| Identification | Back Directory | [Name]
METHAPYRILENE | [CAS]
91-80-5 | [Synonyms]
a3322
AH-42
A 3322
histase
Lulamin
Rest-On
Restryl
Semikon
Tenalin
Lullamin
Histadyl
Pyrathyn
Thenylene
Sleepwell
Thionylan
nci-c09018
NCI-C55550
Pyrinistab
Pyrinistol
pyrahistine
tenalinbase
histadylbase
Metapyrilene
methapyrilene
Paradormalene
Methapyriline
thenylenebase
Thenylpyramine
methylpyrilene
Methaphenilene
rcrawastenumberu155
methapyrilene,(base)
Rcra waste number U155
2-[(2-dimethyl-aminoethyl)-2-thenylamino]pyridine
2-[[2-(Dimethylamino)ethyl]-2-thenylamino]pyridine
2-((2-(dimethylamino)ethyl)-2-thenylamino)-pyridin
2-((2-(dimethylamino)ethyl)-2-thenylamino)pyridine
N,N-dimethyl-N-2-pyridyl-N-2-thenylethylenediamine
2-((2-(dimethylamino)ethyl)-2-thienylamino)pyridine
Pyridine, 2-[[2-(dimethylamino)ethyl]-2-thenylamino]-
n,n-dimethyl-n’-pyrid-2-yl-n’-2-thenylethylenediamine
N,N-Dimethyl-N'-pyrid-2-yl-N'-2-thenylethylenediamine
2-dimethylaminoethyl-(2-pyridyl)-(2-thienylmethyl)amine
N-(2-Pyridyl)-N-(2-thienylmethyl)-N',N'-dimethylethylenediamine
n,n-dimethyl-n’-2-pyridinyl-n’-(2-thienylmethyl)-2-ethanediamine
N-(alpha-Pyridyl)-N-(alpha-thenyl)-N',N'-dimethylethylenediamine
n-(alpha-pyridyl)-n-(alpha-thenyl)-n’,n’-dimethylethylenediamine
n,n-dimethyl-n’-2-pyridinyl-n’-(2-thienylmethyl)-1,2-ethanediamide
n,n-dimethyl-n’-2-pyridinyl-n’-(2-thienylmethyl)-1,2-ethanediamine
N,N-Dimethyl-N'-2-pyridinyl-N'-(2-thienylmethyl)-1,2-ethanediamine
1,2-Ethanediamine, N,N-dimethyl-N'-2-pyridinyl-N'-(2-thienylmethyl)-
N',N'-dimethyl-N-pyridin-2-yl-N-(thiophen-2-ylmethyl)ethane-1,2-diamine | [EINECS(EC#)]
202-099-8 | [Molecular Formula]
C14H19N3S | [MDL Number]
MFCD00242573 | [MOL File]
91-80-5.mol | [Molecular Weight]
261.386 |
| Chemical Properties | Back Directory | [Appearance]
colourless liquid | [Melting point ]
25°C | [Boiling point ]
bp0.45 125-135°; bp3 173-175° | [density ]
1.1388 (rough estimate) | [refractive index ]
nD25 1.5842 (also reported as 1.5835) | [storage temp. ]
Refrigerator, under inert atmosphere | [solubility ]
DMSO (Sparingly), Methanol (Slightly) | [form ]
Oil | [pka]
pKa 3.02 ± 0.05;8.24± 0.11(H2O,t undefined,I=0.30(NaCl)) (Uncertain) | [color ]
Colourless to Light Yellow | [Stability:]
Stable. Incompatible with strong oxidizing agents. | [Water Solubility ]
601.2mg/L(30 ºC) | [EPA Substance Registry System]
Methapyrilene (91-80-5) |
| Hazard Information | Back Directory | [Chemical Properties]
colourless liquid | [Uses]
antihypertensive, AT1 angiotensin II antagonist | [Definition]
ChEBI: 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. | [General Description]
Clear colorless liquid. | [Reactivity Profile]
An amine, organosulfide. Organosulfides are incompatible with acids, diazo and azo compounds, halocarbons, isocyanates, aldehydes, alkali metals, nitrides, hydrides, and other strong reducing agents. Reactions with these materials generate heat and in many cases hydrogen gas. Many of these compounds may liberate hydrogen sulfide upon decomposition or reaction with an acid. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides. | [Health Hazard]
ACUTE/CHRONIC HAZARDS: METHAPYRILENE is highly toxic by ingestion. | [Fire Hazard]
