Product Name

  • Name

    Stugeron

  • EINECS 206-064-8
  • CAS No. 298-57-7
  • Article Data26
  • CAS DataBase
  • Density 1.093g/cm3
  • Solubility 750 mg/L at 25 °C in water
  • Melting Point 117-120oC
  • Formula C26H28N2
  • Boiling Point 509.2oC at 760mmHg
  • Molecular Weight 368.522
  • Flash Point 229.8oC
  • Transport Information
  • Appearance white powder
  • Safety 22-24/25-36-26
  • Risk Codes 20/22-36/37/38-42/43
  • Molecular Structure Molecular Structure of 298-57-7 (Stugeron)
  • Hazard Symbols HarmfulXn
  • Synonyms Piperazine,1-cinnamyl-4-(diphenylmethyl)- (6CI,7CI,8CI);1-(3-Phenylallyl)-4-(diphenylmethyl)piperazine;1-Cinnamyl-4-(diphenylmethyl)piperazine;1-Diphenylmethyl-4-cinnamoylpiperazine;516MD;Aplactan;Apotomin;Carecin;Cerepar;Cinarizine;Cinnacet;Cinnipirine;Denapol;Dimitronal;Folcodal;Glanil;Ixterol;Labyrin;Marisan;Mitronal;Olamin;Sepan;Spaderizine;Stutgeron;Toliman;
  • PSA 6.48000
  • LogP 4.98280

Synthetic route

1-Phenyl-2-propen-1-ol
4393-06-0

1-Phenyl-2-propen-1-ol

diphenylmethylpiperazine
841-77-0

diphenylmethylpiperazine

cinnarizine
298-57-7

cinnarizine

Conditions
ConditionsYield
With Pd(xantphos)(MeCN)2(OTf)2 In isopropyl alcohol at 20℃; for 12h; Inert atmosphere;95%
1-[(2E)-3-chloroprop-2-en-1-yl]-4-(diphenylmethyl)piperazine

1-[(2E)-3-chloroprop-2-en-1-yl]-4-(diphenylmethyl)piperazine

phenylmagnesium chloride
100-59-4

phenylmagnesium chloride

cinnarizine
298-57-7

cinnarizine

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; iron(III)-acetylacetonate In tetrahydrofuran at 0 - 20℃; Inert atmosphere;90%
diphenylmethylpiperazine
841-77-0

diphenylmethylpiperazine

(2E)-3-phenyl-2-propen-1-ol
4407-36-7

(2E)-3-phenyl-2-propen-1-ol

cinnarizine
298-57-7

cinnarizine

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(η3-allyl-μ-chloropalladium(II)) In methanol at 20℃; for 12h; Temperature; Inert atmosphere;90%
3-Phenylpropenol
104-54-1

3-Phenylpropenol

diphenylmethylpiperazine
841-77-0

diphenylmethylpiperazine

cinnarizine
298-57-7

cinnarizine

Conditions
ConditionsYield
In o-xylene at 150℃; for 30h; Inert atmosphere; Sealed tube;90%
1-phenylpropadiene
2327-99-3

1-phenylpropadiene

diphenylmethylpiperazine
841-77-0

diphenylmethylpiperazine

cinnarizine
298-57-7

cinnarizine

Conditions
ConditionsYield
With [3IPtBuPd(allyl)]OTf In benzene-d6 at 25℃; for 3h; Glovebox; Inert atmosphere; Sealed tube;82%
trans-3-phenylprop-2-enyl chloride
21087-29-6

trans-3-phenylprop-2-enyl chloride

diphenylmethylpiperazine
841-77-0

diphenylmethylpiperazine

cinnarizine
298-57-7

cinnarizine

Conditions
ConditionsYield
In methanol at 100℃; under 5171.62 Torr; for 0.5h; Flow reactor;82%
styrene
292638-84-7

styrene

formaldehyd
50-00-0

formaldehyd

diphenylmethylpiperazine
841-77-0

diphenylmethylpiperazine

cinnarizine
298-57-7

cinnarizine

Conditions
ConditionsYield
With dichloro[9,9-dimethyl-4,5- bis(diphenylphosphino)xanthene]palladium (II) In methanol at 110℃; for 36h; Inert atmosphere; diastereoselective reaction;75%
...Expand
1-benzhydryl-4-(2-acetaldehyde)piperazine
1522375-86-5

