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Basic Information
CAS No.: 15574-96-6
Name: Pizotifen
Molecular Structure:
Molecular Structure of 15574-96-6 (Pizotifen)
Formula: C19H21 N S
Molecular Weight: 295.44
Synonyms: 4H-Benzo[4,5]cyclohepta[1,2-b]thiophene,piperidine deriv.; 4-(1-Methyl-4-piperidylidene)-9,10-dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thiophene;4-(9,10-Dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thien-4-ylidene)-1-methylpiperidine;BC 105; Litec; Pizotifen; Pizotyline; Polomigran; Sandomigran
EINECS: 239-632-9
Density: 1.164g/cm3
Melting Point: 140-142°C
Boiling Point: 436.7°Cat760mmHg
Flash Point: 217.9°C
Hazard Symbols: Xi,Xn
Risk Codes: 36/37/38-22-63
Safety: 26-37/39-36/37
PSA: 31.48000
LogP: 4.31210
Related products
Synthetic route
15574-96-6

pizotifen

1176736-68-7

4-(2-bromo-9,10-dihydro-1-thiabenzo[f]-azulen-4-ylidene)-1-methylpiperidine

Conditions
ConditionsYield
With bromine In chloroform at 0 - 20℃; for 2h;91%
With bromine In chloroform at 0 - 20℃; for 2h;91%
15574-96-6

pizotifen

C19H20(2)HNS

Conditions
ConditionsYield
With water-d2; silver In dimethyl sulfoxide at 40℃; for 12h;75%
541-41-3

chloroformic acid ethyl ester

15574-96-6

pizotifen

23455-54-1

4-(9,10-dihydro-benzo[4,5]cyclohepta[1,2-b]thiophen-4-ylidene)-piperidine-1-carboxylic acid ethyl ester

Conditions
ConditionsYield
With triethylamine In toluene at 60℃; Reflux;9%
15574-96-6

pizotifen

1176739-91-5

Ethyl 4-(2-bromo-9,10-dihydro-1-thia-benzo[f]azulen-4-ylidene)piperidine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / toluene / 60 °C / Reflux
2: bromine / chloroform / 2 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: bromine / chloroform / 2 h / 0 - 20 °C
2: toluene / 6 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: bromine / chloroform / 2 h / 0 - 20 °C
2: toluene / 6 h / Reflux
View Scheme
15574-96-6

pizotifen

1176739-46-0

3-[4-piperidin-4-ylidene-4H-1-thiabenzo[f]azulen-2-yl]-propionic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: triethylamine / toluene / 60 °C / Reflux
2.1: trichlorophosphate / 1,2-dichloro-ethane / 1.5 h / 0 - 20 °C
2.2: 37 h / 50 °C
2.3: 1 h / 20 °C
3.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 20 °C / Inert atmosphere; Cooling
3.2: 2 h / 20 °C
4.1: hydrogen bromide / acetic acid / 4 h / 120 °C
4.2: 3 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: triethylamine / toluene / 60 °C / Reflux
2.1: bromine / chloroform / 2 h / 20 °C
3.1: triethylamine; tri-ortho-toluoylphosphine / palladium diacetate / N,N-dimethyl-formamide / 80 °C / Inert atmosphere
4.1: hydrogen bromide / acetic acid / 4 h / 120 °C
4.2: 3 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: bromine / chloroform / 2 h / 0 - 20 °C
2.1: toluene / 6 h / Reflux
3.1: triethylamine; tri-ortho-toluoylphosphine / palladium diacetate / N,N-dimethyl-formamide / 80 °C / Inert atmosphere
4.1: hydrogen bromide / acetic acid / 4 h / 120 °C
4.2: 3 h / 20 °C
View Scheme
15574-96-6

pizotifen

ethyl 4-(2-formyl-9,10-dihydro-1-thia-benzo[f]azulen-4-ylidene)piperidine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triethylamine / toluene / 60 °C / Reflux
2.1: trichlorophosphate / 1,2-dichloro-ethane / 1.5 h / 0 - 20 °C
2.2: 37 h / 50 °C
2.3: 1 h / 20 °C
View Scheme
15574-96-6

