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Promethazine hydrochloride
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Name

Promethazine hydrochloride

 EINECS 200-375-2
CAS No. 58-33-3 Density 1.131 g/cm3
PSA 31.78000 LogP 5.10640
Solubility N/A Melting Point 230-232°C
Formula C17H20N2S.HCl Boiling Point 403.7 °C at 760 mmHg
Molecular Weight 320.886 Flash Point 198 °C
Transport Information UN 2811 6.1/PG 3 Appearance white to faint yellow crystalline powder
Safety 26-36 Risk Codes 22-36/37/38
Molecular Structure Molecular Structure of 58-33-3 (Promethazine hydrochloride) Hazard Symbols HarmfulXn
Synonyms

Phenothiazine, 10-[2-(dimethylamino)propyl]-, monohydrochloride (8CI);10-[2-(Dimethylamino)propyl]phenothiazine hydrochloride;Anergan 25;Diprazin;Dorme;Fenazil;Genphen;Himazin;Lergigan;Mepergan;NSC 231688;PhanerganD;Phencen;Phenergan;Phenergan VC;Plletia;Promasun;Prorex;Provigan;Pyrethia;Romergan;

Article Data 2

Promethazine hydrochloride Synthetic route

58-33-3

phenergan

7640-51-9

Promethazine 5-sulfoxide

Conditions
ConditionsYield
With oxygen; cis-nitrous acid at -20℃; citric buffer, pH 3;100%
With hydrogenchloride; potassium iodate; sodium hydroxide In water at 25℃; for 0.166667h; Temperature;
7732-18-5

water

58-33-3

phenergan

potassium hexacyanoferrate(III)

promethazinium ferricyanide monohydrate

Conditions
ConditionsYield
In water E-2 M solns. were mixed; ppt. was filtered, thoroughly washed with distd. water, dried at room temp., elem. anal.;99.5%

sodium hexanitro cobaltate(III)

7732-18-5

water

58-33-3

phenergan

promethazinium cobaltnitrite monohydrate

Conditions
ConditionsYield
In water E-2 M solns. were mixed; ppt. was filtered, thoroughly washed with distd. water, dried at room temp., elem. anal.;99.5%

ammonium tetrathiocyanodiamminochromate(III) monohydrate

58-33-3

phenergan

promethazinium reineckate

Conditions
ConditionsYield
In water E-2 M solns. were mixed; ppt. was filtered, thoroughly washed with distd. water, dried at room temp., elem. anal.;99.5%
577-11-7

sodium docusate

58-33-3

phenergan

1234189-02-6

promethazine docusate

Conditions
ConditionsYield
In water; acetone at 20℃;99%
58-33-3

phenergan

60-87-7

10-[2-(dimethylamino)propyl]phenothiazine

Conditions
ConditionsYield
With sodium hydrogencarbonate In dichloromethane; water Reagent/catalyst;96%
With sodium hydroxide In diethyl ether Purification / work up;90%
58-33-3

phenergan

palladium dichloride

75234-55-8, 76317-76-5

PdCl3S(C6H4)2NCH2CH(CH3)NH(CH3)2

Conditions
ConditionsYield
In hydrogenchloride; water stirring (ambient temp., 1 h); pptn. on cooling (4°C), washing (water, MeOH), drying (vac.), recrystn. (MeOH); elem. anal.;88.5%
58-33-3

phenergan

68-12-2, 33513-42-7

N,N-dimethyl-formamide

(4-aldehyde)-promethazine

Conditions
ConditionsYield
With trichlorophosphate at 0 - 90℃; for 46h; Vilsmeier Reaction; Inert atmosphere;88%
58-33-3

phenergan

7646-85-7

zinc(II) chloride

Zn(C6H4SN(CH2CH(CH3)NH(CH3)2)C6H4)2Cl(3+)*3Cl(1-)=[Zn(C6H4SN(CH2CH(CH3)NH(CH3)2)C6H4)2Cl]Cl3

Conditions
ConditionsYield
In methanol slow addn. of soln. of ZnCl2 to soln. of ligand (room temp.), stirring (1 h), conctg. (reduced pressure), storing (overnight at 4°C); decanting viscous liq., redissolving in methanol with stirring at 60°C, suction filtn., washing (2-3 times, cold methanol), drying (air),drying (vac.), recrystn. (hot methanol), elem. anal.;76.8%
13494-98-9

yttrium(III) nitrate

58-33-3

phenergan

Y(3+)*2C17H20N2S*3NO3(1-) = [Y(C17H20N2S)2(NO3)2](NO3)

Conditions
ConditionsYield
In ethanol refluxing (2 h); pptn. on cooling, washing (EtOH), drying (vac.); elem. anal.;70%

Promethazine hydrochloride Consensus Reports

Reported in EPA TSCA Inventory.

