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69-09-0

69-09-0 structure
69-09-0 structure
  • Name: Chlorpromazine hydrochloride
  • Chemical Name: chlorpromazine hydrochloride
  • CAS Number: 69-09-0
  • Molecular Formula: C17H20Cl2N2S
  • Molecular Weight: 355.325
  • Catalog: API Nervous system medication Antipsychotic
  • Create Date: 2018-10-03 11:00:34
  • Modify Date: 2024-01-02 13:24:24
  • Chlorpromazine Hydrochloride is an antagonist of the dopamine D2, 5HT2A, potassium channel andsodium channel. Chlorpromazine binds with D2 and 5HT2A with Kis of 363 nM and 8.3 nM, respectively.
Name chlorpromazine hydrochloride
Synonyms CHLORAZIN
CHLORPROMAZINE HCL
chloracetil
Hibernal
Phenothiazine, 2-chloro-10-(3-dimethylaminopropyl)-, hydrochloride
2-Chloro-10-[3-(dimethylamino)-1-propyl]phenothiazine Hydrochloride
Chloropromazin hydrochloride
Phenothiazine, 2-chloro-10-[3- (dimethylamino)propyl]-, monohydrochloride
Fenactil monohydrochloride
Ampliactil
hibanil
UNII-9WP59609J6
Plegomazin
Largactil
10H-Phenothiazine-10-propanamine, 2-chloro-N,N-dimethyl-, hydrochloride (1:1)
Contomin hydrochloride
3-(2-Chloro-10H-phenothiazin-10-yl)-N,N-dimethylpropan-1-amine hydrochloride (1:1)
Aminazin Hydrochloride
Propaphenin
Largaktyl
Chlorpromazine hydrochloride
Thorazine
Chloractil
Megaphen
MFCD00012654
Chlorpromazine monohydrochloride
EINECS 200-701-3
2-Chloro-10-(3-dimethylaminopropyl)phenothiazine monohydrochloride
Propaphen
CHLOROPROMAZINE HYDROCHLORIDE
Taroctyl
3-(2-Chloro-10H-phenothiazin-10-yl)-N,N-dimethyl-1-propanamine hydrochloride (1:1)
Chlorpromazine (hydrochloride)
Description Chlorpromazine Hydrochloride is an antagonist of the dopamine D2, 5HT2A, potassium channel andsodium channel. Chlorpromazine binds with D2 and 5HT2A with Kis of 363 nM and 8.3 nM, respectively.
Related Catalog
Target

Ki: 363 nM (dopamine D2 receptor), 8.3 nM (5-HT2A receptor)[4]

In Vitro Chlorpromazine (3, 10, 20, 40, and 60 μM) decreases the peak currents of hNav1.7 in a concentration-dependent manner, with IC50 of 25.9 μM with a Hill coefficient of 2.3. Chlorpromazine (25 μM) produces strong use-dependent inhibition of the hNav1.7 current. Chlorpromazine blocks the hNav1.7 channel, independent of calmodulin[1]. Chlorpromazine blocks HERG potassium channels with an IC50 value of 21.6 μM and a Hill coefficient of 1.11. Chlorpromazine (1, 10, 100 μM) blocks HERG potassium channels expressed in Xenopus laevis oocytes in a concentration-dependent manner. Chlorpromazine blocks HERG potassium channels in the activated state[5].
In Vivo Chlorpromazine (2 mg/kg, i.p.)-induced neurobehavioural abnormalities (NAs) are characterized by significant increase in cataleptic behaviour and loared spontaneous activity reaction time in mice[2]. Chlorpromazine (1 or 5 mg/kg, i,p.) prevents ketamine (KET) from increasing average spectral power of delta and gamma-high bands on the 5th and 10th days of treatment in rats[3].
Animal Admin Adult mice (8-10 weeks old) weighing 18-25 g are divided into five groups of six mice per group. The treatment schedule is as follows: Group 1, control (Normal Saline: NS, 10 mL/kg i.p.); Group 2, chlorpromazine (CPZ, 2 mg/kg i.p.); Group 3, bromocriptine (BMC, 2.5 mg/kg s.c.); Group 4: amlodipine (AML, 1 mg/kg s.c.); Group 5, BMC (2.5 mg/kg s.c.) + AML (1 mg/kg). Animal treated with BMC or AML or their combination also receive chlorpromazine 30 min later (i.p.). Animals are subjected to various tests including metal bar test for catalepsy and spontaneous activity wheel for motor assessment and agility and elevated plus maze, hole-board, Y-maze, open-field tests for locomotory activity, and exploratory behaviour respectively. Animals are euthanized eighteen hours later by cervical dislocation. The brain is dissected, rinsed in buffer (pH 7.6) and homogenized with Teflon and used for assessment of lipid peroxidation, reduced glutathione, superoxide dismutase and catalase.
References

