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Promethazine hydrochloride structure
Promethazine hydrochloride structure

Promethazine hydrochloride

Iupac Name:N,N-dimethyl-1-phenothiazin-10-ylpropan-2-amine;hydrochloride
CAS No.: 58-33-3
Molecular Weight:320.879
Modify Date.: 2022-11-10 22:01
Introduction: Odorless white to faint yellow crystalline powder. Bitter taste. A 10% solution in water has a pH of 3.5-5.0. View more+
1. Names and Identifiers
1.1 Name
Promethazine hydrochloride
1.2 Synonyms

)-Promethazine Hydrochloride 10-(2-(dimethylamino)propyl)phenothiazinemonohydrochloride 10-(2-(dimethylamino)propyl)-phenothiazinmonohydrochloride 10-(2-dimethylamino-1-propyl)phenothiazine hydrochloride 10-(2-Dimethylamino-2-methylethyl)phenothiazine Hydrochloride 10H-phenothiazine-10-ethanamine, N,N,a-trimethyl-, hydrochloride (1:1) 10H-Phenothiazine-10-ethanamine, N,N,α-trimethyl-, hydrochloride (1:1) EINECS 200-375-2 Genphen MFCD00012652 N-(2'-Dimethylamino-2'-methyl)ethylphenothiazine Monohydrochloride N,N,a-Trimethyl-10H-phenothiazine-10-ethanamine Monohydrochloride N,N-diméthyl-1-(10H-phénothiazin-10-yl)propan-2-amine chlorhydrate N,N-Dimethyl-1-(10H-phenothiazin-10-yl)-2-propanamine hydrochloride (1:1) N,N-Dimethyl-1-(10H-phenothiazin-10-yl)propan-2-amine hydrochloride (1:1) N,N-Dimethyl-1-(10H-phenothiazin-10-yl)propan-2-aminhydrochlorid PHENERGAN Phenothiazine, 10-[2- (dimethylamino)propyl]-, monohydrochloride Phenothiazine, 10-[2-(dimethylamino)-propyl]-, hydrochloride PROMETHAZINE HCL promethazinen-(2’-dimethylamino-2’-methylethyl)phenothiazinehydrochloride promethiazin Protazine Thiergan UNII:R61ZEH7I1I

1.3 CAS No.
58-33-3
1.4 CID
6014
1.5 EINECS(EC#)
200-375-2
1.6 Molecular Formula
C17H21ClN2S (isomer)
1.7 Inchi
InChI=1S/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
1.8 InChkey
XXPDBLUZJRXNNZ-UHFFFAOYSA-N
1.9 Canonical Smiles
CC(CN1C2=CC=CC=C2SC3=CC=CC=C31)N(C)C.Cl
1.10 Isomers Smiles
CC(CN1C2=CC=CC=C2SC3=CC=CC=C31)N(C)C.Cl
2. Properties
2.1 Density
1.131
2.1 Melting point
230-232℃
2.1 Boiling point
403.7 °C at 760 mmHg
2.1 Flash Point
198 °C
2.1 Precise Quality
320.11100
2.1 PSA
31.78000
2.1 logP
5.10640
2.1 Λmax
297nm(H2O)(lit.)
2.2 Appearance
white or off white powder
2.3 Storage
Refrigerator
2.4 Chemical Properties
White Solid
2.5 Color/Form
Crystals
WHITE TO FAINT YELLOW CRYSTALLINE POWDER
2.6 PH
pH (50g/L, 25℃) : 4.0~6.0
2.7 Water Solubility
Practically insol in acetone, ether, ethyl acetate
Very sol in dil hydrogen chloride
In water, 15.6 mg/l @ 24 deg C
2.8 Spectral Properties
IR: 5185 (Coblentz Society Spectral Collection)
MASS: 2-262 (Archives of Mass Spectral Data, John Wiley & Sons, New York)
MASS: 2088 (National Bureau of Standards EPA-NIH Mass Spectra Data Base, NSRDS-NBS-63)
Intense mass spectral peaks: 72 m/z, 199 m/z, 213 m/z, 284 m/z
2.9 StorageTemp
2-8°C
3. Use and Manufacturing
3.1 Definition
ChEBI: The hydrochloride salt of promethazine.
3.2 General Description
Odorless white to faint yellow crystalline powder. Bitter taste. A 10% solution in water has a pH of 3.5-5.0.
3.3 Usage
Antihistaminic, antiemetic, CNS depressant
4. Safety and Handling
4.1 Symbol
GHS07;GHS09;
4.1 Hazard Codes
Xn
4.1 Signal Word
Warning
4.1 Risk Statements
R22;R36/37/38
4.1 Safety Statements
S26;S36
4.1 Exposure Standards and Regulations
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
4.2 Packing Group
III
4.2 Octanol/Water Partition Coefficient
log Kow = 4.81
4.3 Fire Hazard
Flash point data for Promethazine hydrochloride are not available; however, Promethazine hydrochloride is probably combustible.
4.4 Hazard Class
6.1(b)
4.4 Hazard Declaration
H302 + H332; H315; H317; H319; H335; H411
4.4 DisposalMethods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
4.5 RIDADR
UN 2811
4.5 Safety Profile
Poison by ingestion,subcutaneous, intraperitoneal, andintravenous routes. Human systemic effectsby ingestion: excitement, sleep, convulsions,rigdity. Experimental teratogenic effects.Other experimental reproductive effects.When heated to decomposition it emits verytoxic fumes of HCl, SOx, and NOx. Used asan antihstamine.
4.6 Caution Statement
P261-P273-P280-P304 + P340 + P312-P333 + P313-P337 + P313
4.6 Formulations/Preparations
Atosil; Fargan; Fenazil; Diprazin; Provigan; Prorex; Diphergan; Ganphen; Fellozine; Remsed; Dorme; Fenergan; Lergigan; Phenergan; Promantine; Protazine; Prothazin; Thiergan. /Promethazine hydrochloride/
4.7 WGK Germany
3
4.7 RTECS
SO8225000
4.7 Protective Equipment and Clothing
A severe eye irritant.
4.8 Report