pizotifen

1176738-35-4

3-(4-piperidin-4-ylidene-9,10-dihydro-4H-1-thiabenzo[f]azulen-2-yl)acrylic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: triethylamine / toluene / 60 °C / Reflux
2.1: trichlorophosphate / 1,2-dichloro-ethane / 1.5 h / 0 - 20 °C
2.2: 37 h / 50 °C
2.3: 1 h / 20 °C
3.1: piperidine; hydrogenchloride / pyridine / Reflux
4.1: potassium hydroxide / isopropyl alcohol / 24 h / Reflux
4.2: pH 7 / Cooling
View Scheme
15574-96-6

pizotifen

1176739-93-7

ethyl 4-[2-(2-ethoxycarbonylvinyl)-9,10-dihydro-1-thiabenzo[f]azulen-4-ylidene]piperidine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: triethylamine / toluene / 60 °C / Reflux
2.1: trichlorophosphate / 1,2-dichloro-ethane / 1.5 h / 0 - 20 °C
2.2: 37 h / 50 °C
2.3: 1 h / 20 °C
3.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 20 °C / Inert atmosphere; Cooling
3.2: 2 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: triethylamine / toluene / 60 °C / Reflux
2: bromine / chloroform / 2 h / 20 °C
3: triethylamine; tri-ortho-toluoylphosphine / palladium diacetate / N,N-dimethyl-formamide / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: bromine / chloroform / 2 h / 0 - 20 °C
2: toluene / 6 h / Reflux
3: triethylamine; tri-ortho-toluoylphosphine / palladium diacetate / N,N-dimethyl-formamide / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: bromine / chloroform / 2 h / 0 - 20 °C
2: toluene / 6 h / Reflux
3: triethylamine / tri-ortho-toluoylphosphine; palladium diacetate / water; argon; N,N-dimethyl-formamide / 80 °C / Inert atmosphere
View Scheme
15574-96-6

pizotifen

1176739-94-8

ethyl 3-[4-(1-tert-butoxy-carbonylpiperidin-4-ylidene)-4H-1-thiabenzo[f]azulen-2-yl]-propionate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: triethylamine / toluene / 60 °C / Reflux
2.1: trichlorophosphate / 1,2-dichloro-ethane / 1.5 h / 0 - 20 °C
2.2: 37 h / 50 °C
2.3: 1 h / 20 °C
3.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 20 °C / Inert atmosphere; Cooling
3.2: 2 h / 20 °C
4.1: hydrogen bromide / acetic acid / 6 h / Reflux
5.1: acetonitrile / 20 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1: triethylamine / toluene / 60 °C / Reflux
2: bromine / chloroform / 2 h / 20 °C
3: triethylamine; tri-ortho-toluoylphosphine / palladium diacetate / N,N-dimethyl-formamide / 80 °C / Inert atmosphere
4: hydrogen bromide / acetic acid / 6 h / Reflux
5: acetonitrile / 20 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1: bromine / chloroform / 2 h / 0 - 20 °C
2: toluene / 6 h / Reflux
3: triethylamine; tri-ortho-toluoylphosphine / palladium diacetate / N,N-dimethyl-formamide / 80 °C / Inert atmosphere
4: hydrogen bromide / acetic acid / 6 h / Reflux
5: acetonitrile / 20 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: bromine / chloroform / 2 h / 0 - 20 °C
2.1: toluene / 6 h / Reflux
3.1: triethylamine / tri-ortho-toluoylphosphine; palladium diacetate / water; argon; N,N-dimethyl-formamide / 80 °C / Inert atmosphere
4.1: hydrogen bromide / acetic acid / 4 h / 120 °C
4.2: 3 h / 20 °C
View Scheme
15574-96-6

