Name: Promethazine hydrochloride
SKU: 58-33-3

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Basic Information

Molecular Structure:
CAS No.:	58-33-3
Name:	Promethazine hydrochloride
Article Data:	2

Formula:	C₁₇H₂₀N₂S.HCl
Molecular Weight:	320.886
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;
EINECS:	200-375-2
Density:	1.131 g/cm3
Melting Point:	230-232°C
Boiling Point:	403.7 °C at 760 mmHg
Flash Point:	198 °C
Appearance:	white to faint yellow crystalline powder
Hazard Symbols:	Xn
Risk Codes:	22-36/37/38
Safety:	26-36
Transport Information:	UN 2811 6.1/PG 3
PSA:	31.78000
LogP:	5.10640

Synthetic route

: 58-33-3
phenergan

: 7640-51-9
Promethazine 5-sulfoxide

Conditions

Conditions	Yield
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

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

...Expand

: sodium hexanitro cobaltate(III)

: 7732-18-5
water

: 58-33-3
phenergan

: promethazinium cobaltnitrite monohydrate

Conditions

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

...Expand

: ammonium tetrathiocyanodiamminochromate(III) monohydrate

: 58-33-3
phenergan

: promethazinium reineckate

Conditions

Conditions	Yield
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

Conditions	Yield
In water; acetone at 20℃;	99%

: 58-33-3
phenergan

: 60-87-7
10-[2-(dimethylamino)propyl]phenothiazine

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

Downstream Products

60-87-7

37707-23-6

7640-51-9

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Consensus Reports

Reported in EPA TSCA Inventory.

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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Consensus Reports

Specification