Flash point data for METHAPYRILENE are not available, but METHAPYRILENE is probably combustible. | [Originator]
Thenylene ,Abbott,US,1947 | [Manufacturing Process]
To a slurry of sodamide in 200 cc of toluene representing 6.7 g of sodium was added at 30° to 40°C, 32.3 g (0.31 mol) of 2-aminopyridine. The mixture was heated to reflux temperature and was refluxed for 1? hours. To the resulting mixture was added over a period of approximately one hour a solution of 32 g of freshly distilled N,N-dimethyl-β-chloroethylamine in 40 to 50 cc of dry toluene, The reaction mixture was then heated for 2 hours at reflux temperature. Thereafter, 200 cc of water was added and the toluene layer was separated and washed with water. The toluene was stripped from the mixture by distillation and the residue was distilled under reduced pressure. The distillate was refractionated and the portion distilled at 93° to 103°C/1 mm was recovered. Yield of N-(2-pyridyl)-N',N'-dimethyl-ethylenediamine, 60%.
A solution of 20 g (0.121 mol) of N-(2-pyridyl)-N',N'-dimethylethylenediamine in 25 cc of toluene was added to a slurry of sodamide in 100 cc of toluene representing 2.8 g of sodium. The mixture was refluxed for one hour. To this mixture was added over a period of ? hour a solution of 16 g (0.121 mol) of 2-thenyl chloride in 25 cc of toluene. The resulting reaction mixture was refluxed for 3 hours. Thereafter, water was added and the toluene layer was separated and washed with water.
The toluene was then stripped off by distillation and the residue was distilled under reduced pressure. The main fraction was redistilled. Yield of N-(2- pyridyl)-N-(2-thenyl)-N',N'-dimethyl-ethylenediamine was 69%; BP 130° to 140°C/0.4 mm. A portion of the product was dissolved in ether and an ether solution of hydrogen chloride was added. The monohydrochloride of N-(2- pyridyl)-N-(2-thenyl)-N',N'-dimethyl-ethylenediamine which separated was washed with ether and dried. | [Brand name]
3p pane;Brexin;Conac;Dexapirilene;Dormin;Duohist;Duo-tussin;Dylhista;Histadyl ec;Hitalones;Isopap;Lallamin;Lullamin;M.p.;Methistaline;Methril spansul;M-p;Myci-spray;Norane;Paradormalene;Peral;Placitabs;Pyrathyn;Pyrinistab;Pyrinistol;Rejam;Thenylene;Thionylan;W83. | [Therapeutic Function]
Antihistaminic | [World Health Organization (WHO)]
Methapyrilene, an antihistamine with moderate sedative activity,
was introduced in 1947 for the treatment of various allergic conditions and was
subsequently incorporated in many over-the-counter sleeping aids. In the early
1970s it was identified as a carcinogen in rats and, although there was no direct
evidence that it constitutes a health hazard to man, it was withdrawn in many
countries.
(Reference: (WHODI) WHO Drug Information, 2, 4, 1979) | [Synthesis]
Methapyrilene is synthesized by heating a
2-thienyl halide with an alkali metal salt
of N,N-dimethyl-N_x0002_-(2-pyridinyl)-1,2-ethanediamine
. | [Metabolic pathway]
When methaphenilene is
incubated with rat liver microsomes, it is metabolized via N-oxide formation and
N-dealkylation which includes removal of the
dimethylamino moiety, the thiophenylmethyl moiety of
methaphenilene, and the benzyl moiety of
pyribenzamine. |
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