Perphenazine

Names

[ CAS No. ]:
58-39-9

[ Name ]:
Perphenazine

[Synonym ]:
1-Piperazineethanol, 4-[3-(2-chlorophenothiazin-10-yl)propyl]-
2-{4-[3-(2-Chlor-10H-phenothiazin-10-yl)propyl]piperazin-1-yl}ethanol
2-{4-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]piperazin-1-yl}ethanol
2-(4-(3-(2-Chloro-10H-phenothiazin-10-yl)propyl)piperazin-1-yl)ethanol
2-{4-[3-(2-Chloro-10H-phenothiazin-10-yl)propyl]-1-piperazinyl}ethanol
EINECS 200-381-5
1-Piperazineethanol, 4-(3-(2-chloro-10H-phenothiazin-10-yl)propyl)-
Chlorpiprozine
1-(2-Hydroxyethyl)-4-[3-(2-chloro-10-phenothiazinyl)propyl]piperazine
2-Chloro-10-[3-[1-(2-hydroxyethyl)-4-piperazinyl]propyl]phenothiazine
4-[3-(2-Chloro-10H-phenothiazin-10-yl)propyl]-1-piperazineethanol
2-{4-[3-(2-chloro-10H-phénothiazin-10-yl)propyl]pipérazin-1-yl}éthanol
1-Piperazineethanol, 4-[3- (2-chloro-10H-phenothiazin-10-yl)propyl]-
Trilafon
MFCD00056798
2-Chloro-10-[3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl]phenothiazine
PZC
g-[4-(b-Hydroxyethyl)piperazin-1-yl]propyl-2-chlorophenothiazine
1-Piperazineethanol, 4-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]-
2-{4-[3-(2-Chloro-phenothiazin-10-yl)-propyl]-piperazin-1-yl}-ethanol
Perphenazine
2-[4-[3-(2-Chlorophenothiazin-10-yl)propyl]piperazin-1-yl]ethanol

Biological Activity

[Description]:

Perphenazine is a typical antipsychotic drug, inhibits 5-HT2Areceptor, Alpha-1A adrenergic receptor, Dopamine receptor D2/D3, D2L receptor, and Histamine H1 receptor, with Ki values of 5.6, 10, 0.765/0.13, 3.4, and 8 nM, respectively.

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> 5-HT Receptor

Signaling Pathways >> Neuronal Signaling >> 5-HT Receptor

Signaling Pathways >> GPCR/G Protein >> Adrenergic Receptor

Signaling Pathways >> GPCR/G Protein >> Dopamine Receptor

Signaling Pathways >> Neuronal Signaling >> Dopamine Receptor

Signaling Pathways >> GPCR/G Protein >> Histamine Receptor

Signaling Pathways >> Immunology/Inflammation >> Histamine Receptor

Research Areas >> Neurological Disease

[Target]

5-HT2A Receptor:5.6 nM (Ki)

H1 receptor:8 nM (Ki)

α1A adrenergic receptor:10 nM (Ki)

D2 receptor:0.765 nM (Ki)

D3 receptor:0.13 nM (Ki)

D2L receptor:3.4 nM (Ki)

[References]

[1]. Richtand NM, et al. Dopamine and serotonin receptor binding and antipsychotic efficacy. Neuropsychopharmacology. 2007 Aug;32(8):1715-26.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
580.4±50.0 °C at 760 mmHg

[ Melting Point ]:
35339ºC

[ Molecular Formula ]:
C₂₁H₂₆ClN₃OS

[ Molecular Weight ]:
403.969

[ Flash Point ]:
304.8±30.1 °C

[ Exact Mass ]:
403.148499

[ PSA ]:
55.25000

[ LogP ]:
4.34

[ Vapour Pressure ]:
0.0±1.7 mmHg at 25°C

[ Index of Refraction ]:
1.627

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: TL7175000

CHEMICAL NAME :: 1-Piperazineethanol, 4-(3-(2-chlorophenothiazin-10-yl)propyl)-

CAS REGISTRY NUMBER :: 58-39-9

LAST UPDATED :: 199504

DATA ITEMS CITED :: 35

MOLECULAR FORMULA :: C21-H26-Cl-N3-O-S

MOLECULAR WEIGHT :: 404.01

WISWESSER LINE NOTATION :: T C666 BN ISJ EG B3- AT6N DNTJ D2Q

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Human

DOSE/DURATION :: 71428 ng/kg

TOXIC EFFECTS :: Behavioral - muscle contraction or spasticity

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 318 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 - rat

