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Cyproheptadine

Product Name
Cyproheptadine
CAS No.
129-03-3
Chemical Name
Cyproheptadine
Synonyms
Periactin;MK 141;Dronactin;Periactine;Periactinol;Cypoheptadine;CYPROHEPTADINE;Eiproheptadine;AKOS NCG1-0040;Cycloheptadine
CBNumber
CB7782550
Molecular Formula
C21H21N
Formula Weight
287.4
MOL File
129-03-3.mol
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Cyproheptadine Property

Melting point:
112.3-113.3°
Boiling point:
419.7°C (rough estimate)
Density 
0.9917 (rough estimate)
refractive index 
1.8240 (estimate)
storage temp. 
Store at -20°C
pka
pKa 8.87 (Uncertain)
color 
Crystals from EtOH (aq)
Water Solubility 
317.6ug/L(22.5 ºC)
CAS DataBase Reference
129-03-3(CAS DataBase Reference)
NIST Chemistry Reference
Cyproheptadine(129-03-3)
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Safety

HS Code 
29143900
Hazardous Substances Data
129-03-3(Hazardous Substances Data)
Toxicity
LD50 orl-rat: 295 mg/kg 27ZQAG -,69,72
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Cayman Chemical
Product number
19551
Product name
Cyproheptadine
Purity
≥98%
Packaging
100mg
Price
$39
Updated
2021/12/16
Cayman Chemical
Product number
19551
Product name
Cyproheptadine
Purity
≥98%
Packaging
1g
Price
$215
Updated
2021/12/16
Cayman Chemical
Product number
19551
Product name
Cyproheptadine
Purity
≥98%
Packaging
250mg
Price
$88
Updated
2021/12/16
Cayman Chemical
Product number
19551
Product name
Cyproheptadine
Purity
≥98%
Packaging
500mg
Price
$156
Updated
2021/12/16
TRC
Product number
H999760
Product name
Cycloheptadine
Packaging
250mg
Price
$550
Updated
2021/12/16
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Cyproheptadine Chemical Properties,Usage,Production

Description

Cyproheptadine has antianaphylactic activity that is associated with its ability to slow down the release of histamine and other mediators from fat cells.

Originator

Periactin,Merck Sharp and Dohme,US,1961

Uses

It is mainly used for treating bronchial asthma attacks, allergic bronchitis, rhinitis, and allergic skin reactions as well as in adjuvant therapy for anaphylactic reactions. Synonyms of this drug are periactin and vimicon.

Uses

Antihistaminic; antipruritic.

Definition

ChEBI: The product resulting from the formal oxidative coupling of position 5 of 5H-dibenzo[a,d]cycloheptene with position 4 of 1-methylpiperidine resulting in the formation of a double bond between the two fragments. t is a sedating antihistamine with antimuscarinic and calcium-channel blocking actions. It is used (particularly as the hydrochloride sesquihydrate) for the relief of allergic conditions including rhinitis, conjunctivitis due to inhalant allergens and food , urticaria and angioedema, and in pruritic skin disorders. Unlike other antihistamines, it is also a seratonin receptor antagonist, making it useful in conditions such as vascular headache and anorexia.

Manufacturing Process

(A) Preparation of 1-Methyl-4-Piperidyl-Magnesium Chloride: Magnesium turnings (5.45 g, 0.22 g-atom) were placed in a 500 ml 3-necked flask provided with a condenser, Hershberg stirrer and dropping funnel and protected with a drying tube. An atmosphere of dry nitrogen was maintained in the apparatus throughout the reaction. The magnesium was covered with 20 ml of dry tetrahydrofuran. A crystal of iodine and 1.2 g of ethyl bromide were added and after the reaction had subsided (formation of ethylmagnesium bromide) a solution of 29.4 g (0.22 mol) of 4-chloro-1-methyl-piperidine in dry tetrahydrofuran (total volume, 103 ml) was added dropwise at such a rate that gentle reflux was maintained.
The solution of 4-chloro-1-methylpiperidine in tetrahydrofuran was dried over calcium hydride at ice-bath temperature prior to use. When the addition of the halide was complete the reaction mixture was refluxed with stirring for one hour. In some subsequent experiments this period of refluxing was omitted with no deleterious result.
The solution of 4-chloro-1-methylpiperidine in tetrahydrofuran was dried over calcium hydride at ice-bath temperature prior to use. When the addition of the halide was complete the reaction mixture was refluxed with stirring for one hour. In some subsequent experiments this period of refluxing was omitted with no deleterious result.
The solvent was evaporated from the combined benzene extracts to give 33.4 g of a clear light brown resin. Crystallization from an alcohol-water mixture gave 19.5 g of 1-methyl-4-(5-hydroxy-5-dibenzo[a,e]cycloheptatrienyl)- piperidine, MP 156° to 157°C. Two recrystallizations from alcohol-water mixtures followed by two recrystallizations from benzene-hexane mixtures gave analytically pure product, MP 166.7° to 167.7°C.
(C) Preparation of 1-Methyl-4-(5-Dibenzo[a,e]Cycloheptatrienylidene)- Piperidine Hydrochloride: 1-Methyl-4-(5-hydroxy-5-dibenzo[a,e] cycloheptatrienyl)-piperidine (3.05 g, 0.01 mol) was dissolved in glacial acetic acid, 15 ml. The solution was saturated with dry hydrogen chloride with external cooling. A white solid separated. Acetic anhydride (3.07 g, 0.03 mol) was added and the mixture heated on the steam bath for one hour. The solid dissolved in the first 5 minutes of the heating period.
The reaction mixture was poured into 25 ml of water and the mixture made strongly basic with 10N sodium hydroxide solution. The mixture was extracted 3 times with 50 ml portions of benzene, the combined extracts washed with water and concentrated to a volume of approximately 50 ml. The solution was saturated with dry hydrogen chloride and the white crystalline product collected and dried. The yield of product, MP 251.6° to 252.6°C (dec.) was 2.5 g. Recrystallization from a mixture of absolute alcohol and absolute ether gave a product, MP 252.6° to 253.6°C. A sample was analyzed after drying for 7 hours at 110°C over phosphorus pentoxide in vacuo.
(D) Preparation of 1-Methyl-4-(5-Dibenzo[a,e]Cycloheptatrienylidene)- Piperidine: The hydrochloride salt, 4.3 g, was suspended in 100 ml of warm water and the mixture made strongly alkaline by the addition of 15 ml of 5% sodium hydroxide. The mixture was extracted with four 50 ml portions of benzene and the extracts dried over sodium sulfate. Evaporation of the benzene on the steam-bath at reduced pressure left 3.7 g (97%) of the base,MP 110.3° to 111.3°C. Recrystallization from a mixture of alcohol and water gave product, MP 112.3° to 113.3°C.

