Product Name

  • Name

    Promethazine hydrochloride

  • EINECS 200-375-2
  • CAS No. 58-33-3
  • Article Data2
  • CAS DataBase
  • Density 1.131 g/cm3
  • Solubility
  • 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;
  • PSA 31.78000
  • LogP 5.10640

Synthetic route

phenergan
58-33-3

phenergan

Promethazine 5-sulfoxide
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;
water
7732-18-5

water

phenergan
58-33-3

phenergan

potassium hexacyanoferrate(III)

potassium hexacyanoferrate(III)

promethazinium ferricyanide monohydrate

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)

sodium hexanitro cobaltate(III)

water
7732-18-5

water

phenergan
58-33-3

phenergan

promethazinium cobaltnitrite monohydrate

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

ammonium tetrathiocyanodiamminochromate(III) monohydrate

phenergan
58-33-3

phenergan

promethazinium reineckate

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%
sodium docusate
577-11-7

sodium docusate

phenergan
58-33-3

phenergan

promethazine docusate
1234189-02-6

promethazine docusate

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

phenergan

10-[2-(dimethylamino)propyl]phenothiazine
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%
phenergan
58-33-3

phenergan

palladium dichloride

palladium dichloride

PdCl3S(C6H4)2NCH2CH(CH3)NH(CH3)2
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%
phenergan
58-33-3

phenergan

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

(4-aldehyde)-promethazine

(4-aldehyde)-promethazine

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

phenergan

zinc(II) chloride
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

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%
yttrium(III) nitrate
13494-98-9

yttrium(III) nitrate

phenergan
58-33-3

phenergan

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

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%
sodium tungstate (VI) dihydrate
10213-10-2

sodium tungstate (VI) dihydrate

phenergan
58-33-3

phenergan

W2O4(C6H4SN(CH2CH(CH3)N(CH3)2)C6H4)2(H2O)2

W2O4(C6H4SN(CH2CH(CH3)N(CH3)2)C6H4)2(H2O)2

Conditions
ConditionsYield
With HCl In water a soln. of Na2WO4*2H2O in distd. H2O was added with stirring to a soln.of PMH in distd. H2O containing few drops of 2 M HCl; the suspn. was set aside for 3 h, filtered, washed (H2O, EtOH), dried in vac. over fused CaCl2; elem. anal.;63%
phenergan
58-33-3

phenergan

cadmium(II) chloride
10108-64-2

cadmium(II) chloride

CdCl(C17H21N2S)2Cl2(1+)*Cl(1-) = [CdCl(C17H21N2S)2Cl2]Cl
182322-85-6

CdCl(C17H21N2S)2Cl2(1+)*Cl(1-) = [CdCl(C17H21N2S)2Cl2]Cl

Conditions
ConditionsYield
In methanol stirring (room temp., 2-3 h); ppt. (concn., cooling), washing, drying, recrystn. (MeOH); elem. anal.;60.1%
phenergan
58-33-3

phenergan

holmium(III) nitrate

holmium(III) nitrate

[Ho(promethazine)2(NO3)2]NO3

[Ho(promethazine)2(NO3)2]NO3

Conditions
ConditionsYield
In water aq. soln. of org. salt added slowly to aq. soln. of Ho nitrate at laboratory temp., ppt. allowed to stand for 1 h; filtered, washed several times with H2O, then with EtOH, dried in vac. over CaCl2; elem. anal.;60%
phenergan
58-33-3

phenergan

cerous nitrate

cerous nitrate

[Ce(promethazine)2(NO3)2]NO3

[Ce(promethazine)2(NO3)2]NO3

Conditions
ConditionsYield
In water aq. soln. of org. salt added slowly to aq. soln. of Ce nitrate at laboratory temp., ppt. allowed to stand for 1 h; filtered, washed several times with H2O, then with EtOH, dried in vac. over CaCl2; elem. anal.;60%
phenergan
58-33-3

