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CYPROHEPTADINE HYDROCHLORIDE

Product Name
CYPROHEPTADINE HYDROCHLORIDE
CAS No.
969-33-5
Chemical Name
CYPROHEPTADINE HYDROCHLORIDE
Synonyms
CYPROHEPTADINE HCL;4-(5H-DIBENZO[A,D]CYCLOHEPTEN-5-YLIDINE)-METHYLPIPERIDINE HYDROCHLORIDE;nuran;peritol;ANAREXOL;periactinsyrup;Cycloheptadine HCl;CYPROHEPTADINE HCL BP;periactinhydrochloride;periactinolhydrochloride
CBNumber
CB2698687
Molecular Formula
C21H21N.ClH
Formula Weight
323.86
MOL File
969-33-5.mol
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CYPROHEPTADINE HYDROCHLORIDE Property

Melting point:
254-256.5 °C(Solv: ethanol (64-17-5); ethyl ether (60-29-7))
storage temp. 
Inert atmosphere,Room Temperature
solubility 
ethanol: soluble
form 
solid
color 
Crystals from EtOH/Et2O
Water Solubility 
Soluble in water (15mM)
Stability:
Hygroscopic
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Safety

Hazard Codes 
Xn
Risk Statements 
22-36/37/38
Safety Statements 
26-36
RIDADR 
UN 2811 6.1/PG 3
WGK Germany 
3
RTECS 
TM7050000
HazardClass 
6.1(b)
PackingGroup 
III
Toxicity
LD50 orl-rat: 295 mg/kg DRUGAY 6,340,82
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

H361Suspected of damaging fertility or the unborn child

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P281Use personal protective equipment as required.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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

P308+P313IF exposed or concerned: Get medical advice/attention.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

AK Scientific
Product number
J53419
Product name
CyproheptadineHCl
Packaging
5g
Price
$47.2
Updated
2021/12/16
ApexBio Technology
Product number
B3309
Product name
Cyproheptadine hydrochloride
Packaging
10mM(in 1mL DMSO)
Price
$50
Updated
2021/12/16
Biosynth Carbosynth
Product number
FC61445
Product name
Cyproheptadine hydrochloride
Packaging
100mg
Price
$50
Updated
2021/12/16
ApexBio Technology
Product number
B3309
Product name
Cyproheptadine hydrochloride
Packaging
1unit
Price
$28
Updated
2021/12/16
AK Scientific
Product number
M230
Product name
CyproheptadineHCl
Packaging
1g
Price
$29
Updated
2021/12/16
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CYPROHEPTADINE HYDROCHLORIDE Chemical Properties,Usage,Production

Originator

Periactin,Merck Sharp and Dohme,US,1961

Uses

Antipruritic;5-HT antagonist

Uses

Cyproheptadine hydrochloride is an antihistamine in which antiserotonin activity has been demonstrated both in vivo and in vitro. As yet, however, there is no evidence that this action contributes to clinical therapeutic effects. Anticholinergic and sedative effects are observed. Cyproheptadine may be more effective than other H1 blockers in the management of cold urticaria.

Definition

ChEBI: The hydrochloride salt of cyproheptadine. Note that the drug named cyproheptadine hydrochloride generally refers to cyproheptadine hydrochloride sesquihydrate.

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).

Therapeutic Function

Antipruritic, Antihistaminic, Appetite stimulant

General Description

Cyproheptadinehydrochloride, 4-(5H-dibenzo-[a,d]-cyclohepten-5-ylidine)-1-methylpiperidine hydrochloride sesquihydrate(Periactin), is slightly soluble in water and sparingly solublein alcohol.
Cyproheptadine possesses both antihistamine and antiserotoninactivity and is used as an antipruritic agent. It isindicated for the treatment of hypersensitivity reactions,perennial, and seasonal allergic rhinitis; vasomotor rhinitis;allergic conjunctivitis, uncomplicated allergic skin manifestationsof urticaria and angioedema; amelioration of allergicreactions to blood or plasma; and cold urticaria. It is alsoused off-label for nightmares associated with posttraumaticstress disorder (PTSD), prevention of migraine, suppressionof vascular headaches, and appetite stimulation. Sedation isthe most prominent side effect, and this is usually brief, disappearingafter 3 or 4 days of treatment.