[1]. Lee SJ, et al. Mechanism of inhibition by chlorpromazine of the human pain threshold sodium channel, Nav1.7. Neurosci Lett. 2017 Feb 3;639:1-7

[2]. Kale OE, et al. Amlodipine, an L-type calcium channel blocker, protects against chlorpromazine-induced neurobehavioural deficits in mice. Fundam Clin Pharmacol. 2017 Jan 19

[3]. Sampaio LR, et al. Electroencephalographic study of chlorpromazine alone or combined with alpha-lipoic acid in a model of schizophrenia induced by ketamine in rats. J Psychiatr Res. 2017 Mar;86:73-82

[4]. Suzuki H, et al. Comparison of the anti-dopamine D? and anti-serotonin 5-HT(2A) activities of chlorpromazine, bromperidol, haloperidol and second-generation antipsychotics parent compounds and metabolites thereof. J Psychopharmacol. 2013 Apr;27(4):396-400

[5]. Thomas, D., et al. The antipsychotic drug chlorpromazine inhibits HERG potassium channels. Br J Pharmacol, 2003. 139(3): p. 567-74.
Density 1.077 g/cm3 (15 C)
Boiling Point 450.1ºC at 760 mmHg
Melting Point 192-196°C
Molecular Formula C17H20Cl2N2S
Molecular Weight 355.325
Exact Mass 354.072418
PSA 31.78000
LogP 5.76140
Index of Refraction 1.4436 (20ºC)
Stability Stable. Combustible. Incompatible with strong oxidizing agents. Air and light sesnsitive.
Water Solubility >=10 g/100 mL at 24 ºC

