Basic information
- CAS
91-80-5- Standard SMILES
CN(C)CCN(Cc1cccs1)c1ccccn1- InChIKey
HNJJXZKZRAWDPF-UHFFFAOYSA-N- Molecular formula
- C14H19N3S
- Average molar mass
- 261.39 g/mol
- Monoisotopic mass
- 261.12996861
Overview
Methapyrilene is a clear colorless liquid. (NTP, 1992)
Names & identifiers
- Preferred name
- Methapyrilene
- IUPAC
- N,N-dimethyl-N'-pyridin-2-yl-N'-(thiophen-2-ylmethyl)ethane-1,2-diamine
- English name
- Methapyrilene
- Molecular formula
- C14H19N3S
- Molecular weight
- 261.38576
Names & synonyms
methapyrilene91-80-5ThenylpyraminePyrinistolThionylanRestrylMetapyrileneSleepwellSemikonParadormaleneLullaminPyrathyn
Show more names
Methaphenilenea3322AH-42A 3322histase
PyrinistabThenyleneTenalinRest-onHistadrylLulaminmethypyrileneMetapirileno
Database identifiers
- CAS
91-80-5- PubChem CID
- 4098
- DTXSID
DTXSID2023278- ChEMBL
CHEMBL1411979- ChEBI
CHEBI:6820- UNII
- A01LX40298
- EC Number
- 202-099-8
- Nikkaji
- J4.348F
Properties
Computed structural properties
- XLogP
- 2.6
- Topological polar surface area
- 47.6 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 6
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 235
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LogP2.87
Color/FormLIQUID
SolubilityWHITE CRYSTALLINE POWDER; USUALLY FAINT ODOR; SOL IN WATER & ALCOHOL; PH (1 IN 20 SOLN) BETWEEN 3 & 4. /METHAPYRILENE FUMARATE/
Human DrugsPharmaceuticals
Boiling Point
343 to 347 °F at 3 mmHg (NTP, 1992)
173-175 °C at 3.00E+00 mm Hg
173-175 °C @ 3 MM HG
BP: 125-135 °C @ 0.45 MM HG
Melting PointMP: 135-136 °C. /METHAPYRILENE FUMARATE/
Vapor Pressure7.0X10-4 mm Hg at 25 °C (extrapolated from vapor pressure data at higher temperatures, SRC)
Refractive Index
INDEX OF REFRACTION: 1.5915 @ 20 °C/D; MAX ABSORPTION (WATER): 238 NM (LOG E= 4.17), 304 NM (LOG E= 3.60)
INDEX OF REFRACTION: 1.5842 @ 25 °C/D, 1.5835 @ 25 °C/D
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information1,2-Ethanediamine, N,N-dimethyl-N'-2-pyridinyl-N'-(2-thienylmethyl)-: Does not have an individual approval but may be used under an appropriate group standard
DOT LabelPoison
Fire HazardsFlash point data for this chemical are not available, but it is probably combustible. (NTP, 1992)
Health HazardsACUTE/CHRONIC HAZARDS: This material is highly toxic by ingestion. (NTP, 1992)
Hazards Summary
The major hazards encountered in the use and handling of methapyrilene stem from its toxicologic properties. Primarily toxic by ingestion, exposure to this liquid may occur from its production or veterinary use (parenteral or topical application) on domestic animals to treat histamine associated allergies or hypersensitivities. Effects from exposure may include tachycardia, CNS depression, hallucinations, toxic psychosis, cerebral edema, deep coma, cardio-respiratory collapse, or death.
Reactive GroupAmines, Phosphines, and Pyridines
Special ReportsLijinsky W; Chronic Toxicity Tests of Pyrilamine Maleate and Methapyrilene Hydrochloride in F344 rats; Food and Chemical Toxicology 22 (1): 27-30 (1984).
Chemistry & industry
Pharmacology
ATC Code
R - Respiratory system
QR - Respiratory system
Mechanism of ActionVERY LITTLE IS KNOWN ABOUT MODE OF CNS ACTION OF THESE NONPRESCRIPTION DRUGS. IT HAS BEEN SUGGESTED THAT CENTRAL ANTIMUSCARINIC ACTION IS COMMON TO ALL. /NONPRESCRIPTION SEDATIVE-HYPNOTIC DRUGS/
Metabolism/Metabolites
The metabolism of methapyrilene, was examined in vivo by glc and glc-mass spectrometric analysis of rat urinary extracts. Dosing the animals with tetradeuterium labeled methapyrilene helped identify 7 different metabolites of methapyrilene in the urine, including (5-hydroxylpyridyl)-methapyrilene, which was identified by comparison with a synthetic reference standard. After 4 weeks of treatment with methapyrilene, rats also excrete detectable amounts of the 3- and (6-hydroxylpyridyl)-methapyrilene metabolites suggesting that pretreatment with methapyrilene alters the metabolism of the pyridine ring. Metabolic removal of the 2-thienylmethylene moiety is also facile, as large amounts of N'-(2-pyridyl)-N,N-dimethylethylenediamine and its metabolite N'-(2(5-hydroxylpyridyl))-N,N-dimethylethylenediamine are excreted under all dosing regimens. Urinary concn of both methapyrilene and metabolites decline with time, despite continuous dosing, indicating a change in absorption, metabolism, and/or excretion of methapyrilene on repeated dosing.
Rats were fed 100 or 1000 ppm methapyrilene in their diet for 1, 2, 4, 8 or 16 weeks. Liver microsomes were prepared from both control and treated rats. After incubation with 1 mM methapyrilene, eight metabolites were detected and six were quantitated. Five of the metabolites have been previously identified as 2-hydroxymethyl-thiophene, thiophene-2-carboxylic acid, N-(2-thienylmethyl)-2-aminopyridine, N-2-pyridyl-N'N'-dimethylethylenediamine, and 2-aminopyridine. Three other metabolites have been tentatively identified based on their mass spectral fragmentation patterns as normethapyrilene, (5-hydroxypyridyl)methapyrilene, and methapyrileneamide. The same metabolites were found in both control and treated animals, the most abundant being normethapyrilene and N-2-pyridyl-N'N'-dimethylenethylenediamine. Pretreatment with methapyrilene resulted in inhibition of both consumption of methapyrilene and formation of some metabolites. However increases in the formation of all of the metabolites also occurred under different treatment conditions. In both control and treated tissue, the preliminary mass balance was less than 55%, except in incubations with tissue from rats treated with 1000 ppm for 8 or 16 weeks where it was 92 and 89%, respectively. Dramatic increases in the fraction of N-(2-thienylmethyl)-2-aminopyridine, methapyrileneamide, normethapyrilene and (5-hydroxypyridyl)methapyrilene relative to methapyrilene consumed account for the increase in the mass balance after 8 weeks pretreatment with 1000 ppm methapyrilene, and increases in the amounts of N-2-pyridyl-N'N'-dimethylenediamine, (5-hydroxypyridyl)methapyrilene and thiophene-2-carboxylic acid account for the higher mass balance after 16 weeks.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…