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.

4.9 Skin, Eye, and Respiratory Irritations
A severe eye irritant.
4.10 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.

4.11 Toxicity

CHEMICAL IDENTIFICATION

RTECS NUMBER :
SO8225000
CHEMICAL NAME :
Phenothiazine, 10-(2-(dimethylamino)propyl)-, monohydrochloride
CAS REGISTRY NUMBER :
58-33-3
LAST UPDATED :
199706
DATA ITEMS CITED :
22
MOLECULAR FORMULA :
C17-H20-N2-S.Cl-H
MOLECULAR WEIGHT :
320.91
WISWESSER LINE NOTATION :
T C666 BN ISJ B1Y1&N1&1 &GH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human
DOSE/DURATION :
3500 ug/kg/D
TOXIC EFFECTS :
Behavioral - sleep Behavioral - convulsions or effect on seizure threshold Behavioral - rigidity (including catalepsy)
REFERENCE :
AJPSAO American Journal of Psychiatry. (American Psychiatric Assoc., Circulation Dept., 1400 K St., NW, Washington, DC 20005) V.78- 1921- Volume(issue)/page/year: 113,654,1957
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - child
DOSE/DURATION :
20 mg/kg
TOXIC EFFECTS :
Behavioral - excitement Behavioral - changes in motor activity (specific assay) Behavioral - stiffness
REFERENCE :
LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 1,368,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
170 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
CKFRAY Ceskoslovenska Farmacie. (PNS-Ustredni Expedice a Dovoz Tisku, Kafkova 19, 160 00 Prague 6, Czechoslovakia) V.1- 1952- Volume(issue)/page/year: 15,526,1966
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
400 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YAKUD5 Gekkan Yakuji. Pharmaceuticals Monthly. (Yakugyo Jihosha, Inaoka Bldg., 2-36 Jinbo-cho, Kanda, Chiyoda-ku, Tokyo 101, Japan) V.1- 1959- Volume(issue)/page/year: 22,375,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
15 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YAKUD5 Gekkan Yakuji. Pharmaceuticals Monthly. (Yakugyo Jihosha, Inaoka Bldg., 2-36 Jinbo-cho, Kanda, Chiyoda-ku, Tokyo 101, Japan) V.1- 1959- Volume(issue)/page/year: 22,375,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
255 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes
REFERENCE :
AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 135,364,1962
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
160 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
CKFRAY Ceskoslovenska Farmacie. (PNS-Ustredni Expedice a Dovoz Tisku, Kafkova 19, 160 00 Prague 6, Czechoslovakia) V.1- 1952- Volume(issue)/page/year: 15,526,1966
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
240 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YAKUD5 Gekkan Yakuji. Pharmaceuticals Monthly. (Yakugyo Jihosha, Inaoka Bldg., 2-36 Jinbo-cho, Kanda, Chiyoda-ku, Tokyo 101, Japan) V.1- 1959- Volume(issue)/page/year: 22,375,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
50 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 108,340,1953
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
250 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NYKZAU Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. (Nippon Yakuri Gakkai, c/o Kyoto Daigaku Igakubu Yakurigaku Kyoshitsu, Konoe-cho, Yoshida, Sakyo-ku, Kyoto 606, Japan) V.40- 1944- Volume(issue)/page/year: 54,688,1958
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
35 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
PHARAT Pharmazie. (VEB Verlag Volk und Gesundheit, Neue Gruenstr. 18, Berlin DDR-1020, Ger. Dem. Rep.) V.1- 1946- Volume(issue)/page/year: 38,749,1983
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
42500 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 113,313,1958 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
666 mg/kg/16D-I
TOXIC EFFECTS :
Related to Chronic Data - death
REFERENCE :
NTPTR* National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No.206- Volume(issue)/page/year: NTP-TR-425,1993
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
2164 mg/kg/13W-I
TOXIC EFFECTS :
Sense Organs and Special Senses (Olfaction) - effect, not otherwise specified Liver - changes in liver weight
REFERENCE :
NTPTR* National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No.206- Volume(issue)/page/year: NTP-TR-425,1993
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
900 mg/kg/16D-I
TOXIC EFFECTS :
Liver - changes in liver weight Related to Chronic Data - death
REFERENCE :
NTPTR* National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No.206- Volume(issue)/page/year: NTP-TR-425,1993
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2925 mg/kg/13W-I
TOXIC EFFECTS :
Liver - changes in liver weight Related to Chronic Data - death
REFERENCE :
NTPTR* National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No.206- Volume(issue)/page/year: NTP-TR-425,1993 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
60 mg/kg
SEX/DURATION :
female 5-16 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
REFERENCE :
RCOCB8 Research Communications in Chemical Pathology and Pharmacology. (PJD Pub. Ltd., P.O. Box 966, Westbury, NY 11590) V.1- 1970- Volume(issue)/page/year: 7,701,1974
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
240 mg/kg
SEX/DURATION :
female 5-16 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility
REFERENCE :
RCOCB8 Research Communications in Chemical Pathology and Pharmacology. (PJD Pub. Ltd., P.O. Box 966, Westbury, NY 11590) V.1- 1970- Volume(issue)/page/year: 7,701,1974 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 81480 No. of Facilities: 946 (estimated) No. of Industries: 2 No. of Occupations: 5 No. of Employees: 7809 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 81480 No. of Facilities: 292 (estimated) No. of Industries: 1 No. of Occupations: 4 No. of Employees: 8796 (estimated) No. of Female Employees: 7472 (estimated)
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Skin irritation, Category 2

Skin sensitization, Category 1

Eye irritation, Category 2

Acute toxicity - Inhalation, Category 4

Specific target organ toxicity \u2013 single exposure, Category 3

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H302 Harmful if swallowed

H315 Causes skin irritation

H317 May cause an allergic skin reaction

H319 Causes serious eye irritation

H332 Harmful if inhaled

H335 May cause respiratory irritation

H411 Toxic to aquatic life with long lasting effects

Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P261 Avoid breathing dust/fume/gas/mist/vapours/spray.

P272 Contaminated work clothing should not be allowed out of the workplace.

P271 Use only outdoors or in a well-ventilated area.

P273 Avoid release to the environment.

Response

P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell.

P330 Rinse mouth.

P302+P352 IF ON SKIN: Wash with plenty of water/...

P321 Specific treatment (see ... on this label).

P332+P313 If skin irritation occurs: Get medical advice/attention.

P362+P364 Take off contaminated clothing and wash it before reuse.

P333+P313 If skin irritation or rash occurs: Get medical advice/attention.

P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

P337+P313 If eye irritation persists: Get medical advice/attention.

P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing.

P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.

P391 Collect spillage.

Storage

P403+P233 Store in a well-ventilated place. Keep container tightly closed.

