhancement of morphine-induced hyperactivity by antihistaminic drugs in mice.	1986-12	2881522
Behavioral and developmental effects of prenatal exposure to pentazocine and tripelennamine combinations.	1986-11-01	3808175
Fatal intracranial hemorrhage associated with phenylpropanolamine, pentazocine, and tripelennamine overdose.	1985	4093565
Pentazocine/tripelennamine (T's and blues) abuse: a five year survey of St. Louis, Missouri.	1982-10-01	7166138
Central nervous system complications of addiction to "T's and Blues".	1982-06	7201092
Cholinesterase inhibition by phenothiazine and nonphenothiazine antihistaminics: analysis of its postulated role in synergizing organophosphate toxicity.	1975-02	236606
Pulmonary angiothrombosis caused by "blue velvet" addiction.	1970-11	5476210
An unusual case of antihistamine intoxication.	1967-10	4227701

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Wed Apr 02 07:52:44 GMT 2025` Edited by `admin` on `Wed Apr 02 07:52:44 GMT 2025`
Record UNII	3C5ORO99TY
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TRIPELENNAMINE

Official Name

English

NSC-118946

Preferred Name

English

tripelennamine [INN]

Common Name

English

TRIPELENNAMINE [VANDF]

Common Name

English

Tripelennamine [WHO-DD]

Common Name

English

.BETA.-DIMETHYLAMINOETHYL-2-PYRIDYLAMINOTOLUENE

Systematic Name

English

N,N-DIMETHYL-N'-BENZYL-N'-(.ALPHA.-PYRIDYL)ETHYLENEDIAMINE

Common Name

English

TRIPELENNAMINE [MI]

Common Name

English

TRIPELENNAMINE [HSDB]

Common Name

English

1,2-ETHANEDIAMINE, N,N-DIMETHYL-N'-(PHENYLMETHYL)-N'-2-PYRIDINYL-

Systematic Name

English

N-BENZYL-N',N'-DIMETHYL-N-PYRIDIN-2-YLETHANE-1,2-DIAMINE

Systematic Name

English

N-BENZYL-N',N'-DIMETHYL-N-(2-PYRIDYL)ETHYLENEDIAMINE

Systematic Name

English

2-(BENZYL(2-DIMETHYLAMINOETHYL)AMINO)PYRIDINE

Systematic Name

English

N,N-DIMETHYL-N'-(PHENYLMETHYL)-N'-2-PYRIDINYL-1,2-ETHANEDIAMINE

Systematic Name

English

Classification Tree Code System Code

WHO-ATC

R06AC04