1-benzhydryl-4-(2-acetaldehyde)piperazine

benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

A

(Z)-1-(diphenylmethyl)-4-cinnamylpiperazine
750512-44-8

(Z)-1-(diphenylmethyl)-4-cinnamylpiperazine

B

cinnarizine
298-57-7

cinnarizine

Conditions
ConditionsYield
With potassium tert-butylate In dichloromethane at 5℃; Wittig Olefination; Inert atmosphere; stereoselective reaction;A 72.8%
B 8.8%
...Expand
phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

1-benzoyl-4-cinnamylpiperazine

1-benzoyl-4-cinnamylpiperazine

cinnarizine
298-57-7

cinnarizine

Conditions
ConditionsYield
Stage #1: 1-benzoyl-4-cinnamylpiperazine With bis(triphenylphosphine)carbonyliridium(I) chloride; 1,1,3,3-Tetramethyldisiloxane In dichloromethane at 20℃; for 0.333333h;
Stage #2: phenylmagnesium bromide at -78 - 20℃; for 4h;		67%
benzenediazonium tetrafluoroborate
369-57-3

benzenediazonium tetrafluoroborate

1-benzhydryl-4-allyl-piperazine
70713-45-0

1-benzhydryl-4-allyl-piperazine

cinnarizine
298-57-7

cinnarizine

Conditions
ConditionsYield
With bathophenanthroline; bis(dibenzylideneacetone)-palladium(0) In N,N-dimethyl-formamide at 20℃; Heck Reaction; Inert atmosphere; stereoselective reaction;65%
bromobenzene
108-86-1

bromobenzene

diphenylmethylpiperazine
841-77-0

diphenylmethylpiperazine

1-acetoxy-5-methyl-3,7-dioxo-9-vinyl-2,8-dioxa-5-aza-1-borabicyclo[3.3.1]nonan-5-ium-1-uide

1-acetoxy-5-methyl-3,7-dioxo-9-vinyl-2,8-dioxa-5-aza-1-borabicyclo[3.3.1]nonan-5-ium-1-uide

cinnarizine
298-57-7

cinnarizine

Conditions
ConditionsYield
With potassium phosphate; bis(η3-allyl-μ-chloropalladium(II)); triphenylphosphine In tetrahydrofuran; water at 80℃; for 16h; Sealed tube; Inert atmosphere; Schlenk technique;51%
...Expand
diphenylmethylpiperazine
841-77-0

diphenylmethylpiperazine

A

(Z)-1-(diphenylmethyl)-4-cinnamylpiperazine
750512-44-8

(Z)-1-(diphenylmethyl)-4-cinnamylpiperazine

B

cinnarizine
298-57-7

cinnarizine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium carbonate; potassium iodide / 85 - 90 °C
2: hydrogen bromide; water / 20 °C
3: potassium tert-butylate / dichloromethane / 5 °C / Inert atmosphere
View Scheme
benzophenone
119-61-9

benzophenone

A

(Z)-1-(diphenylmethyl)-4-cinnamylpiperazine
750512-44-8

(Z)-1-(diphenylmethyl)-4-cinnamylpiperazine

B

cinnarizine
298-57-7

cinnarizine

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: sodium tetrahydroborate / methanol / 20 °C
2: tetrabutylammomium bromide; hydrogenchloride / water; toluene / 40 - 45 °C
3: toluene / 60 - 100 °C
4: potassium carbonate; potassium iodide / 85 - 90 °C
5: hydrogen bromide; water / 20 °C
6: potassium tert-butylate / dichloromethane / 5 °C / Inert atmosphere
View Scheme
1-(diphenylmethyl)-4-(2,2-dimethoxyethyl)piperazine
1522375-83-2

1-(diphenylmethyl)-4-(2,2-dimethoxyethyl)piperazine

A

(Z)-1-(diphenylmethyl)-4-cinnamylpiperazine
750512-44-8

(Z)-1-(diphenylmethyl)-4-cinnamylpiperazine

B

cinnarizine
298-57-7

cinnarizine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogen bromide; water / 20 °C
2: potassium tert-butylate / dichloromethane / 5 °C / Inert atmosphere
View Scheme
1,1-Diphenylmethanol
91-01-0