phenergan

gadolinium(III) nitrate

gadolinium(III) nitrate

[Gd(promethazine)2(NO3)2]NO3

[Gd(promethazine)2(NO3)2]NO3

Conditions
ConditionsYield
In water aq. soln. of org. salt added slowly to aq. soln. of Gd nitrate at laboratory temp., ppt. allowed to stand for 1 h; filtered, washed several times with H2O, then with EtOH, dried in vac. over CaCl2; elem. anal.;60%
phenergan
58-33-3

phenergan

erbium(III) nitrate

erbium(III) nitrate

[Er(promethazine)2(NO3)2]NO3

[Er(promethazine)2(NO3)2]NO3

Conditions
ConditionsYield
In water aq. soln. of org. salt added slowly to aq. soln. of Er nitrate at laboratory temp., ppt. allowed to stand for 1 h; filtered, washed several times with H2O, then with EtOH, dried in vac. over CaCl2; elem. anal.;60%
phenergan
58-33-3

phenergan

dysprosium nitrate

dysprosium nitrate

[Dy(promethazine)2(NO3)2]NO3

[Dy(promethazine)2(NO3)2]NO3

Conditions
ConditionsYield
In water aq. soln. of org. salt added slowly to aq. soln. of Dy nitrate at laboratory temp., ppt. allowed to stand for 1 h; filtered, washed several times with H2O, then with EtOH, dried in vac. over CaCl2; elem. anal.;60%
phenergan
58-33-3

phenergan

lutetium nitrate

lutetium nitrate

[Lu(promethazine)2(NO3)2]NO3

[Lu(promethazine)2(NO3)2]NO3

Conditions
ConditionsYield
In water aq. soln. of org. salt added slowly to aq. soln. of Lu nitrate at laboratory temp., ppt. allowed to stand for 1 h; filtered, washed several times with H2O, then with EtOH, dried in vac. over CaCl2; elem. anal.;60%
phenergan
58-33-3

phenergan

neodymium(III) nitrate
16454-60-7

neodymium(III) nitrate

[Nd(promethazine)2(NO3)2]NO3

[Nd(promethazine)2(NO3)2]NO3

Conditions
ConditionsYield
In water aq. soln. of org. salt added slowly to aq. soln. of Nd nitrate at laboratory temp., ppt. allowed to stand for 1 h; filtered, washed several times with H2O, then with EtOH, dried in vac. over CaCl2; elem. anal.;60%
phenergan
58-33-3

phenergan

ytterbium(III) nitrate

ytterbium(III) nitrate

[Yb(promethazine)2(NO3)2]NO3

[Yb(promethazine)2(NO3)2]NO3

Conditions
ConditionsYield
In water aq. soln. of org. salt added slowly to aq. soln. of Yb nitrate at laboratory temp., ppt. allowed to stand for 1 h; filtered, washed several times with H2O, then with EtOH, dried in vac. over CaCl2; elem. anal.;60%
phenergan
58-33-3

phenergan

thulium(III) nitrate

thulium(III) nitrate

[Tm(promethazine)2(NO3)2]NO3

[Tm(promethazine)2(NO3)2]NO3

Conditions
ConditionsYield
In water aq. soln. of org. salt added slowly to aq. soln. of Tm nitrate at laboratory temp., ppt. allowed to stand for 1 h; filtered, washed several times with H2O, then with EtOH, dried in vac. over CaCl2; elem. anal.;60%
phenergan
58-33-3

phenergan

terbium(III) nitrate

terbium(III) nitrate

[Tb(promethazine)2(NO3)2]NO3

[Tb(promethazine)2(NO3)2]NO3

Conditions
ConditionsYield
In water aq. soln. of org. salt added slowly to aq. soln. of Tb nitrate at laboratory temp., ppt. allowed to stand for 1 h; filtered, washed several times with H2O, then with EtOH, dried in vac. over CaCl2; elem. anal.;60%
phenergan
58-33-3

phenergan

samarium(III) nitrate

samarium(III) nitrate

[Sm(promethazine)2(NO3)2]NO3

[Sm(promethazine)2(NO3)2]NO3

Conditions
ConditionsYield
In water aq. soln. of org. salt added slowly to aq. soln. of Sm nitrate at laboratory temp., ppt. allowed to stand for 1 h; filtered, washed several times with H2O, then with EtOH, dried in vac. over CaCl2; elem. anal.;60%
europium(III) nitrate