P405 Store locked up.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

7. Other Information
7.0 Merck
14,7786
7.1 BRN
4166397
7.2 Overview
Promethazine (PM) ((RS)-N, N-dimethyl-1-(10H-phenothiazine-10-yl)propan-2-amine hydrochloride) is a phenothiazine derivative. It is a first-generation H1 receptor antagonist, antihistamine, and antiemetic medication and can also have strong sedative effects[1]. Promethazine affects ligand gated ion channels such as purinergic P2 or cholinergic ACh receptors and voltage dependent ion channels such as sodium, calcium, or potassium channels.
Beside, these effects, promethazine also inhibit the brain NatKt-ATPase and the mitochondrial permeability transition pore. Since its first introduction in 1946, it has been used for prevention and treatment of nausea and vomiting caused by narcotic therapy, migraine episodes, cancer chemotherapy, and so forth.[2] Meanwhile, it has become apparent that this drug interacts with many different receptors. It works by changing the actions of chemicals in brain and as an antihistamine[2]. It is used to treat allergic symptoms such as itching, runny nose, sneezing, itchy or watery eyes, hives, and itchy skin rashes, also to prevent motion sickness, and treat to nausea and vomiting pain after surgery and as a sedative or sleep aid, especially for oncologic patients. However, second-generation oral antihistamines are the preferred first-line treatment option for allergic rhinitis and urticarial, although topical first-generation antihistamines are still prescribed by general healthcare practitioner and pharmacists too easily, without taking into account possible side effects as a first line treatment for several dermatological problems[3–8].