1,1-Diphenylmethanol

A

(Z)-1-(diphenylmethyl)-4-cinnamylpiperazine
750512-44-8

(Z)-1-(diphenylmethyl)-4-cinnamylpiperazine

B

cinnarizine
298-57-7

cinnarizine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: tetrabutylammomium bromide; hydrogenchloride / water; toluene / 40 - 45 °C
2: toluene / 60 - 100 °C
3: potassium carbonate; potassium iodide / 85 - 90 °C
4: hydrogen bromide; water / 20 °C
5: potassium tert-butylate / dichloromethane / 5 °C / Inert atmosphere
View Scheme
diphenylchloromethane
90-99-3

diphenylchloromethane

A

(Z)-1-(diphenylmethyl)-4-cinnamylpiperazine
750512-44-8

(Z)-1-(diphenylmethyl)-4-cinnamylpiperazine

B

cinnarizine
298-57-7

cinnarizine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: toluene / 60 - 100 °C
2: potassium carbonate; potassium iodide / 85 - 90 °C
3: hydrogen bromide; water / 20 °C
4: potassium tert-butylate / dichloromethane / 5 °C / Inert atmosphere
View Scheme
1,1-Diphenylmethanol
91-01-0

1,1-Diphenylmethanol

cinnarizine
298-57-7

cinnarizine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride / water / 0.25 h / 120 °C / 5171.62 Torr / Flow reactor
2: acetone; tetrahydrofuran / 0.75 h / 150 °C / 12929 Torr / Flow reactor
3: methanol / 0.5 h / 100 °C / 5171.62 Torr / Flow reactor
View Scheme
Multi-step reaction with 3 steps
1: hydrogenchloride / water; acetone / 0.17 h / 100 °C / 5171.62 Torr / Flow reactor
2: acetone; tetrahydrofuran / 0.75 h / 150 °C / 12929 Torr / Flow reactor
3: methanol / 0.5 h / 100 °C / 5171.62 Torr / Flow reactor
View Scheme
diphenylchloromethane
90-99-3

diphenylchloromethane

cinnarizine
298-57-7

cinnarizine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetone; tetrahydrofuran / 0.75 h / 150 °C / 12929 Torr / Flow reactor
2: methanol / 0.5 h / 100 °C / 5171.62 Torr / Flow reactor
View Scheme
(2E)-3-phenyl-2-propen-1-ol
4407-36-7

(2E)-3-phenyl-2-propen-1-ol

cinnarizine
298-57-7

cinnarizine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / water / 0.25 h / 120 °C / 5171.62 Torr / Flow reactor
2: methanol / 0.5 h / 100 °C / 5171.62 Torr / Flow reactor
View Scheme
Multi-step reaction with 2 steps
1: hydrogenchloride / water / 15 h / 60 °C / 5171.62 Torr / Flow reactor
2: methanol / 0.5 h / 100 °C / 5171.62 Torr / Flow reactor
View Scheme
allylbenzene
300-57-2

allylbenzene

cinnarizine
298-57-7

cinnarizine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: bromine / chloroform / 0.17 h / 0 °C
2: 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium iodide / dimethyl sulfoxide / 2 h / 22 °C / Sealed tube
View Scheme
(2,3-dibromopropyl)benzene
1586-98-7

(2,3-dibromopropyl)benzene

diphenylmethylpiperazine
841-77-0

diphenylmethylpiperazine

cinnarizine
298-57-7

cinnarizine

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium iodide In dimethyl sulfoxide at 22℃; for 2h; Sealed tube; stereoselective reaction;58 mg
diphenylmethylpiperazine
841-77-0

diphenylmethylpiperazine

3-phenyl-propenal
104-55-2

3-phenyl-propenal

cinnarizine
298-57-7

cinnarizine

Conditions
ConditionsYield
With formic acid; 4Zn(2+)*4C30H23N7O3(2-)*4BF4(1-)*2C2H3N*4H(1+); sodium cyanoborohydride; triethylamine In water; acetonitrile at 24.84℃; for 12h; pH=8.5; Inert atmosphere; Irradiation;71 %Spectr.
cinnarizine
298-57-7