Biological Activity

Non-selective 5HT 2 antagonist, migraine prophylactic.

Safety Profile

Poison by ingestion and intraperitoneal routes. Human systemic effects by ingestion: jaundice, liver function tests impaired, gastrointestinal effects. An experimental teratogen. Experimental reproductive effects. Human mutation data reported. Whenheated

Drug interactions

Potentially hazardous interactions with other drugs
Analgesics: sedative properties increased with opioid analgesics.

Metabolism

Undergoes almost complete metabolism in the liver. The main metabolite found in humans is a quaternary ammonium glucuronide conjugate of cyproheptadine. 40% is excreted in the urine mainly as metabolites and 2-20% via the faeces.

storage

Room temperature

References

[1] levine b, green-johnson d, hogan s, smialek je. a cyproheptadine fatality. j anal toxicol. 1998 jan-feb;22(1):72-4.
[2] lin oa, karim za, vemana hp, espinosa ev, khasawneh ft. the antidepressant 5-ht2a receptor antagonists pizotifen and cyproheptadine inhibit serotonin-enhanced platelet function. plos one. 2014 jan 23;9(1):e87026.

CYPROHEPTADINE HYDROCHLORIDE Preparation Products And Raw materials

Raw materials

Preparation Products

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CYPROHEPTADINE HYDROCHLORIDE Suppliers

SIGMA-RBI
Tel
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Switzerland
ProdList
6896
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View Lastest Price from CYPROHEPTADINE HYDROCHLORIDE manufacturers

Hebei Zhuanglai Chemical Trading Co Ltd
Product
Cycloheptadine HCl 969-33-5
Price
US $150.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
500kg
Release date
2024-11-25
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Cyproheptadine hydrochloride 969-33-5
Price
US $0.00-0.00/Kg/Drum
Min. Order
1KG
Purity
98.5%-100.5%; USP
Supply Ability
500kg
Release date
2021-09-11
Hebei Weibang Biotechnology Co., Ltd
Product
CYPROHEPTADINE HYDROCHLORIDE 969-33-5
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2024-11-28

969-33-5, CYPROHEPTADINE HYDROCHLORIDERelated Search:


  • CYPROHEPTADINE HYDROCHLORIDE(GRP B SL NO.1124)
  • Cycloheptadine Hydrochloride
  • 1-methyl-4-(5-dibenzo(a,e)cycloheptatrienylidene)piperidinehydrochloride
  • 4-(5-dibenzo(a,e)cycloheptatrienylidene)piperidinehydrochloride
  • 4-(5h-dibenzo(a,d)cyclohepten-5-ylidene)-1-methyl-piperidinhydrochloride
  • cyproheptadienehydrochloride
  • nuran
  • 4-(5H-DIBENZO[A,D]CYCLOHEPTEN-5-YLIDINE)-METHYLPIPERIDINE HYDROCHLORIDE
  • CYPROHEPTADINE HCL
  • CyproheptadineHclCyproheptadineHclBp
  • CYPROHEPTADINEHYDROCHLORIDE(ANHYDROUS)
  • ANAREXOL
  • CYPROHEPTADINE HCL BP
  • Cyproheptadine hydrochloride (Periactin)
  • Cyproheptadine hydrochloride
  • periactinhydrochloride
  • periactinolhydrochloride
  • periactinsyrup
  • peritol
  • Cyproheptadine hydrochloride,CYPROHEPTADINE HCL, periactinolhydrochloride
  • 4-(5H-dibenzo[a,d][7]annulen-5-ylidene)-1-methylpiperidine hydrochloride
  • Cyproheptadine hydrochloride USP/EP/BP
  • Cyproheptadine hydrochloride USP/EP/BP USP/EP/BP
  • 1-Methyl-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-piperidine hydrochloride
  • Cyproheptadinhydrochlorid
  • Cyheptadine hydrochloride
  • Piperidine, 4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-methyl-, hydrochloride (1:1)
  • Cycloheptadine HCl
  • 969-33-5
  • 354-29-4
  • C21H21NHCl1H2O
  • C21H21NClH
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  • Heterocyclic Building Blocks
  • Piperidines
  • Serotonin receptor
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