Figure 1. The chemical structure of promethazine;
7.3 Pharmacodynamics
PM is well absorbed from the gastrointestinal tract. Peak plasma concentrations occur after 2 to 3 hours when promethazine is administered orally (25 to 50mg) or intramuscularly (25mg). Following rectal administration of promethazine in a suppository formulation, peak plasma concentrations were observed after about 8 hours. Oral bioavailability is approximately 25%. Rectal bioavailability has been reported at 23%. Promethazine is widely distributed in body tissues and has a large apparent volume of distribution following oral and intramuscular administration. Promethazine has been reported to be 93% protein-bound when determined by gas chromatography and as 76 to 80% protein-bound when determined by HPLC. Promethazine rapidly crosses the placenta, appearing in the cord blood within 1.5 minutes when given intravenously at term. Promethazine crosses the blood brain barrier. The elimination half-life of promethazine following oral administration has been estimated to be within the range of 12 to 15 hours. After intravenous administration of 12.5mg, blood concentrations of promethazine declined bio-exponentially with a terminal elimination half-life of 12 hours[5]. PM is metabolized principally to promethazine sulphoxide and to a lesser degree desmethylpromethazine. The major site of metabolism is the liver and that the drug is subjected to extensive first-pass hepatic biotransformation, explaining the oral bioavailability of 25%. Metabolism also occurs in the gut wall but to a lesser degree than earlier postulated. The sulphoxide metabolite has not been detected after intramuscular dosing as circulating levels are probably below analytical detection limits due to a combination of slow absorption, lower dose (50% of oral), and bypass of first-pass metabolism in the liver[3]. Its elimination is primarily due to hepatic metabolism. No evidence was found to suggest that metabolites of promethazine are pharmacologically or toxicologically active. Promethazine has not been reliably detected in breast milk[4].
7.4 Indications
PM is used for the treatment of allergic symptoms, often given at night because of its marked sedative effects. Drug hypersensitivity reactions and allergic conditions have also been treated with promethazine especially in emergencies. It can also be used in treating symptoms of asthma, pneumonia, or other lower respiratory tract infections; in fact, inhalation therapy for relieving bronchial spasm is made by quaternary salts of promethazine. PM is sometimes used for its sedative effects and in some countries is marketed for this purpose, including the sedation of young children as nasal sleep introducing drug, or it can be used as an anaesthetic premedication to produce sedation, reduce anxiety, or to reduce postoperative nausea and vomiting as dose-controlled transdermal device. The drug is often given in conjunction with an opiate analgesic such as pethidine, particularly in obstetrics. Taken before travelling, promethazine is effective in preventing motion sickness. Vomiting from other causes can be treated with higher or more frequent doses.
Combination of histamine H1R and H4R antagonist is used for the treatment of neoplastic disorders, consisting in a cytotoxic agent as an agent to prevent multidrug resistance[9]. It is also used as a contraceptive killing spermin vagina, since promethazine hydrochloride has strong sperm-killing effect, or as an antimutagenic treatment of bacteria by killing bacteria. Bathing preparation, which contains a histamine H1-antagonist, inhibits the decomposition of hyaluronic acid, playing an important role inmoisture and tension of skin to improve roughened or dried skin. This cosmetic can take such a form as gel, cream, spray, cataplasm, lotion, pack, milky lotion, or powder. It can also be a melanogenesis-suppressing agent useful as a skin-beautifying cosmetic, a skin-aging prevention agent, and so forth, by using a phenothiazine compound having remarkable melanogenesis-suppressing