4330-99-8

Basic information

• Product Name: Trimeprazine tartrate
• Synonyms: 10-(3-(dimethylamino)-2-methylpropyl)phenothiazinetartrate;10-(3-(dimethylamino)-2-methylpropyl)-phenothiazintartrate(2:1);panectyl;repeltin;temaril;theralene;vallergan;vanectyl
• CAS NO: 4330-99-8
• Molecular Formula: C₄H₆O₆*2C₁₈H₂₂N₂S
• Molecular Weight: 746.98
• EINECS: 224-368-9
• Product Categories: Amines;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 4330-99-8.mol
• Article Data: 1

Chemical Properties

• Melting Point: 153-155°C
• Appearance: /
• Storage Temp.: Refrigerator
• Merck: 14,9704
• CAS DataBase Reference: Trimeprazine tartrate(CAS DataBase Reference)
• NIST Chemistry Reference: Trimeprazine tartrate(4330-99-8)
• EPA Substance Registry System: Trimeprazine tartrate(4330-99-8)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36
• RIDADR: 3249
• WGK Germany: 3
• RTECS: SO6475000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 4330-99-8(Hazardous Substances Data)

Usage

Chemical Properties

White to Off-White Solid

Uses

Antipruritic. Antibacterial, antimicrobial agent

Brand name

Temaril (Allergan).

General Description

Trimeprazine tartrate, (±)10-[3-(dimethylamino)-2-methylpropyl] phenothiazine tartrate(Temaril), occurs as a white to off-white crystalline powderthat is freely soluble in water and soluble in alcohol. Its antihistaminicaction is reported to be from 1.5 to 5 times thatof promethazine. Clinical studies have shown it has a pronouncedantipruritic action that may be unrelated to itshistamine-antagonizing properties.

InChI:InChI=1/2C18H22N2S.C4H6O6/c2*1-14(12-19(2)3)13-20-15-8-4-6-10-17(15)21-18-11-7-5-9-16(18)20;5-1(3(7)8)2(6)4(9)10/h2*4-11,14H,12-13H2,1-3H3;1-2,5-6H,(H,7,8)(H,9,10)/t;;1-,2-/m..0/s1

Synthetic route

cysteamine radical (40055-94-5) + trimeprazine semitartrate (4330-99-8) → 2C18H22N2S*C4H6O6*2H(1+) (1175-88-8, 2015-31-8, 4330-99-8, 14101-45-2, 21287-43-4, 39832-33-2, 66634-41-1)

Conditions	Yield
In water Rate constant; pH 6.5, N2O;

2-hydroxy-ethylsulfanyl (68570-60-5) + trimeprazine semitartrate (4330-99-8) → 2C18H22N2S*C4H6O6*2H(1+) (1175-88-8, 2015-31-8, 4330-99-8, 14101-45-2, 21287-43-4, 39832-33-2, 66634-41-1)

Conditions	Yield
In water Rate constant; pH 6.5, N2O;

2-carboxy-ethylsulfanyl (40055-90-1) + trimeprazine semitartrate (4330-99-8) → 2C18H22N2S*C4H6O6*2H(1+) (1175-88-8, 2015-31-8, 4330-99-8, 14101-45-2, 21287-43-4, 39832-33-2, 66634-41-1)

Conditions	Yield
In water Rate constant; pH 6.5, N2O;

2-amino-2-carboxy-1,1-dimethyl-ethylsulfanyl (15784-30-2) + trimeprazine semitartrate (4330-99-8) → 2C18H22N2S*C4H6O6*2H(1+) (1175-88-8, 2015-31-8, 4330-99-8, 14101-45-2, 21287-43-4, 39832-33-2, 66634-41-1)

Conditions	Yield
In water Rate constant; pH 6.5, N2O;

Cysteine thiyl radical (35772-84-0) + trimeprazine semitartrate (4330-99-8) → 2C18H22N2S*C4H6O6*2H(1+) (1175-88-8, 2015-31-8, 4330-99-8, 14101-45-2, 21287-43-4, 39832-33-2, 66634-41-1)

Conditions	Yield
In water Rate constant; pH 6.5 (phosphate puffer), N2O;

glutathione thiyl radical (40055-99-0) + trimeprazine semitartrate (4330-99-8) → 2C18H22N2S*C4H6O6*2H(1+) (1175-88-8, 2015-31-8, 4330-99-8, 14101-45-2, 21287-43-4, 39832-33-2, 66634-41-1)

Conditions	Yield
In water Rate constant; pH 6.5, N2O;

trimeprazine semitartrate (4330-99-8) + thiyl radical → 2C18H22N2S*C4H6O6*2H(1+) (1175-88-8, 2015-31-8, 4330-99-8, 14101-45-2, 21287-43-4, 39832-33-2, 66634-41-1)

Conditions	Yield
In water pH 6.5;

trimeprazine semitartrate (4330-99-8) → 3H-phenothiazin-3-one

Conditions	Yield
With β‐cyclodextrin In phosphate buffer for 1h; pH=6.8; Kinetics; Further Variations:; pH-values; Reagents; UV-irradiation;

Upstream product

• 4330-99-8 trimeprazine semitartrate 
• 40055-99-0 glutathione thiyl radical 
• 15784-30-2 2-amino-2-carboxy-1,1-dimethyl-ethylsulfanyl 
• 40055-90-1 2-carboxy-ethylsulfanyl 
• 68570-60-5 2-hydroxy-ethylsulfanyl 
• 40055-94-5 cysteamine radical 
• 35772-84-0 Cysteine thiyl radical 

Downstream Products

• 1175-88-8 2C₁₈H₂₂N₂S*C₄H₆O₆*2H⁽¹⁺⁾ 

Relevant articles and documents

Reactions of thiyl radicals with phenothiazines and other antioxidants in aqueous solutions. A pulse radiolysis study.

Reaction rate constants of thiyl radicals with phenothiazines, promethazine (PMZ), chlorpromazine (CPZ), prochlorperazine (PPZ), trimeperazine tarterate (TPZ), and other antioxidants, e. g., ascorbic acid and 2,2-azinobis(3-ethyl benzthiazoline-6 sulphonate) (ABTS) have been estimated using pulse radiolysis technique.In general they are quite high (108-109 M-1 s-1).The k value of cysteine, cysteamine, mercaptoethanol, and mercaptopropionic acid with similar structures and molecular weights are more or less similar for PMZ, CPZ, and PPZ.Rate constants are lower in value for PenS., DT.T, DT.E and GuS. radicals of phenothiazines showing that they are dependent upon the structure and the molecular weight of the compound. Rate constants are the same whether the thiyl radicals are generated from thiols or their corresponding disulphides.The k values for chlorine-containing phenothiazines, chlorpromazine, and prochlorperazine are higher than those of promothazine.