| Identification | Back Directory | [Name]
ISOTHIPENDYL | [CAS]
482-15-5 | [Synonyms]
Adanton
Odantol
Udantol
Vdantor
Andantol
Andanton
AY 56012
Nilergex
Theruhistin
ISOTHIPENDYL
Isothipendylum
Isothipendyl USP/EP/BP
Dimethylaminoisopropylazaphenothiazine
Isothipendyl (base and/or unspecified salts)
10-(2-Dimethylaminopropyl)-1-Azaphenothiazine
10-(2-dimethylaminopropyl)pyrido(3,2-b)(1,4)benzothiazine
10-(2-Dimethylaminopropyl)-10H-pyrido[3,2-b][1,4]benzothiazine
N,N,α-TriMethyl-10H-pyrido[3,2-b][1,4]benzothiazine-10-ethanaMine
N,N-dimethyl-1-pyrido[3,2-b][1,4]benzothiazin-10-ylpropan-2-amine
10H-Pyrido[3,2-b][1,4]benzothiazine, 10-[2-(dimethylamino)propyl]-
N,N-dimethyl-1-pyrido[3,2-b][1,4]benzothiazin-10-yl-propan-2-amine
10H-Pyrido[3,2-b][1,4]benzothiazine-10-ethanamine, N,N,α-trimethyl-
dimethyl-(1-methyl-2-pyrido[3,2-b][1,4]benzothiazin-10-yl-ethyl)amine
10H-Pyrido[3,2-b][1,4]benzothiazine-10-ethanamine, N,N,alpha-trimethyl-
N,N-Dimethyl-1-(10H-pyrido[3,2-b][1,4]benzothiazin-10-yl)-2-propanamine
10H-Pyrido[3,2-b][1,4]benzothiazine-10-ethanamine, N,N,a-trimethyl- (9CI) | [EINECS(EC#)]
207-578-5 | [Molecular Formula]
C16H19N3S | [MDL Number]
MFCD00865664 | [MOL File]
482-15-5.mol | [Molecular Weight]
285.41 |
| Questions And Answer | Back Directory | [Preparation]
The industrial production method of ISOTHIPENDYL technical grade is carried out according to the following steps: Under nitrogen protection, 100 kg of anhydrous acetonitrile is pumped from an acetonitrile storage tank into a 300 L reactor via a metering pump. 20 kg of 1-hexaazine phenothiazine and 2.4 kg of sodium hydride are added through the feed port. After reacting the materials at 30°C for 1 hour, the steam valve is opened, and steam is introduced into the reactor jacket for reflux reaction for 2 hours. Then, 26.5 kg of 1-p-toluenesulfonyl-2-N,N-dimethylpropylamine is added through the feed port, and the reaction is refluxed for 3 hours. After the materials are cooled to 30°C, insoluble matter is filtered out through a filtration system, and the acetonitrile mother liquor is returned to the reactor from the storage tank. Hydrogen chloride is bubbled into the acetonitrile mother liquor through a vaporizer, buffer tank, and flow meter. White crystals precipitate in the system. HPLC monitoring continues until ISOTHIPENDYL disappears from the mother liquor, at which point the reaction is stopped. The above materials were centrifuged, washed with frozen ethanol, centrifuged again, and dried to obtain 24.1 kg of ISOTHIPENDYL hydrochloride. Acetonitrile was recovered by distillation of the centrifugal mother liquor, and the residual liquid in the reactor was treated and discharged. 70 kg of water was pumped into a 300 L reactor via a metering pump, and the above ISOTHIPENDYL hydrochloride was added through the feed port. The mixture was mechanically stirred until completely dissolved. A 30 wt% NaOH solution was injected into the reactor from a high-level tank via a flow meter. The pH of the system was adjusted to 8, and stirring was continued for 0.5 h before the reaction was stopped. The material was centrifuged and vacuum dried to obtain 20.2 kg of ISOTHIPENDYL with a purity of 99.2% (HPLC) and a yield of 71%. |
| Safety Data | Back Directory | [REACH Registrations]
Active | [Toxicity]
LD50 in mice (mg/kg): 65 ±2 i.p.; 222 ±18 orally (Schlichtegroll) |
| Hazard Information | Back Directory | [Originator]
Theruhistin,Ayerst,US,1957 | [Uses]
Antihistaminic. | [Definition]
ChEBI: Isothipendyl is a tertiary amino compound and an aromatic amine. | [Manufacturing Process]
85 parts of phenylpyridyl amine, 21 parts of powdered sulfur and 1.7 parts of
iodine were heated to 275°C for two hours. Evolution of hydrogen sulfide
began when the mixture reached a temperature of 250°C and became
vigorous when it reached 275°C. Such evolution of hydrogen sulfide
diminished after about one hour at 275°C. A light oil was distilled from the
reaction mixture under vacuum (pressure = 2-3 mm Hg). This oil which
contained phenylpyridyl amine in addition to the thiophenylpyridyl amine was
then treated at boiling temperature with approximately the theoretical amount
of 2-3 normal HCl until complete solution resulted with formation of the HCl
salts of the amines. The solution was then treated with 1 to 2% (based upon
the substance mixture) of active carbon and then filtered hot. The nitrate was
then cooled to 0°C whereupon the thiophenylpyridyl amine hydrochloride
crystallized out while the phenylpyridyl amine hydrochloride remained in
solution. The thiophenylpyridyl amine hydrochloride was filtered off and
suspended in water and the pH adjusted with half concentrated ammonia to 8.
The thiophenylpyridyl amine set free was filtered off and dried. It was in the
form of gold yellow needles and had a melting point of 114°C to 115°C.
40 parts of thiophenylpyridyl amine were dissolved in 200 parts of water free
toluene. After the addition of 16 parts of soda amide, the mixture was
refluxed for 1% hours. Thereafter, 28 parts of dimethylaminoisopropyl chloride
in 30 parts of water free toluene were dropped in and the temperature
maintained at 20°C to 25°C for 30 minutes. Thereafter, the mixture was
heated at 60°C for 30 minutes and subsequently refluxed for 20 minutes.
Water and hydrochloride acid were then added to the reaction mixture and
this mixture rendered alkaline with NaOH and then the alkalized mixture
shaken out with ether. The dimethylaminoisopropyl-N9-thiophenylpyridyl
amine base thus obtained was vacuum distilled. It was then converted to
hydrochloride salt. The monohydrochloride salt is almost white in color and
melts at 213°C to 216°C. The yield was almost 100% of the theoretical. | [Therapeutic Function]
Antihistaminic | [Safety Profile]
A poison by ingestion andintraperitoneal routes. When heated to decomposition itemits toxic vapors of NOx and SOx. |
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