effect. Application of PM can be used for treating haemorrhoids with no pain, no side effect, no operation, and no hospitalization, but low cost[10–12]. Promethazine has been used to control extrapyramidal disorders in children caused by metoclopramide and levodopa-induced dyskinesia in patients with Parkinson’s disease. In young children undergoing dental procedures, it has been suggested that promethazine can be used in conjunction with chloral hydrate to produce sedation, as there was observed a lower incidence of nausea than when chloral hydrate was administered alone. In some countries, promethazine is available as a 2% cream without medical prescription for the treatment of allergic skin conditions, insect bites, and burns.
7.5 Mode of action
Promethazine is a phenothiazine antihistamine, antagonizing the central and peripheral effects of histamine mediated by histamine H1 receptors. The drug does not antagonize histamine at H2 receptors. Antihistamines competitively antagonize most of the smooth muscle stimulating actions of histamine on the H1 receptors of the gastrointestinal tract, uterus, large blood vessels, and bronchial muscle. Increased capillary permeability and oedema formation, flare, and pruritus, resulting from actions of histamine onH1 receptors, are also effectively antagonized. Promethazine appears to act by blocking H1 receptor sites, preventing the action of histamine on the cell. Promethazine rapidly crosses the blood brain barrier and it is thought that the sedative effects are due to blockade of H1 receptors in the brain. Promethazine is not used clinically for its antipsychotic properties but in common with other phenothiazines exhibits antidopaminergic properties. The antiemetic effect of promethazine may be due to blockade of dopaminergic receptors in the chemoreceptor trigger zone(CTZ) of the medulla. Promethazine has strong anticholinergic properties, blocking the responses to acetylcholine that are mediated by muscarinic receptors. These atropine-like actions are responsible for most of the side effects observed in clinical use of the drug. Promethazine also has antimotion sickness properties that may be due to central antimuscarinic action. In concentrations several times higher than those required to antagonize histamine, promethazine exhibits local anaesthetic effects. Promethazine has also been shown to inhibit calmodulin. Authors have suggested that calmodulin inhibition by promethazine could be a mechanism involved in the blockade of histamine secretion at cellular level[14].
7.6 Adverse reactions
Most reference texts suggest that the toxicity of promethazine is mainly due to its anticholinergic actions at muscarinic receptors. Many of the signs and symptoms of poisoning are similar to those observed with atropine. In the presence of anticholinergic effects, serious manifestations such as seizures, hallucinations, hypertension, and arrhythmias have been reversed by the administration of physostigmine. Besides anticholinergic 5 effects, promethazine can also exhibit toxic effects typical of antipsychotic phenothiazines. Hypotension and extrapyramidal signs may be attributable to antidopaminergic actions of promethazine[13].
Side effects usually reported are severe breathing problems or death in child younger than 2 years old. In adults, overdosage is usually characterized by CNS depression resulting in sedation and coma sometimes followed by excitement. In young children, CNS stimulation is dominant; symptoms include excitation, hallucinations, dystonias, and occasionally seizures. Anticholinergic manifestations such as dry mouth, mydriasis, and blurred vision are usually present. Overdosage may also present with various cardiorespiratory symptoms such as respiratory depression, tachycardia, hypertension or hypotension, and extrasystoles. Sedation, ranging from mild drowsiness to deep sleep, is probably the most common adverse effect. Dizziness, lassitude, disturbed coordination, and muscular weakness have all been reported. Gastrointestinal effects including