CHEMICAL IDENTIFICATION

RTECS NUMBER :
SO1750000
CHEMICAL NAME :
Phenothiazine, 2-chloro-10-(3-(dimethylamino)propyl)-, monohydrochloride
CAS REGISTRY NUMBER :
69-09-0
LAST UPDATED :
199710
DATA ITEMS CITED :
54
MOLECULAR FORMULA :
C17-H19-Cl-N2-S.Cl-H
MOLECULAR WEIGHT :
355.35
WISWESSER LINE NOTATION :
T C666 BN ISJ B3N1&1 EG &GH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
6071 ug/kg
TOXIC EFFECTS :
Reproductive - Paternal Effects - other effects on male
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
18 mg/kg
TOXIC EFFECTS :
Reproductive - Paternal Effects - other effects on male
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
6 mg/kg
TOXIC EFFECTS :
Behavioral - anorexia (human) Gastrointestinal - other changes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
35 gm/kg/16Y-I
TOXIC EFFECTS :
Behavioral - rigidity (including catalepsy) Cardiac - pulse rate increase, without fall in BP Lungs, Thorax, or Respiration - respiratory stimulation
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
1786 ug/kg/2D-I
TOXIC EFFECTS :
Behavioral - irritability Lungs, Thorax, or Respiration - respiratory stimulation Skin and Appendages - sweating
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
822 ug/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - excitement Cardiac - pulse rate increase, without fall in BP
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
145 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LC50 - Lethal concentration, 50 percent kill
ROUTE OF EXPOSURE :
Inhalation
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
40 mg/m3/2H
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
62 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
25 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
90 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
135 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - rigidity (including catalepsy) Behavioral - alteration of classical conditioning
TYPE OF TEST :
LC50 - Lethal concentration, 50 percent kill
ROUTE OF EXPOSURE :
Inhalation
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
40 mg/m3/2H
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
92200 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
420 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
20 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Primate - monkey
DOSE/DURATION :
>30 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - muscle weakness Behavioral - rigidity (including catalepsy)
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
5 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
109 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
420 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Bird - chicken
DOSE/DURATION :
160 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Bird - chicken
DOSE/DURATION :
28 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
900 mg/kg/30D-I
TOXIC EFFECTS :
Related to Chronic Data - changes in ovarian weight Related to Chronic Data - changes in uterine weight
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
50 mg/kg/5D-I
TOXIC EFFECTS :
Related to Chronic Data - changes in ovarian weight Related to Chronic Data - changes in uterine weight
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
300 mg/kg
SEX/DURATION :
female 6-20 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - behavioral
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
50 mg/kg
SEX/DURATION :
female 7-16 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
250 mg/kg
SEX/DURATION :
female 7-16 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
350 mg/kg
SEX/DURATION :
female 7-16 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1980 mg/kg
SEX/DURATION :
male 4 week(s) pre-mating female 4 week(s) pre-mating - 3 week(s) post-birth
TOXIC EFFECTS :
Reproductive - Effects on Newborn - biochemical and metabolic
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
2500 ug/kg
SEX/DURATION :
male 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - mating performance (e.g. # sperm positive females per # females mated; # copulations per # estrus cycles)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
25 mg/kg
SEX/DURATION :
female 8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - extra-embryonic structures (e.g., placenta, umbilical cord) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
100 mg/kg
SEX/DURATION :
female 14 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - stillbirth Reproductive - Effects on Newborn - live birth index (measured after birth) Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
100 mg/kg
SEX/DURATION :
female 14 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Specific Developmental Abnormalities - gastrointestinal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
50 mg/kg
SEX/DURATION :
female 12 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
12 mg/kg
SEX/DURATION :
female 12-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - biochemical and metabolic
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
24 mg/kg
SEX/DURATION :
female 17-20 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - postpartum Reproductive - Effects on Newborn - stillbirth Reproductive - Effects on Newborn - weaning or lactation index (e.g., # alive at weaning per # alive at day 4)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
12 mg/kg
SEX/DURATION :
female 12-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - behavioral
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
24 mg/kg
SEX/DURATION :
female 17-20 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - stillbirth Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
125 mg/kg
SEX/DURATION :
male 5 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - testes, epididymis, sperm duct
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
300 mg/kg
SEX/DURATION :
female 6-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Specific Developmental Abnormalities - urogenital system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
300 mg/kg
SEX/DURATION :
female 6-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - eye/ear
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
150 mg/kg
SEX/DURATION :
female 6-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
21 mg/kg
SEX/DURATION :
female 9 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
10 mg/kg
SEX/DURATION :
female 3 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - cytological changes (including somatic cell genetic material) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - other effects to embryo

MUTATION DATA

TEST SYSTEM :
Rodent - rat
DOSE/DURATION :
25 mg/kg
REFERENCE :
DCTODJ Drug and Chemical Toxicology. (Marcel Dekker, 270 Madison Ave., New York, NY 10016) V.1- 1977/78- Volume(issue)/page/year: 9,41,1986 *** REVIEWS *** TOXICOLOGY REVIEW JMSCA9 Journal of Mental Science. (London, UK) V.4-108, 1857-1962. For publisher information, see BJPYAJ. Volume(issue)/page/year: 106,755,1960 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - M1050 No. of Facilities: 830 (estimated) No. of Industries: 2 No. of Occupations: 3 No. of Employees: 905 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - M1050 No. of Facilities: 188 (estimated) No. of Industries: 1 No. of Occupations: 3 No. of Employees: 3661 (estimated) No. of Female Employees: 1936 (estimated)
Symbol GHS06
GHS06
Signal Word Danger
Hazard Statements H301-H330
Precautionary Statements P260-P284-P301 + P310-P310
Personal Protective Equipment Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges
Hazard Codes T+
Risk Phrases R25
Safety Phrases S28-S36/37-S45
RIDADR UN 2811 6.1/PG 1
WGK Germany 3
RTECS SO1750000
Packaging Group III
Hazard Class 6.1(b)
HS Code 2932999099
Flash Point(F) 48.2 °F
Flash Point(C) 9 °C
HS Code 2934300000
Summary 2934300000. other compounds containing in the structure a phenothiazine ring-system (whether or not hydrogenated), not further fused. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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