brand name

Periactin (Merck);Anarexal;Antegan;Apeplus;Brantina;Brantine;Carnigol;Carpantin;Ciplactin;Cipractin;Cipro n;Ciprocort;Cyrasarl;Estialim;Histatets;Ifrasarl;Kontrast u;Naidoretico;Nurdelin;Nuttriben;Oractine;Orexigen;Periactol;Perideca;Pranzo;Reparal carnitina;Siglatan;Sigloton;Sipraktin;Siprodin;Vimicon.

Therapeutic Function

Antipruritic, Antihistaminic, Appetite stimulant

World Health Organization (WHO)

Cyproheptadine, an antihistamine with anticholinergic and serotonin-antagonist properties, was introduced in 1961 for the symptomatic relief of allergy and was subsequently used as an appetite stimulant. In 1982 the drug was prohibited in Bangladesh because of its misuse as an appetite stimulant due to inappropriate promotion. Cyproheptadine remains widely available and the current marketing policy of the major manufacturer requires that it should be used as an appetite stimulant only under the supervision of a physician who should be assured that adequate food is available.

Safety Profile

Poison by ingestion, intraperitoneal, subcutaneous and intravenous routes. Experimental teratogenic and reproductive effects. When heated to decomposition it emits toxic fumes of NOx.

Synthesis

Cyproheptadine, 4-(dibenzo[a,d]cyclohepten-5-ylidene)-1-methylpiperidine (16.1.21), is synthesized by reacting 1-methyl-4-magnesiumchloropiperidine with 5H-dibeno[a,d]cycloheptene-5-one, which forms carbinol (16.1.20), the dehydration of which in an acidic medium leads to the formation of cyproheptadine (16.1.21).

Cyproheptadine Preparation Products And Raw materials

Raw materials

Preparation Products

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Cyproheptadine Suppliers

LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2127
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70
Beijing HuaMeiHuLiBiological Chemical
Tel
010-56205725
Fax
010-65763397
Email
waley188@sohu.com
Country
China
ProdList
12338
Advantage
58
Shanghai T&W Pharmaceutical Co., Ltd.
Tel
+86 21 61551611
Fax
+86 21 50676805
Country
China
ProdList
9901
Advantage
58
JinJin Le Chemical Co., Ltd
Tel
10106090
Email
jjlchem2@163.com
Country
China
ProdList
9986
Advantage
58
Aikon International Limited
Tel
025-58859352 18068836627
Fax
02557626880
Email
sales01@aikonchem.com
Country
China
ProdList
15085
Advantage
58
Conier Chem & Pharma Limited
Tel
13368167990
Email
sales@conier.com
Country
China
ProdList
2809
Advantage
58
Chengdu Saint - Kay Biotechnology Co., Ltd.
Tel
028-85157043 15882256948
Email
676046971@qq.com
Country
China
ProdList
4392
Advantage
58
Zhejiang J&C Biological Technology Co.,Limited
Tel
+1-2135480471 +1-2135480471
Email
sales@sarms4muscle.com
Country
China
ProdList
10523
Advantage
58
Hebei Lingding Biotechnology Co., Ltd.
Tel
+86-18031140164 +86-19933155420
Email
erin@hbldbiotech.com
Country
China
ProdList
878
Advantage
58
Hebei Zhanyao Biotechnology Co. Ltd
Tel
15369953316 +8615369953316
Email
admin@zhanyaobio.com
Country
China
ProdList
2136
Advantage
58
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View Lastest Price from Cyproheptadine manufacturers

Henan Tengmao Chemical Technology Co. LTD
Product
Cyproheptadine 129-03-3
Price
US $110.00-90.00/kilogram
Min. Order
1kilogram
Purity
99%
Supply Ability
10 tons/per week
Release date
2024-01-19
Hebei Lingding Biotechnology Co., Ltd.
Product
Cyproheptadine 129-03-3
Price
US $88.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
9000kg/per week
Release date
2022-01-21
Hebei Zhanyao Biotechnology Co. Ltd
Product
Cyproheptadine 129-03-3
Price
US $10.00/Kg/Bag
Min. Order
1Kg/Bag
Purity
99%
Supply Ability
20 Tons
Release date
2021-10-29

129-03-3, CyproheptadineRelated Search:


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