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Cyproheptadine hydrochloride

CAS：41354-29-4
MW:341.88
MF：C21H24ClNO

Cyproheptadine hydrochloride, with the chemical formula C21H21ClN2O2 and CAS registry number 41354-29-4, is a compound commonly used as an antihistamine and serotonin antagonist. It is primarily used to treat allergic reactions, such as hay fever and hives, by blocking the effects of histamine in the body. Cyproheptadine hydrochloride is also used to stimulate appetite in individuals with conditions such as anorexia nervosa and cystic fibrosis. This white crystalline powder is known for its ability to bind to various receptors in the body, including histamine H1 receptors, serotonin 5-HT2 receptors, and muscarinic acetylcholine receptors. It is typically administered orally and may cause side effects such as drowsiness, dry mouth, and constipation. Cyproheptadine hydrochloride is an important compound in the field of pharmacology and plays a significant role in managing allergic reactions and appetite stimulation.

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Names and ldentifier
Properties
Use and Manufacturing
Safety and Handling
Msds
NMR Spectrum
Other Information
Computational chemical data
Related Questions
Realated Product Infomation

1. Names and Identifiers

1.1 Name: Cyproheptadine hydrochloride

1.2 Synonyms: 4-(5H-Dibenzo[a,d][7]annulen-5-ylidene)-1-methylpiperidine hydrochloride hydrate (2:2:3); 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-methyl-piperidine hydrochloride hydrate; 4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-methyl-piperidine,hydrochloride, hydrate (2:2:3); Cyproheptadine (hydrochloride sesquihydrate); CYPROHEPTADINE HCI; Cyproheptadine hydrochlorid; Cyproheptadine hydrochloride hydrate(2:2:3); Cyproheptadine hydrochloride sesquihydrate; EINECS 213-535-1; Hydrochloride sesquihydrate; MFCD00012538; Periactin; Piperidine (4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-methyl; Piperidine, 4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-methyl-, hydrochloride, hydrate (2:2:3); Piperidine,4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-Methyl-, hydrochloride, hydrate(2:2:3);

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1.3 CAS No.: 41354-29-4

1.4 CID: 11954233

1.5 EINECS: 623-762-1

1.6 Molecular Formula: C21H24ClNO

1.7 Inchi: InChI=1S/C21H21N.ClH.H2O/c1-22-14-12-18(13-15-22)21-19-8-4-2-6-16(19)10-11-17-7-3-5-9-20(17)21;;/h2-11H,12-15H2,1H3;1H;1H2

1.8 InChkey: PFQPCBUPUOPHGM-UHFFFAOYSA-N

1.9 Canonical Smiles: O.Cl.CN1CCC(CC1)=C1C2=CC=CC=C2C=CC2=C1C=CC=C2

1.10 Isomers Smiles: CN1CCC(=C2C3=CC=CC=C3C=CC4=CC=CC=C42)CC1.CN1CCC(=C2C3=CC=CC=C3C=CC4=CC=CC=C42)CC1.O.O.O.Cl.Cl

2. Properties

2.1 Solubility: ethanol: soluble

2.2 Λmax: 285nm(0.05mol/L H2SO4)(lit.)

2.3 Appearance: white to slightly yellow

2.4 Chemical Properties: White or slightly yellow, crystalline powder.

2.5 Color/Form: white to slightly yellow

2.6 Water Solubility: ethanol: soluble

2.7 StorageTemp: Inert atmosphere,Room Temperature

3. Use and Manufacturing

3.1 Definition: ChEBI: The sesquihydrate of cyproheptadine hydrochloride. Note that the drug named cyproheptadine hydrochloride generally refers to cyproheptadine hydrochloride sesquihydrate. A sedating antihistamine with antimuscarinic and calcium-channel blocking actions, it i used for the relief of allergic conditions including rhinitis, conjunctivitis due to inhalant allergens and foods, urticaria and angioedema, and in pruritic skin disorders. Unlike other antihistamines, it is also a seratonin receptor antagonist, making ituseful in conditions such as vascular headache and anorexia.

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3.2 Description

Cyproheptadine hydrochloride is a chemical compound with the CAS number 41354-29-4. It is a white crystalline powder with no distinct odor. The molecular formula of cyproheptadine hydrochloride is C21H22ClN. It is soluble in water and ethanol. When handling this compound, it is important to follow safety precautions as it may cause irritation to the skin and eyes. Ingestion of cyproheptadine hydrochloride may lead to illness. It is essential to prevent its release into the environment as it can be harmful to the ecosystem.

