84-96-8

Basic information

• Product Name: Trimeprazine
• Synonyms: n,n,2-trimethyl-3-phenothiazin-10-yl-propan-1-amine;TRIMEPRAZINE;alimemazine;10-[2-Methyl-3-(dimethylamino)propyl]phenothiazine;10-[3-(Dimethylamino)-2-methylpropyl]phenothiazine;10H-Phenothiazine-10-propanamine, N,N,beta-trimethyl-;Alimezine;Bayer 1219
• CAS NO: 84-96-8
• Molecular Formula: C₁₈H₂₂N₂S
• Molecular Weight: 298.45
• EINECS: 201-577-3
• Product Categories: TEMARIL
• Mol File: 84-96-8.mol

Chemical Properties

• Melting Point: 68°C
• Boiling Point: bp0.3 150-175°
• Flash Point: 208°C
• Appearance: /
• Density: 1.1163 (rough estimate)
• Refractive Index: 1.6000 (estimate)
• PKA: pKa 9.00 (Uncertain)
• Water Solubility: 0.942 mg/L
• CAS DataBase Reference: Trimeprazine(CAS DataBase Reference)
• NIST Chemistry Reference: Trimeprazine(84-96-8)
• EPA Substance Registry System: Trimeprazine(84-96-8)

Safety Data

• Hazardous Substances Data: 84-96-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Trimeprazine is used as an antihistamine for treating itching during dermatitis of both allergic and nonallergic origin. It works by blocking the H1 receptor, reducing the allergic response and providing relief from itching and other symptoms associated with dermatitis.
Additionally, Trimeprazine is used for its sedative properties, making it useful in treating insomnia and anxiety disorders. Its weak anticholinergic effects can also be beneficial in managing certain gastrointestinal conditions, such as nausea and vomiting.

Originator

Temaril,SKF,US,1958

Manufacturing Process

95% sodamide (2.77 grams) is added to a solution of phenthiazine (9.6 grams) in xylene (140 cc) at a temperature of 130°C and the mixture is heated with reflux for 2 hours. A 0.61 N solution (90 cc) of 1-chloro-2-methyl-3-dimethylaminopropane in xylene is then added over 50 minutes and heating with reflux is continued for 20 hours. After cooling, the mixture is treated with water (40 cc) and N methanesulfonic acid (70 cc). The aqueous layer is washed with ether, treated with aqueous sodium hydroxide (density = 1.33; 10 cc) and extracted with ether. The extract is dried over potassium carbonate and evaporated and the residue is distilled in vacuo. 3-(10-phenthiazinyl)-2-methyl-1-dimethylaminopropane (12.6 grams) is collected, distilling between 150° and 175°C under a pressure of about 0.3 mm Hg. By dissolving this base in acetone and adding ethereal hydrogen chloride, a hydrochloride is obtained, MP 216° to 217°C.

InChI:InChI=1/C18H22N2S/c1-14(12-19(2)3)13-20-15-8-4-6-10-17(15)21-18-11-7-5-9-16(18)20/h4-11,14H,12-13H2,1-3H3

Upstream product

• 50-00-0 formaldehyd 
• 92-84-2 10H-phenothiazine 
• 23349-86-2 3-(dimethylamino)-2-methylpropylchloride 
• 124-40-3 dimethyl amine 
• 20962-92-9 10-allylphenothiazine 
• 201230-82-2 carbon monoxide 

Downstream Products

• 84-96-8 10-3-(dimethylamino-2-methylpropyl)phenothiazine cation 
• 50-00-0 formaldehyd 

Relevant articles and documents

Isobutazine specific impurity as well as analysis method and removal method thereof

The invention discloses an isobutazine specific impurity as well as an analysis method and a removal method thereof. According to the analysis method, the specific impurity Tt-2 can be effectively detected through combination of high performance liquid chromatography and an ultraviolet detector, and the impurity cannot be detected through previous EP and USP methods. According to the removal method, the specific impurity Tt-2 can be effectively removed, other process impurities can also be removed, the purity and character of the product are further improved, and the removal method has great significance in subsequent research and development of the product.

One-pot synthesis of pharmacologically active diamines via rhodium- catalysed carbonylative hydroaminomethylation of heterocyclic allylic amines

Pharmacologically active derivatives of phenothiazine, iminodibenzyl, carbazole and pyrazole are prepared with high yields and chemoselectivity by the reaction of the corresponding N-allylic or N-methallylic compounds, primary or secondary amines, carbon monoxide and hydrogen in the presence of [Rh(cod)Cl]2 as catalyst via a one pot hydroformylation - amine condensation - reduction sequence.

Endor Studies of Cation Radicals from Pharmacologically Active Phenothiazines

A variety of substituted phenothiazine cation radicals, including those from pharmacologically active derivatives, e.g. chloropromazine, alimemazine and laevomepromazine, have been studied by means of ENDOR and TRIPLE resonace spectroscopy.These techniques allowed accurate determinations of hyperfine coupling constants, including their signs.Conclusions concerning molecular structure (e.g. twist angles) could be drawn, supporting previous investigations of the interrelationship of molecular conformations with the pharmacological potential, i.e. neuroleptic, antihistaminic or anti-Parkinsonian.