europium(III) nitrate

phenergan
58-33-3

phenergan

[Eu(promethazine)2(NO3)2]NO3

[Eu(promethazine)2(NO3)2]NO3

Conditions
ConditionsYield
In water aq. soln. of org. salt added slowly to aq. soln. of Eu nitrate at laboratory temp., ppt. allowed to stand for 1 h; filtered, washed several times with H2O, then with EtOH, dried in vac. over CaCl2; elem. anal.;60%
phenergan
58-33-3

phenergan

lanthanum(III) nitrate

lanthanum(III) nitrate

[La(promethazine)2(NO3)2]NO3

[La(promethazine)2(NO3)2]NO3

Conditions
ConditionsYield
In water aq. soln. of org. salt added slowly to aq. soln. of La nitrate at laboratory temp., ppt. allowed to stand for 1 h; filtered, washed several times with H2O, then with EtOH, dried in vac. over CaCl2; elem. anal.;60%
phenergan
58-33-3

phenergan

praseodymium(III) nitrate

praseodymium(III) nitrate

[Pr(promethazine)2(NO3)2]NO3

[Pr(promethazine)2(NO3)2]NO3

Conditions
ConditionsYield
In water aq. soln. of org. salt added slowly to aq. soln. of Pr nitrate at laboratory temp., ppt. allowed to stand for 1 h; filtered, washed several times with H2O, then with EtOH, dried in vac. over CaCl2; elem. anal.;60%
uranyl(VI) acetate dihydrate

uranyl(VI) acetate dihydrate

phenergan
58-33-3

phenergan

UO2(CH3CO2)2(C6H4SN(CH2CH(CH3)N(CH3)2)C6H4)(H2O)2

UO2(CH3CO2)2(C6H4SN(CH2CH(CH3)N(CH3)2)C6H4)(H2O)2

Conditions
ConditionsYield
In water soln. refluxed for 6 h; cooling under ice-cold water for 4 d; ppt. filtered and dried in vac.; elem. anal.;50%
palladium(II) nitrate hydrate

palladium(II) nitrate hydrate

phenergan
58-33-3

phenergan

((C6H4)(C6H4)N(CH2CH(CH3)NH(CH3)2)S)2Pd2Cl5(1+)*NO3(1-)=[((C6H4)(C6H4)N(CH2CH(CH3)NH(CH3)2)S)2Pd2Cl5]NO3
191718-60-2

((C6H4)(C6H4)N(CH2CH(CH3)NH(CH3)2)S)2Pd2Cl5(1+)*NO3(1-)=[((C6H4)(C6H4)N(CH2CH(CH3)NH(CH3)2)S)2Pd2Cl5]NO3

Conditions
ConditionsYield
In water slow addn. of aq. soln of ligand to aq. soln. of Pd(NO3)2.xH2O (room temp.), stirring (1 h), cooling (overnight to 4°C); suction filtn., washing (several times, cold water, cold methanol), air drying, drying in vac. over anhydrous CaSO4, recrystn. from hot methanol, elem. anal.;50%
phenergan
58-33-3

phenergan

N-Demethylpromethazine
37707-23-6

N-Demethylpromethazine

Conditions
ConditionsYield
In water (decomposition);
Multi-step reaction with 2 steps
1.1: sodium hydrogencarbonate / water; dichloromethane
2.1: carbonochloridic acid 1-chloro-ethyl ester / 1,2-dichloro-ethane / 43 h / 0 - 115 °C
2.2: 18 h / 75 °C
View Scheme
phenergan
58-33-3

phenergan

Promethiazine sulfoxide hydrochloride
5306-81-0

Promethiazine sulfoxide hydrochloride

Conditions
ConditionsYield
With dihydrogen peroxide In ethanol a) RT, overnight, b) reflux, 2 h;
With n-C4F9; perfluoro-cis-2,3-dialkyloxaziridine; n-C3F7 In various solvent(s) at -40℃; for 0.5h; Yield given;

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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