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Stugeron
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Name

Stugeron

 EINECS 206-064-8
CAS No. 298-57-7 Density 1.093g/cm3
PSA 6.48000 LogP 4.98280
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 N/A 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;

Article Data 26

Stugeron Synthetic route

4393-06-0

1-Phenyl-2-propen-1-ol

841-77-0

diphenylmethylpiperazine

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

100-59-4

phenylmagnesium chloride

298-57-7

cinnarizine

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

diphenylmethylpiperazine

4407-36-7

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

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%
104-54-1

3-Phenylpropenol

841-77-0

diphenylmethylpiperazine

298-57-7

cinnarizine

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

1-phenylpropadiene

841-77-0

diphenylmethylpiperazine

298-57-7

cinnarizine

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

trans-3-phenylprop-2-enyl chloride

841-77-0

diphenylmethylpiperazine

298-57-7

cinnarizine

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

styrene

50-00-0

formaldehyd

841-77-0

diphenylmethylpiperazine

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%
1522375-86-5

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

1100-88-5

benzyltriphenylphosphonium chloride

A

750512-44-8

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

B

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%
100-58-3

phenylmagnesium bromide

1-benzoyl-4-cinnamylpiperazine

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%
369-57-3

benzenediazonium tetrafluoroborate

70713-45-0

1-benzhydryl-4-allyl-piperazine

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%

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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