epigastric distress, nausea, diarrhea, or constipation can occur. Promethazine can also cause immunoallergic reactions. Leucopenia and agranulocytosis have occurred rarely and usually in patients receiving promethazine in combination with other drugs known to cause these effects. Jaundice and thrombocytopenic purpura have been reported rarely. Extrapyramidal effects can occur, especially at high doses. Venous thrombosis has been reported at the site of intravenous injections. Arteriospasm and gangrene may follow inadvertent intra-arterial injection. Respiratory depression, sleep apnoea, and sudden infant death syndrome (SIDS) have occurred in a number of infants or young children who were receiving usual doses of promethazine[15–19].
7.7 References
  1. K. Yanai, “Anticholinergic activity of antihistamines,” Clinical Neurophysiology, vol. 123, no. 4, pp. 633–634, 2012.
  2. P. Tarkkila, K. Torn, M. Tuominen, and L. Lindgren, “Premedication with promethazine and transdermal scopolamine reduces the incidence of nausea and vomiting after intrathecal morphine,” Acta Anaesthesiologica Scandinavica, vol. 39, no. 7, pp. 983–986, 1995.
  3. E. R. Scherl and J. F. Wilson, “Comparison of dihydroergotamine with metoclopramide versus meperidine with promethazine in the treatment of acute migraine,” Headache, vol. 35, no. 5, pp. 256–259, 1995.
  4. A. U. Buzdar, L. Esparza, R. Natale et al., “Lorazepamenhancement of the antiemetic efficacy of dexamethasone and promethazine: a placebo-controlled study,” American Journal of Clinical Oncology, vol. 17, no. 5, pp. 417–421, 1994.
  5. J. R. Lackner and A. Graybiel, “Use of promethazine to hasten adaptation to provocative motion,” Journal of Clinical Pharmacology, vol. 34, no. 6, pp. 644–648, 1994.
  6. T. E. Terndrup, D. J. Dire, C. M. Madden, H. Davis, R. M. Cantor, and D. P. Gavula, “A prospective analysis of intramuscular meperidine, promethazine, and chlorpromazine in pediatric emergency department patients,” Annals of Emergency Medicine, vol. 20, no. 1, pp. 31–35, 1991.
  7. T. K. Lin, M.Q.Man, J. L. Santiago et al., “Topical antihistamines display potent anti-inflammatory activity linked in part to enhanced permeability barrier function,” Journal of Investigative Dermatology, vol. 133, no. 2, pp. 469–478, 2013.
  8. S. Ljubojevi′c and J. Lipozenci′c, “Reactions to insect stings and bites,” Acta Medica Croatica, vol. 65, no. 2, pp. 137–139, 2011.
  9. B. Blaya, F. Nicolau-Galm′es, S. M. Jangi et al., “Histamine and histamine receptor antagonists in cancer biology,” Inflammation and Allergy—Drug Targets, vol. 9, no. 3, pp. 146–157, 2010.
  10. C. Vidal Pan, A. Gonz′alez Quintela, P. Galdos Anuncibay, and J. Mateo Vic, “Topical promethazine intoxication,” Current Medical Research andOpinion, vol. 28, no. 4, pp. 623–642, 2012.
  11. K. Yanai, “Anticholinergic activity of antihistamines,” Clinical Neurophysiology, vol. 123, no. 4, pp. 633–634, 2012.
  12. X.-C. Wang, J.-G. Hong, and X.-Q. Yang, “Discussions on the use of promethazine,” Chinese Journal of Pediatrics, vol. 48,no. 7, pp. 557–558, 2010.
  13. “Promethazine should not be used for infants,” Pharmazie, vol. 65, no. 5, pp. 339–342, 2010.
  14. K.A. J.AlKhaja,T.M.AlAnsari, A. H. H. Damanhori, andR.P. Sequeira, “Evaluation of drug utilization and prescribing errors in infants: a primary care prescription-based study,” Health Policy, vol. 81, no. 2-3, pp. 350–357, 2007.
  15. M. R. Cohen, “Frequency and severity of promethazine adverse event reports obligated the ISMP alert,” Joint Commission Journal on Quality and Patient Safety, vol. 36, no. 3, pp. 143–144, 2010.
  16. J. Lazarou, B. H. Pomeranz, and P. N. Corey, “Incidence of adverse drug reactions in hospitalized patients: a metaanalysis of prospective studies,” Journal of the American Medical Association, vol. 279, no. 15, pp. 1200–1205, 1998.
  17. T.K.Gandhi, S.N.Weingart, J.Borus et al., “Adversedrug events in ambulatory care,”The New England Journal of Medicine, vol. 348, no. 16, pp. 1556–1564, 2003.
