TRIPROLIDINE HYDROCHLORIDE Struktur

Triprolidinhydrochlorid

Bezeichnung:Triprolidinhydrochlorid

CAS-Nr550-70-9

Englisch Name:TRIPROLIDINE HYDROCHLORIDE

CBNumberCB4100461

SummenformelC19H23ClN2

Molgewicht314.85

MOL-Datei550-70-9.mol

Synonyma

Triprolidinhydrochlorid

Triprolidinhydrochlorid physikalisch-chemischer Eigenschaften

Schmelzpunkt	116-118 °C
storage temp.	2-8°C
Löslichkeit	Chloroform (Slightly), Dichloromethane (Slightly), Water (Slightly)
Aggregatzustand	Powder
Wasserlöslichkeit	Soluble to 100 mM in water
Stabilität	Hygroscopic
CAS Datenbank	550-70-9(CAS DataBase Reference)
EPA chemische Informationen	Pyridine, 2-[(1E)-1-(4-methylphenyl)-3-(1-pyrrolidinyl)-1-propenyl]-, monohydrochloride (550-70-9)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	22-36/37/38
S-Sätze:	26-36
RIDADR	3249
WGK Germany	3
RTECS-Nr.	UT7658000
HazardClass	6.1(b)
PackingGroup	III
Toxizität	LD50 oral in rat: 840mg/kg

Gefahreninformationscode (GHS)

TRIPROLIDINE HYDROCHLORIDE Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Originator
Actidil,Burroughs-Wellcome,US,1958
Verwenden
trans-Triprolidine Hydrochloride is a histamine H1 receptor antagonist, which can be used for the prevention of treatment of chronic muscle pain.
Verwenden
Antihistaminic;H1 antagonist
Verwenden
Triprolidine is an antihistaminic agent with anticholinergic properties. Triprolidine is used to treat and prevent symptoms associated with allergies. Triprolidine is also used in combination with cold medicine to provide relief for flu-like symptoms.
Definition
ChEBI: A hydrochloride resulting from the formal reaction of equimolar amounts of triprolidine and hydrogen chloride. Its monohydrate is used for the symptomatic relief of uticaria, rhinitis, and various pruritic skin disorders.
Manufacturing Process
4-Methylacetophenone is first reacted with paraformaldehyde and then with pyrrolidine to give p-methyl-ω-pyrralidinopropiophenone. Atomized lithium (26 g, 3.75 mols) and sodium-dried ether (200 cc) are placed in a 3-liter, 3-necked flask fitted with a Herschberg stirrer, thermometer pocket and a water condenser closed by a calcium chloride tube. A slow stream of dry nitrogen is blown through the flask, which is cooled to - 10°C and n-butyl chloride (138 g, 156 cc, 1.5 mols) is run in with rapid stirring; the mixture is stirred for a further 30 minutes, and then cooled to - 60°C
2-Bromopyridine (193 g, 1.22 mols) is then added dropwise over 20 minutes, the temperature of the reaction mixture being maintained at -50°C. The mixture is stirred for 10 minutes at -50°C and p-methyl-ω- pyrrolidinopropiophenone (112.5 g, 0.5 mol) in dry benzene is then added dropwise over ca 30 minutes, at a temperature of -50°C. The mixture is stirred for a further 2 hours, the temperature being allowed to rise to -30°C but no higher.
The mixture is poured onto excess ice, acidified with concentrated hydrochloric acid, the ether layer separated and extracted with water (1 x 200 cc). The combined aqueous extracts are washed with ether (1 x 200 cc) basified with 0.880 ammonia and extracted with chloroform (3 x 350 cc); the extract is washed with water (2 x 100 cc), dried over sodium sulfate, evaporated, and the residue extracted with boiling light petroleum (BP 60° to 80°C; 10 volumes), filtered hot and evaporated to dryness. The residue is recrystallized from alcohol to give a cream solid (119 g, 80%), MP 117° to 118°C. Recrystallization gives 1-(4-methylphenyl)-1-(2-pyridyl)-3- pyrrolidonopropan-1-ol, MP 119° to 120°C.
1-(4-Methylphenyl)-1-(2-pyridyl)-3-pyrrolidinopropan-1-ol (10.0 g) is heated in a steam bath for 30 minutes with 85% aqueous sulfuric acid (30 cc). The solution is then poured onto crushed ice, excess of ammonia solution added and the liberated oil extracted with light petroleum (BP 60° to 80°C). The extract is dried over anhydrous sodium sulfate and the solvent evaporated to leave an amber syrup (8.8 g) consisting of the cis and trans isomers of 1-(4- methylphenyl)-1-(2-pyridyl)-3-pyrrolidinoprop-1-ene as described in US Patent 2,712,023. The isomers may be separated by base exchange chromatography. The 4-methyl-ω-pyrrolidinopropiophenone required as the starting product for the preparation of the carbinol is prepared by the Mannich reaction (Blicke, Organic Reactions, 1942, vol 1, p 303; Adamson & Billinghurst, Journal of the Chemical Society, 1950,1039) from 4-methylacetophenone and pyrrolidine. The hydrochloride has a MP of 170°C with decomposition.
Trademarks
Actidil (GlaxoSmithKline); Myidyl (USl).
Therapeutic Function
Antihistaminic

TRIPROLIDINE HYDROCHLORIDE Upstream-Materialien And Downstream Produkte

Triprolidinhydrochlorid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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