DOSE/DURATION :: 146 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 - rat

DOSE/DURATION :: >80 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 :: 34 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 :: 120 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 - mouse

DOSE/DURATION :: 64 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 - mouse

DOSE/DURATION :: >80 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity)

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 19 mg/kg

TOXIC EFFECTS :: Behavioral - ataxia Behavioral - rigidity (including catalepsy)

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: >20 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 :: Mammal - dog

DOSE/DURATION :: 51 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - rigidity (including catalepsy) Gastrointestinal - hypermotility, diarrhea

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: >510 ug/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 :: Mammal - cat

DOSE/DURATION :: 1 gm/kg

TOXIC EFFECTS :: Gastrointestinal - hypermotility, diarrhea

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: >2500 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 :: Intravenous

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 35 mg/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - spastic paralysis with or without sensory change Behavioral - convulsions or effect on seizure threshold Gastrointestinal - hypermotility, diarrhea

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Bird - pigeon

DOSE/DURATION :: 32 mg/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - spastic paralysis with or without sensory change Behavioral - convulsions or effect on seizure threshold Gastrointestinal - hypermotility, diarrhea

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Bird - pigeon

DOSE/DURATION :: 250 mg/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - spastic paralysis with or without sensory change Behavioral - convulsions or effect on seizure threshold Gastrointestinal - hypermotility, diarrhea

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - wild bird species

DOSE/DURATION :: 32 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

DOSE :: 90 mg/kg

SEX/DURATION :: female 14 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - blood and lymphatic systems (including spleen and marrow)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 90 mg/kg

SEX/DURATION :: female 13 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - urogenital system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 150 mg/kg

SEX/DURATION :: female 10 day(s) after conception

TOXIC EFFECTS :: 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 15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Parenteral

DOSE :: 80 mg/kg

SEX/DURATION :: female 1-8 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 70 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 :: Oral

DOSE :: 30 mg/kg

SEX/DURATION :: female 10-12 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 75 mg/kg

SEX/DURATION :: female 10-12 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 :: 150 mg/kg

SEX/DURATION :: female 10-12 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 25 mg/kg

SEX/DURATION :: female 9 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - Central Nervous System

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 4 mg/kg

SEX/DURATION :: female 1 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - other measures of fertility

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 4 mg/kg

SEX/DURATION :: female 1 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - other measures of fertility

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 10500 ug/kg

SEX/DURATION :: female 42-44 week(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects Endocrine - estrogenic

MUTATION DATA

TYPE OF TEST :: Cytogenetic analysis

TEST SYSTEM :: Human Leukocyte

DOSE/DURATION :: 270 mg/kg

REFERENCE :: BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 3,634,1969 *** 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 TOXICOLOGY REVIEW IDPYAK Industrial Pharmacology. (Mount Kisco, NY) V.1-3, 1974-79. Discontinued. Volume(issue)/page/year: 1,203,1974 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X4452 No. of Facilities: 127 (estimated) No. of Industries: 2 No. of Occupations: 11 No. of Employees: 13092 (estimated) No. of Female Employees: 9582 (estimated)

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H317

[ Precautionary Statements ]:
P280-P301 + P312 + P330

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
28-36/37/39-45

[ RIDADR ]:
UN 2811 6.1 / PGII

[ WGK Germany ]:
3

[ RTECS ]:
TL7175000

[ HS Code ]:
2934999090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2934999090

[ Summary ]:
2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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