  18. D. Vervloet and S. Durham, “ABC of allergies: adverse reactions to drugs,” British Medical Journal, vol. 316, no. 7143, pp. 1511–1514, 1998.
  19. L. M. Sylvia, “Drug allergy, pseudoallergy, and cutaneous diseases,” in Drug-Induced Diseases: Prevention, Detection, and Management, J. E. Tisdale and D. A. Miller, Eds., American Society ofHealth-System Pharmacists, Bethesda,Md, USA, 2nd edition, 2010.
7.8 Chemical Properties
White Solid
7.9 Uses
Antihistaminic, antiemetic, CNS depressant
7.10 Uses
stool softener
7.11 Uses
For the treatment of allergic disorders, and nausea/vomiting.
7.12 Uses
Promethazine is a first generation histamine H1 receptor antagonist (Ki = 2.6 nM) whose antihistamine activity has been reported in guinea pigs and mice at ED50 values of 0.43 and 5.9 mg/kg, respectively. Promethazine can penetrate the CNS, depressing central H1 receptor activity, which may relate to its sedative properties, and can also inhibit muscarinic acetylcholine receptors (Ki = 22 nM). Furthermore, 32 mg/kg promethazine demonstrates antiemetic effects in ferret models of motion sickness or chemotherapy-induced nausea.
7.13 Uses
Promethazine hydrochloride is used as antihistamine; antiemetic; central nervous system depressant; sedative; anticholinergic; antiserotoninergic; local anesthetic; in the treatment of motion sickness, cough linctuses, nausea, and allergic conditions; used to control Parkinsonian symptoms and as central nervous system depressant; in pills, syrup, injections and suppositories.
7.14 Definition
ChEBI: The hydrochloride salt of promethazine.
7.15 Brand name
Phenergan (Wyeth).
7.16 General Description
Odorless white to faint yellow crystalline powder. Bitter taste. A 10% solution in water has a pH of 3.5-5.0.
7.17 General Description
Promethazine hydrochloride,(±)10-[2-(dimethylamino)-propyl]phenothiazinemonohydrochloride (Phenergan), occurs as a white tofaint yellow crystalline powder that is very soluble in water,in hot absolute alcohol, and in chloroform. Its aqueous solutionsare slightly acid to litmus.
7.18 Air & Water Reactions
Slowly oxidizes in air, acquiring a blue color. Also turns blue on exposure to moisture. Water soluble.
7.19 Reactivity Profile
Promethazine hydrochloride is sensitive to light. In aqueous solution, Promethazine hydrochloride is degraded by heat and light (more rapidly in air or oxygen). Incompatible with alkalis and alkaline solutions such as those of aminophylline, soluble barbiturates and phenytoin sodium. Iron(III) and copper(III) accelerate the degradation .
7.20 Fire Hazard
Flash point data for Promethazine hydrochloride are not available; however, Promethazine hydrochloride is probably combustible.
7.21 Safety Profile
Poison by ingestion, subcutaneous, intraperitoneal, and intravenous routes. Human systemic effects by ingestion: excitement, sleep, convulsions, rigdity. Experimental teratogenic effects. Other experimental reproductive effects. When heated to decomposition it emits very toxic fumes of HCl, SOx, and NOx. Used as an antihstamine.
7.22 Veterinary Drugs and Treatments
Promethazine may be useful in dogs and cats as an antiemetic. Because of its antihistamine actions, it has been tried for treating pruritus in atopic dogs, but its efficacy has been poor.
7.23 Dosage forms
12.5 mg PO q.i.d.; 25 mg PO at bedtime. May contain saccharin.
8. Computational chemical data
  • Molecular Weight: 320.879g/mol
  • Molecular Formula: C17H21ClN2S
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 320.1113975
  • Monoisotopic Mass: 320.1113975
  • Complexity: 298
  • Rotatable Bond Count: 3
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Topological Polar Surface Area: 31.8
  • Heavy Atom Count: 21
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count: 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 2
  • CACTVS Substructure Key Fingerprint: AAADceB7AABEAAAAAAAAAAAAAAAAAAAAAAA8YIAAAAAAAACxQAAAHAQAAAAACCjBUAQywYMAAAiAACRCQACCAAAhChAIiBwIZIgIYGLgkZGUIAhggADoyAcQAAAAAAAAAAAAAQAAAAAAAAACAAAAAAAAAA==
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10. Realated Product Infomation