Applicable Fields

Pharmaceuticals: Cyproheptadine hydrochloride is primarily used in the field of pharmaceuticals. It is an antihistamine and antiserotonergic agent. Its purpose in this field is to treat various conditions such as allergies, itching, and serotonin syndrome. The mechanism of action of cyproheptadine hydrochloride involves blocking the effects of histamine and serotonin in the body, thereby alleviating symptoms associated with these conditions.

Storage

Conditions: Store in a cool and dry place.

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3.3 GHS Classification: Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 61 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H301 (60.66%): Toxic if swallowed [Danger Acute toxicity, oral]
H302 (39.34%): Harmful if swallowed [Warning Acute toxicity, oral]
H315 (39.34%): Causes skin irritation [Warning Skin corrosion/irritation]
H318 (55.74%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
H319 (39.34%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (39.34%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
H336 (55.74%): May cause drowsiness or dizziness [Warning Specific target organ toxicity, single exposure; Narcotic effects]
H361 (55.74%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
H400 (55.74%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]
H410 (55.74%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P201, P202, P261, P264, P270, P271, P273, P280, P281, P301+P310, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P312, P321, P330, P332+P313, P337+P313, P362, P391, P403+P233, P405, and P501

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3.4 Usage: Anticoagulant, anti-allergic drugs. It can be used for urticaria, eczema, and allergic contact dermatitis, skin itching and other allergic reactions. It can also be used for Cushing's diseases and acromegaly.

4. Safety and Handling

4.1 Safety: Hazard Codes:Xn
Risk Statements:22-36/37/38
22:Harmful if swallowed
36/37/38:Irritating to eyes, respiratory system and skin
Safety Statements:26-36
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:Wear suitable protective clothing
RIDADR:UN 2811 6.1/PG 3
WGK Germany:3

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4.2 Specification: Safety Statements:26-36
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:Wear suitable protective clothing

4.3 Toxicity: Organic Compound; Amine; Drug; Food Toxin; Gastrointestinal Agent; Serotonin Antagonist; Anti-Allergic Agent; Histamine H1 Antagonist; Antihistamine Derivative; Antipruritic; Metabolite; Synthetic Compound

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 3

Serious eye damage, Category 1

Specific target organ toxicity \u2013 single exposure, Category 3

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H301 Toxic if swallowed H318 Causes serious eye damage H336 May cause drowsiness or dizziness H410 Very toxic to aquatic life with long lasting effects
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area. P273 Avoid release to the environment.
Response	P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026 P321 Specific treatment (see ... on this label). P330 Rinse mouth. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P310 Immediately call a POISON CENTER/doctor/\u2026 P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell. P391 Collect spillage.
Storage	P405 Store locked up. P403+P233 Store in a well-ventilated place. Keep container tightly closed.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

7. Computed Properties

Molecular Weight：341.88g/mol
Molecular Formula：C₂₁H₂₄ClNO
Compound Is Canonicalized：True
XLogP3-AA：700.3198488
Monoisotopic Mass：700.3198488
Complexity：423
Rotatable Bond Count：0
Hydrogen Bond Donor Count：5
Hydrogen Bond Acceptor Count：5
Topological Polar Surface Area：9.5
Heavy Atom Count：：49
Defined Atom Stereocenter Count：0
Undefined Atom Stereocenter Count：0
Defined Bond Stereocenter Count：0
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：7
CACTVS Substructure Key Fingerprint：AAADcfB/MAAGAAAAAAAAAAAAAAAAAAAAAAA8eMGCBAgAAAABVAAAHAAACAAADADBGAQyAIMAAACAAiBCAAACAAAgAAAIiAAIAIgIICKAkRCEIAAggACIiAcQgMAOgAAAAAAQAAAAAAAAACAAAAAAAAAAAA==

