Chemical substance record

Methapyrilene

91-80-5C₁₄H₁₉N₃S261.394 g/mol

Organic/Inorganic Small MoleculeChEBI source record

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. — ChEBI

Safety references

Safety documents & references

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Identity & molecular properties

Source-linked values

CAS number	91-80-5	ChEBI ↗
Molecular formula	C₁₄H₁₉N₃S	ChEBI ↗
Molar mass	261.394 g/mol	ChEBI ↗
Monoisotopic mass	261.12997 Da	ChEBI ↗
Formal charge	0	ChEBI ↗
ChEBI identifier	CHEBI:6820	ChEBI ↗

Cross-source molecular data

PubChem

Molar mass	261.39 g/mol	PubChem ↗
Exact mass	261.12996879 Da	PubChem ↗
Computed XLogP	2.6	PubChem ↗
Topological polar surface area (Å²)	47.6	PubChem ↗
H-bond donors	0	PubChem ↗
H-bond acceptors	4	PubChem ↗
Rotatable bonds	6	PubChem ↗

PubChem computed values are shown separately from the ChEBI record. An exact InChIKey match was used to connect the records. Molecular descriptors do not describe a supplied product’s purity, particle size or performance.

Names & structural identifiers

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Source preferred name

methapyrilene

IUPAC name

N,N-dimethyl-N'-pyridin-2-yl-N'-[(thiophen-2-yl)methyl]ethane-1,2-diamine

InChIKey

HNJJXZKZRAWDPF-UHFFFAOYSA-N

SMILES

CN(C)CCN(Cc1cccs1)c1ccccn1

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

Names & synonyms

HistadylLullaminN,N-dimethyl-N'-pyridin-2-yl-N'-[(thiophen-2-yl)methyl]ethane-1,2-diamineParadormalenePyrathynPyrinistabPyrinistolRest-onRestrylSemikonSleepwellThenylene

Names are supplied by ChEBI. Trade names and related synonyms may describe a broader product context.

Classification & relationships

ChEBI ontology

ethylenediamine derivativeChEBI parent class · 31577 ↗

organic molecular entity

Roles recorded in ChEBI

sedativeH1-receptor antagonistanti-allergic agentcarcinogenic agent

Database role annotations describe reported biological or chemical roles; they are not product approvals or recommendations for use.

Mass ↔ amount of substance

Calculated from sourced mass

Amount

Input unit

Equivalent amount

0.00382564 mol

Uses 261.394 g/mol from ChEBI. Assumes the substance described by this record; no purity or concentration correction is applied.

Elemental composition

Theoretical mass fractions

C

Carbon · 14 atoms

64.33%

N

Nitrogen · 3 atoms

16.08%

S

Sulfur · 1 atom

12.27%

H

Hydrogen · 19 atoms

7.33%

Calculated theoretical mass fractions from the reported formula and PubChem periodic-table atomic masses. These are not assay or purity results.

Research & patent references

Selected source associations

Methapyrilene hepatotoxicity is associated with increased hepatic glutathione, the formation of glucuronide conjugates, and enterohepatic recirculation. ↗Chemico-biological interactions · 2000 Dec 15 · PMID 11137066

The genotoxic potential of methapyrilene using the alkaline Comet assay in vitro and in vivo. ↗Toxicology · 2011 Dec 18 · PMID 22015589

US2581868 · Patent reference ↗Patent cross-reference supplied by ChEBI. Association alone does not establish claim scope.

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Sources & record history

Checked 27 Sep 2026

Identity, formula, mass, synonyms & ontologyEMBL-EBI ChEBI · CHEBI:6820

Release 255, 9 September 2026. ChEBI three-star (manually annotated) source entry. View original record ↗ · CC BY 4.0

Additional molecular descriptorsNCBI PubChem · CID 4098 · retrieved 2026-09-27

PubCAS formats source data, connects references and computes explicitly labelled conversions. CAS cross-references are supplied by ChEBI; they do not constitute CAS verification or endorsement.

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