You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:36 UTC
HMDB IDHMDB0014930
Secondary Accession Numbers
  • HMDB14930
Metabolite Identification
Common NameTripelennamine
DescriptionTripelennamine, also known as PBZ-SR or azaron, belongs to the class of organic compounds known as 2-benzylaminopyridines. These are aromatic compounds containing pyridine ring substituted at the 2-position by a benzylamine group. Tripelennamine acts primarily as an antihistamine, or H1 receptor antagonist. In addition to its antihistamine properties, tripelennamine also acts as a weak serotonin-norepinephrine-dopamine reuptake inhibitor (SNDRI). Tripelennamine is a drug. Tripelennamine is mildly sedating. Tripelennamine is a very strong basic compound (based on its pKa). In humans, tripelennamine is involved in tripelennamine h1-antihistamine action. Other side effects can include irritation, dry mouth, nausea, and dizziness. The drug was patented at CIBA, which merged with Geigy into Ciba-Geigy, and eventually becoming Novartis. Tripelennamine, sold under the brand name Pyribenzamine by Novartis, is a drug that is used as an antipruritic and first-generation antihistamine. One example is the line of Pyribenzamine Cough Syrups which contains codeine and with and without decongestants listed in the 1978 Physicians' Desk Reference; the codeine-tripelennamine synergy is well-known and does make such mixtures more useful for their intended purposes. Tripelennamine was first synthesized in 1946 by Carl Djerassi, working in the laboratory of Charles Huttrer at CIBA, shortly after Djerassi got his B.S. It was his first patent. Where and when it is/was in common use, tripelennamine is used much like other mildly-anticholinergic antihistamines for treating conditions of the upper respiratory tract arising from illnesses and hay fever. It can be used alone or in combination with other agents to have the desired effect. It has little to no anticholinergic activity.
Structure
Data?1582753236
Synonyms
ValueSource
PBZ-SRHMDB
PBZHMDB
AzaronHMDB
Tripelennamine citrateHMDB
Tripelennamine maleateHMDB
Tripelennamine maleate (1:1)HMDB
Tripelennamine monohydrochlorideHMDB
Asid bonz brand OF tripelennamine hydrochlorideHMDB
Parnell brand OF tripelennamine hydrochlorideHMDB
HistantinHMDB
Chefaro brand OF tripelennamineHMDB
PyribenzamineHMDB
Tripelennamine citrate (1:1)HMDB
Tripelennamine hydrochlorideHMDB
VetibenzaminHMDB
Chemical FormulaC16H21N3
Average Molecular Weight255.358
Monoisotopic Molecular Weight255.173547687
IUPAC NameN-benzyl-N-[2-(dimethylamino)ethyl]pyridin-2-amine
Traditional Nametripelennamine
CAS Registry Number91-81-6
SMILES
CN(C)CCN(CC1=CC=CC=C1)C1=CC=CC=N1
InChI Identifier
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
InChI KeyUFLGIAIHIAPJJC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2-benzylaminopyridines. These are aromatic compounds containing pyridine ring substituted at the 2-position by a benzylamine group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzylamines
Direct Parent2-benzylaminopyridines
Alternative Parents
Substituents
  • 2-benzylaminopyridine
  • Dialkylarylamine
  • Aminopyridine
  • Pyridine
  • Imidolactam
  • Heteroaromatic compound
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organonitrogen compound
  • Amine
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.84 g/LNot Available
LogP3.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.84 g/LALOGPS
logP3.05ALOGPS
logP3.2ChemAxon
logS-2ALOGPS
pKa (Strongest Basic)8.76ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area19.37 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity81.27 m³·mol⁻¹ChemAxon
Polarizability29.86 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0a4i-0090000000-c34cc7c068c800fe56be2017-09-12View Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0a4i-0090000000-c34cc7c068c800fe56be2018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-9200000000-0d2486042b7353578cae2017-09-01View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4l-9200000000-0d2486042b7353578cae2021-09-05View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0bt9-0090000000-334f534255262b94521e2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0090000000-11e8826e02efb97b98c92017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00kf-8930000000-1b7607b1d6869ef01c342017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00kf-9500000000-e76eabb3bb757d44acfa2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00kf-9400000000-e99107bbb2260bd80b262017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-0290000000-1cb8a1736406d25862662017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-4090000000-63473fef524306c783802016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-022c-9240000000-25e1df027e0be085969b2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-33a105923d92b87de1ff2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0490000000-0256a416c1400912ea412016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0il0-1930000000-7b176551463e8116cd4a2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mo-8900000000-3d9f90a28663006a5cba2016-08-03View Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00792 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00792 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00792
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5385
KEGG Compound IDC07180
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTripelennamine
METLIN IDNot Available
PubChem Compound5587
PDB IDNot Available
ChEBI ID331013
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Hamelin BA, Bouayad A, Drolet B, Gravel A, Turgeon J: In vitro characterization of cytochrome P450 2D6 inhibition by classic histamine H1 receptor antagonists. Drug Metab Dispos. 1998 Jun;26(6):536-9. [PubMed:9616188 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
Gene Name:
HRH1
Uniprot ID:
P35367
Molecular weight:
55783.6
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Shimizu K, Nakajyo S, Urakawa N: [Drug sensitivity of the isolated stomach and ileal preparation from a vole]. Nihon Heikatsukin Gakkai Zasshi. 1982 May;18(2):93-103. [PubMed:6759742 ]
  3. Chiba S: Blocking effect of tripelennamine on histamine--induced positive chronotropic and inotropic responses of the dog atrium. Tohoku J Exp Med. 1976 Nov;120(3):299-300. [PubMed:996853 ]
  4. Sansone M: Antihistaminic-opioid combination: effect on locomotor activity in mice. Pol J Pharmacol Pharm. 1988 Sep-Oct;40(5):515-23. [PubMed:3253717 ]
  5. Ohta Y, Kobayashi T, Ishiguro I: Role of endogenous serotonin and histamine in the pathogenesis of gastric mucosal lesions in unanaesthetised rats with a single treatment of compound 48/80, a mast cell degranulator. Pharmacol Res. 1999 Apr;39(4):261-7. [PubMed:10208755 ]
  6. Suzuki T, Mori T, Tsuji M, Misawa M, Onodera K: Interactions between H1-antagonists and opioids: a drug discrimination study. Psychopharmacology (Berl). 1997 Jun;131(4):346-53. [PubMed:9226736 ]