cinnarizine

cinnarizine hydrochloride
880764-36-3

cinnarizine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether at 20℃; for 4h;99%
dichloro-acetic acid
79-43-6

dichloro-acetic acid

cinnarizine
298-57-7

cinnarizine

cinnarizine dichloroacetate

cinnarizine dichloroacetate

Conditions
ConditionsYield
In methanol at 20℃; for 1h;99%
decylsulfate ammonium salt
13177-52-1

decylsulfate ammonium salt

cinnarizine
298-57-7

cinnarizine

cinnarizine 1-decyl sulfate

cinnarizine 1-decyl sulfate

Conditions
ConditionsYield
Stage #1: cinnarizine With hydrogenchloride In diethyl ether
Stage #2: decylsulfate ammonium salt In chloroform for 48h; Reflux;		96%
trans-1,2-dichloroethylene
156-60-5

trans-1,2-dichloroethylene

cinnarizine
298-57-7

cinnarizine

1-[(2E)-3-chloroprop-2-en-1-yl]-4-(diphenylmethyl)piperazine

1-[(2E)-3-chloroprop-2-en-1-yl]-4-(diphenylmethyl)piperazine

Conditions
ConditionsYield
With C56H65F5MoN2O In toluene; paraffin oil at 50℃; for 4h; diastereoselective reaction;95%
cinnarizine
298-57-7

cinnarizine

benzene
71-43-2

benzene

1-benzhydryl-4-(3,3-diphenyl-propyl)-piperazine
48230-16-6

1-benzhydryl-4-(3,3-diphenyl-propyl)-piperazine

Conditions
ConditionsYield
With trifluorormethanesulfonic acid at 25℃; for 3h;75%
cinnarizine
298-57-7

cinnarizine

β‐cyclodextrin
7585-39-9

β‐cyclodextrin

cinnarizin * β-cyclodextrin complex
89965-71-9, 97413-12-2, 97453-61-7, 107641-77-0

cinnarizin * β-cyclodextrin complex

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide In water 2.) pH 11.0; 3.) pH 7.0;
cinnarizine
298-57-7

cinnarizine

cyclomaltooctaose
17465-86-0

cyclomaltooctaose

cinnarizin * γ-cyclodextrin complex
89971-15-3

cinnarizin * γ-cyclodextrin complex

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide In water 2.) pH 11.0; 3.) pH 7.0;
C10H15Cl3N2O4S
1439889-63-0

C10H15Cl3N2O4S

cinnarizine
298-57-7

cinnarizine

A

C36H39Cl3N4O4S
1439890-20-6

C36H39Cl3N4O4S

B

C36H39Cl3N4O4S
1439890-25-1

C36H39Cl3N4O4S

Conditions
ConditionsYield
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; bis(tertbutylcarbonyloxy)iodobenzene In benzene at 23℃; for 0.5h; Inert atmosphere; Overall yield = 21 %;A n/a
B n/a
...Expand
cinnarizine
298-57-7

cinnarizine

C25H29N3O

C25H29N3O

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: C56H65F5MoN2O / paraffin oil; toluene / 4 h / 50 °C
2: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; cesium fluoride; palladium diacetate / isopropyl alcohol / 12 h / 85 °C
View Scheme
cinnarizine
298-57-7

cinnarizine

C25H25F2N3

C25H25F2N3

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: C56H65F5MoN2O / paraffin oil; toluene / 4 h / 50 °C
2: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; cesium fluoride; palladium diacetate / isopropyl alcohol / 12 h / 85 °C
View Scheme

Stugeron History

 Cinnarizine (298-57-7) was first synthesized by Janssen Pharmaceutica in 1955.

