CHEBI:6820 - methapyrilene

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ChEBI Name methapyrilene
Definition A member of the class of ethylenediamine derivatives that is ethylenediamine in which one of the nitrogens is substituted by two methyl groups, and the other nitrogen is substituted by a 2-pyridyl group and a (2-thienyl)methyl group.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C14H19N3S
Net Charge 0
Average Mass 261.38688
Monoisotopic Mass 261.12997
InChI InChI=1S/C14H19N3S/c1-16(2)9-10-17(12-13-6-5-11-18-13)14-7-3-4-8-15-14/h3-8,11H,9-10,12H2,1-2H3
SMILES CN(C)CCN(Cc1cccs1)c1ccccn1
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): carcinogenic agent
A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.
H1-receptor antagonist
H1-receptor antagonists are the drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine.
Application(s): anti-allergic agent
A drug used to treat allergic reactions.
A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.
H1-receptor antagonist
H1-receptor antagonists are the drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine.
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ChEBI Ontology
Outgoing methapyrilene (CHEBI:6820) has role anti-allergic agent (CHEBI:50857)
methapyrilene (CHEBI:6820) has role carcinogenic agent (CHEBI:50903)
methapyrilene (CHEBI:6820) has role H1-receptor antagonist (CHEBI:37955)
methapyrilene (CHEBI:6820) has role sedative (CHEBI:35717)
methapyrilene (CHEBI:6820) is a ethylenediamine derivative (CHEBI:31577)
Incoming methapyrilene hydrochloride (CHEBI:38213) has functional parent methapyrilene (CHEBI:6820)
Synonyms Sources
2-[[2-(dimethylamino)ethyl]-2-thenylamino]pyridine NIST Chemistry WebBook
Histadyl NIST Chemistry WebBook
Lullamin NIST Chemistry WebBook
Methapyrilene KEGG COMPOUND
methypyrilene ChEBI
N,N-dimethyl-N'-pyrid-2-yl-N'-2-thenylethylenediamine ChemIDplus
N,N-dimethyl-N'-pyridin-2-yl-N'-(2-thienylmethyl)ethane-1,2-diamine IUPAC
N-(α-pyridyl)-N-(α-thenyl)-N',N'-dimethylethylenediamine NIST Chemistry WebBook
Pyrathyn ChemIDplus
thenylpyramine ChemIDplus
Brand Names Sources
Histadyl DrugBank
Lullamin DrugBank
Paradormalene DrugBank
Pyrathyn DrugBank
Pyrinistab DrugBank
Pyrinistol DrugBank
Rest-on DrugBank
Restryl DrugBank
Semikon DrugBank
Sleepwell DrugBank
Thenylene DrugBank
Thionylan DrugBank
Manual Xrefs Databases
1738 DrugCentral
DB04819 DrugBank
Methapyrilene Wikipedia
US2581868 Patent
View more database links
Registry Numbers Types Sources
220729 Beilstein Registry Number Beilstein
220729 Reaxys Registry Number Reaxys
91-80-5 CAS Registry Number NIST Chemistry WebBook
91-80-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11137066 PubMed citation Europe PMC
22015589 PubMed citation Europe PMC
24486436 PubMed citation Europe PMC
Last Modified
22 February 2017
General Comment
2011-07-12 An antihistamine and anticholinergic with relatively strong sedative effects, drug products containing methapyrilene were withdrawn from the market in 1979 after being shown to be a potent carcinogen.