pizotifen

1262518-43-3

3-[4-(1-tert-butoxycarbonylpiperidin-4-ylidene)-4H-1-thiabenzo[f]azulen-2-yl]propionic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: triethylamine / toluene / 60 °C / Reflux
2.1: trichlorophosphate / 1,2-dichloro-ethane / 1.5 h / 0 - 20 °C
2.2: 37 h / 50 °C
2.3: 1 h / 20 °C
3.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 20 °C / Inert atmosphere; Cooling
3.2: 2 h / 20 °C
4.1: hydrogen bromide / acetic acid / 6 h / Reflux
5.1: acetonitrile / 20 h / 20 °C
6.1: sodium hydroxide; water / ethanol / 20 h
View Scheme
Multi-step reaction with 6 steps
1.1: triethylamine / toluene / 60 °C / Reflux
2.1: trichlorophosphate / 1,2-dichloro-ethane / 1.5 h / 0 - 20 °C
2.2: 37 h / 50 °C
2.3: 1 h / 20 °C
3.1: piperidine; hydrogenchloride / pyridine / Reflux
4.1: potassium hydroxide / isopropyl alcohol / 8 h / Reflux
4.2: 4 h / 60 °C
5.1: hydrogen bromide / acetic acid / 2 h / 20 - 100 °C
6.1: sodium hydroxide / isopropyl alcohol; water / 20 h / 20 °C
View Scheme
Multi-step reaction with 6 steps
1: triethylamine / toluene / 60 °C / Reflux
2: bromine / chloroform / 2 h / 20 °C
3: triethylamine; tri-ortho-toluoylphosphine / palladium diacetate / N,N-dimethyl-formamide / 80 °C / Inert atmosphere
4: hydrogen bromide / acetic acid / 6 h / Reflux
5: acetonitrile / 20 h / 20 °C
6: sodium hydroxide; water / ethanol / 20 h
View Scheme
Multi-step reaction with 6 steps
1: bromine / chloroform / 2 h / 0 - 20 °C
2: toluene / 6 h / Reflux
3: triethylamine; tri-ortho-toluoylphosphine / palladium diacetate / N,N-dimethyl-formamide / 80 °C / Inert atmosphere
4: hydrogen bromide / acetic acid / 6 h / Reflux
5: acetonitrile / 20 h / 20 °C
6: sodium hydroxide; water / ethanol / 20 h
View Scheme
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Chemistry

Product Name: Pizotifen
Molecular Structure:

Molecular Formula: C19H21NS
Molecular Weight: 295.4417
Synonyms of Pizotifen (CAS NO.15574-96-6): Pizotyline ; Pizotyline [USAN] ; 4-(9,10-Dihydro-4H-benzo(4,5)cyclohepta(1,2-b)thien-4-ylidene)-1-methylpiperidine ; BC 105 ; BRN 0753534 ; EINECS 239-632-9 ; Litec ; Piperidine, 4-(9,10-dihydro-4H-benzo(4,5)cyclohepta(1,2-b)thien-4-ylidene)-1-methyl- ; Pizotifene ; Pizotifene [INN-French] ; Pizotifeno ; Pizotifeno [INN-Spanish] ; Pizotifenum ; Pizotifenum [INN-Latin] ; Pizotyline ; Sandomigran ; Sandomygran ; UNII-0BY8440V3N                  
CAS NO: 15574-96-6
Classification Code: Anabolic ; Analgesics ; Analgesics, non-narcotic ; Antidepressant ; Antidepressive agents ; Central Nervous System Agents ; Drug / Therapeutic Agent ; Human Data ; Neurotransmitter Agents ; Peripheral Nervous System Agents ; Psychotropic Drugs ; Sensory System Agents ; Serotonin Agents ; Serotonin antagonists ; Serotonin inhibitor [specific in migraine]            
Index of Refraction: 1.63
Molar Refractivity: 90.37 cm3
Molar Volume: 253.7 cm3
Surface Tension: 47.7 dyne/cm
Density: 1.164 g/cm3
Flash Point: 217.9 °C
Enthalpy of Vaporization: 69.32 kJ/mol
Boiling Point: 436.7 °C at 760 mmHg
Vapour Pressure: 7.92E-08 mmHg at 25°C

Uses

  Pizotifen (CAS NO.15574-96-6) is mainly medical purposes that is used in vascular headache, including migraine and cluster headache prevention. It can be used for other applications, including as anti-depressants, or anxiety or social phobia treatment.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo oral 12857ug/kg/12 (12.857mg/kg) LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED" Archives of Internal Medicine. Vol. 144, Pg. 815, 1984.
rat LD50 oral 410mg/kg (410mg/kg)   Pharmacologist. Vol. 12, Pg. 297, 1970.

Safety Profile

Hazard Codes of Pizotifen (CAS NO.15574-96-6): IrritantXi
Risk Statements: 36/37/38 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-37/39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S37/39: Wear suitable gloves and eye/face protection.