Promethazine hydrochloride Specification

The IUPAC name of Promethazine hydrochloride is N,N-dimethyl-1-phenothiazin-10-ylpropan-2-amine hydrochloride . With the CAS registry number 58-33-3, it is also named as (+-)-10-(2-(Dimethylamino)propyl)phenothiazine monohydrochloride; Allerfen; Eusedon Mono; Mymethazine Fortis; Phenothiazine, 10-(2-(dimethylamino)propyl)-, monohydrochloride; PMS Promethazine. The product's categories are active pharmaceutical ingredients, intermediates & fine chemicals, pharmaceuticals, sulfur & selenium compounds and histamine receptor.

The Promethazine hydrochloride is white to faint yellow crystalline powder with bitter taste. It can oxidize slowly in air, acquiring a blue color. In addition, it is incompatible with alkalis and alkaline solutions such as those of aminophylline, soluble barbiturates and phenytoin sodium. Iron(III) and copper(III) accelerate the degradation. The Promethazine hydrochloride must be kept in a sealed container which is placed in a cool, well-ventilated area. It can be used as antihistaminic, antiemetic and CNS depressant. 

The Promethazine hydrochloride is harmful if swallowed. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 4.78; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.87; (4)ACD/LogD (pH 7.4): 3.3; (5)ACD/BCF (pH 5.5): 3.07; (6)ACD/BCF (pH 7.4): 83.45; (7)ACD/KOC (pH 5.5): 11.53; (8)ACD/KOC (pH 7.4): 313.03; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Enthalpy of Vaporization: 65.51 kJ/mol; (13)Vapour Pressure: 9.96E-07 mmHg at 25°C; (14)Rotatable Bond Count: 3; (15)Exact Mass: 320.111397; (16)MonoIsotopic Mass: 320.111397; (17)Topological Polar Surface Area: 31.8; (18)Heavy Atom Count: 21; (19)Complexity: 298.

People can use the following data to convert to the molecule structure. SMILES: Cl.S2c1ccccc1N(c3c2cccc3)CC(N(C)C)C; InChI: InChI=1/C17H20N2S.ClH/c1-13(18(2)3)12-19-14-8-4-6-10-16(14)20-17-11-7-5-9-15(17)19;/h4-11,13H,12H2,1-3H3;1H. Promethazine hydrochloride has many suppliers, such as Ningbo Hi-Tech Biochemicals Co., Ltd., Changzhou Ilhang Fine Chemical Co., Ltd. and Hubei Hengshuo Chemical Co., Ltd..

The following is the toxicity data which has been tested. 

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 20mg/kg (20mg/kg) BEHAVIORAL: EXCITEMENT

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: STIFFNESS		 Lancet. Vol. 1, Pg. 368, 1980.
dog LD50 subcutaneous 250mg/kg (250mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 54, Pg. 688, 1958.
guinea pig LD50 intraperitoneal 35mg/kg (35mg/kg)   Pharmazie. Vol. 38, Pg. 749, 1983.
guinea pig LD50 intravenous 42500ug/kg (42.5mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 113, Pg. 313, 1958.
human TDLo oral 3500ug/kg/D (3.5mg/kg) BEHAVIORAL: SLEEP

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: REGIDITY		 American Journal of Psychiatry. Vol. 113, Pg. 654, 1957.
 
mouse LD50 intraperitoneal 160mg/kg (160mg/kg)   Cesko-Slovenska Farmacie. Vol. 15, Pg. 526, 1966.
mouse LD50 intravenous 50mg/kg (50mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 108, Pg. 340, 1953.
mouse LD50 oral 255mg/kg (255mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES		 Archives Internationales de Pharmacodynamie et de Therapie. Vol. 135, Pg. 364, 1962.
 
mouse LD50 subcutaneous 240mg/kg (240mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 22, Pg. 375, 1980.
rat LD50 intraperitoneal 170mg/kg (170mg/kg)   Cesko-Slovenska Farmacie. Vol. 15, Pg. 526, 1966.
rat LD50 intravenous 15mg/kg (15mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 22, Pg. 375, 1980.
rat LD50 subcutaneous 400mg/kg (400mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 22, Pg. 375, 1980.

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