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Name	Pizotifen	EINECS	239-632-9
CAS No.	15574-96-6	Density	1.164g/cm³
PSA	31.48000	LogP	4.31210
Solubility	N/A	Melting Point	140-142°C
Formula	C19H21 N S	Boiling Point	436.7°Cat760mmHg
Molecular Weight	295.44	Flash Point	217.9°C
Transport Information	N/A	Appearance	N/A
Safety	26-37/39-36/37	Risk Codes	36/37/38-22-63
Molecular Structure		Hazard Symbols	Xi,Xn
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

Pizotifen Synthetic route

: 15574-96-6
pizotifen

: 1176736-68-7
4-(2-bromo-9,10-dihydro-1-thiabenzo[f]-azulen-4-ylidene)-1-methylpiperidine

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Pizotifen Chemical Properties

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

Pizotifen 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.

Pizotifen 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.

Pizotifen Safety Profile

Hazard Codes of Pizotifen (CAS NO.15574-96-6): Irritant Xi
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.

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