Stugeron Specification

This chemical is called Cinnarizine, and its IUPAC name is 1-benzhydryl-4-(3-phenylprop-2-enyl)piperazine. With the molecular formula of C26H28N2, its classification codes are Antihistaminic; Calcium channel blockers; Cardiovascular Agents; Drug / Therapeutic Agent; Histamine Agents; Histamine Antagonists; Histamine H1 antagonists; Human Data; Membrane Transport Modulators; Neurotransmitter Agents; Reproductive Effect. The CAS registry number of this chemical is 298-57-7. Additionally, its product categories are Miscellaneous Natural Products; Intermediates & Fine Chemicals; Pharmaceuticals; Histamine Receptor. What's more, it's calcium channel blocker for antiallergic.

Other characteristics of the Cinnarizine can be summarised as followings: (1)XLogP3: 5.8; (2)H-Bond Donor: 0; (3)H-Bond Acceptor: 2; (4)Rotatable Bond Count: 6; (5)Exact Mass: 368.225249; (6)MonoIsotopic Mass: 368.225249; (7)Topological Polar Surface Area: 6.5; (8)Heavy Atom Count: 28; (9)Formal Charge: 0; (10)Complexity: 429; (11)Isotope Atom Count: 0; (12)Undefined Bond StereoCenter Count: 1; (13)Covalently-Bonded Unit Count: 1; (14)Feature 3D Cation Count: 2; (15)Feature 3D Ring Count: 4; (16)Effective Rotor Count: 7.2; (17)Conformer Sampling RMSD: 0.8; (18)CID Conformer Count: 44.

Uses of this chemical: The Cinnarizine could react with benzene to obtain the 1-benzhydryl-4-(3,3-diphenyl-propyl)-piperazine. This reaction needs the reagent of triflic acid. The yield is 75 %. In addition, this reaction should be taken for 3 hours at the temperature of 25 °C.

The Cinnarizine could react with benzene1-benzhydryl-4-(3,3-diphenyl-propyl)-piperazine

When you are using this chemical, please be cautious about it as the following: This chemical is irritating / harmful to eyes, respiratory system and skin. Do not breathe dust. You should wear suitable protective clothing to avoid contacting with skin and eyes. In case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
1. InChI: InChI=1/C26H28N2/c1-4-11-23(12-5-1)13-10-18-27-19-21-28(22-20-27)26(24-14-6-2-7-15-24)25-16-8-3-9-17-25/h1-17,26H,18-22H2/b13-10+
2.Smiles: c1ccc(cc1)\C=C\CN1CCN(CC1)C(c1ccccc1)c1ccccc1

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intraperitoneal > 500mg/kg (500mg/kg)   Drugs in Japan Vol. -, Pg. 515, 1990.
dog LD50 oral > 500mg/kg (500mg/kg)   Drugs in Japan Vol. -, Pg. 515, 1990.
dog LD50 subcutaneous > 500mg/kg (500mg/kg)   Drugs in Japan Vol. -, Pg. 515, 1990.
mouse LD50 intraperitoneal 730mg/kg (730mg/kg)   Medicamentos de Actualidad. Vol. 21, Pg. 443, 1985.
mouse LD50 intravenous 22mg/kg (22mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

LUNGS, THORAX, OR RESPIRATION: CYANOSIS		 Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 1735, 1982.
mouse LD50 oral > 4500mg/kg (4500mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SKIN AND APPENDAGES (SKIN): HAIR: OTHER		 Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 1735, 1982.
mouse LD50 subcutaneous > 2gm/kg (2000mg/kg)   Drugs in Japan Vol. -, Pg. 515, 1990.
rat LD50 intraperitoneal 1050mg/kg (1050mg/kg)   Medicamentos de Actualidad. Vol. 21, Pg. 443, 1985.
rat LD50 intravenous 24mg/kg (24mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: CYANOSIS		 Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 1735, 1982.
rat LD50 oral > 6500mg/kg (6500mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SKIN AND APPENDAGES (SKIN): HAIR: OTHER		 Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 1735, 1982.
rat LD50 subcutaneous > 2gm/kg (2000mg/kg)   Drugs in Japan Vol. -, Pg. 515, 1990.
women TDLo oral 252mg/kg/12W- (252mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE" British Journal of Dermatology. Vol. 112, Pg. 607, 1985.
women TDLo oral 22500mg/kg/22 (22500mg/kg)   Annals of Pharmacotherpy. Vol. 26, Pg. 928, 1992.

 

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