8.Other Information

Merck: 14,2773

Antihistamines: Cyproheptadine hydrochloride is a kind of pipecolic antihistamines,it can compete with histamine released from the organization for H1 receptor on effector cells , thereby it can prevent the onset of an allergic reaction, and release histamine-induced spasm and congestion effects, this product has a strong H1 receptor antagonism, its anti-histamine effect is stronger than chlorpheniramine, promethazine . There are mild to moderate anti-serotonin effects and anticholinergic effects. In addition, there is a stimulate appetite effect, and weight gains after a certain time.
Clinically cyproheptadine hydrochloride is mainly used for acute and chronic urticaria (especially it has a good effect on cold urticaria ), papular urticaria, angioedema, atopic eczema, contact dermatitis, food allergy, drug allergy, allergic rhinitis, hay fever, allergic conjunctivitis, allergic to insect stings and migraine. It has some therapeutic effect on bronchial asthma . It is acceptable for the adjuvant treatment of Cushing's syndrome, acromegaly. In addition,as an appetite enhancer,it is used for neuropathic fear of food. There are reports about acanthosis nigricans treatment, prevention of necrotizing pyoderma.
【Dosage 】oral often release dosage : (1) allergic diseases: adult, once 2~4mg, one day 2 or 3 times. (2) Cushing's syndrome, applicable to the treatment of cases of bilateral adrenal hyperplasia,it can inhibit the hypothalamic release of corticotropin releasing hormone (CRH) and inhibit the secretion of pituitary adrenocorticotropic hormone (ACTH), thereby lowering plasma ACTH and cortisol levels; adults start one day 8mg,which can be gradually increased to one day24mg; the usual dose is one day 12~24mg, divided doses,it needs long-term use; in the case of cortical function inadequate after total resection or subtotal bilateral adrenal, on one hand ,supple corticosteroids, on the other hand,take cyproheptadine,which can reduce the chance of occurrence of pituitary tumors.

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Uses: Anticoagulant, anti-allergic drugs. It can be used for urticaria, eczema, and allergic contact dermatitis, skin itching and other allergic reactions. It can also be used for Cushing's diseases and acromegaly.

Chemical Properties: White or slightly yellow, crystalline powder.

Uses: H1-antihistamine, antipruritic

Uses: Cyproheptadine is a first-generation antihistamine with additional anticholinergic, antiserotonergic, and local anesthetic properties. Cyproheptadine is a 5-HT2/5-HT1C serotonin receptor antagonist; H 1 histamine receptor antagonist; antipruritic.

Uses: Structural studies of an antihistimine

Uses

Cyproheptadine hydrochloride sesquihydrate has been used in:

testing anti-inflammatory activity in serotonin receptor (5-HT) induced inflammation
the inhibition of 5-HT in in vivo and in vitro bioassays in crabs
the inhibition of 5-HT in embryo physiological experiments

inhibition of calcitonin gene related peptide (CGRP)

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Definition: ChEBI: The sesquihydrate of cyproheptadine hydrochloride. Note that the drug named cyproheptadine hydrochloride generally refers to cyproheptadine hydrochloride sesquihydrate. A sedating antihistamine with antimuscarinic and calcium-channel blocking actions, it i used for the relief of allergic conditions including rhinitis, conjunctivitis due to inhalant allergens and foods, 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.

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Brand name: Periactin (Merck).

General Description: Cyproheptadine hydrochloride sesquihydrate is an antihistamine and is an antagonist of serotonin and histamine. It induced preventive effect against the development of pergolide-induced valvulopathy in a rat model.

Biochem/physiol Actions: Cyproheptadine hydrochloride sesquihydrate is a serotonin receptor (5-HT2/5-HT1C) antagonist, H1 histamine receptor antagonist and an antipruritic. The inhibition of 5-HT by cyproheptadine improves cognitive function in schizophrenia disorder. Cyproheptadine is effective for treating functional gastrointestinal disorders (FGIDs). Food and Drug Administration (FDA) approved cyproheptadine, has antidepressant and antiplatelet functionality. It may be effective in treating thromboembolic disorders. Cyproheptadine inhibits lysine methyltransferase 7/9 (Set7/9) leading to a decrease in estrogen receptor (ERα) expression and growth arrest in breast cancer cells.

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Veterinary Drugs and Treatments: Cyproheptadine may be useful in cats as an appetite stimulant. It potentially may be of benefit in the treatment of feline asthma or pruritus in cats, but clinical experience is marginal for this indication.
Cyproheptadine is an antihistamine but its efficacy is questionable for this indication in dogs. The drug may be useful as adjunctive therapy for Cushing’s syndrome probably as result of its antiserotonin activity, however one study demonstrated efficacy in less than 10% of dogs treated for pituitary dependent hyperadrenocorticism.
Cyproheptadine may be useful as adjunctive treatment in dogs or cats with serotonin syndrome.
In horses, cyproheptadine has been used for treating photic head shaking and pars intermedia dysfunction (Equine Cushing’s Disease).

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10. Related Questions

: What are the Similar Components of Cyproheptadine Hydrochloride and Their Applications in the Pharmaceutical Field? Cyproheptadine hydrochloride is a commonly used pharmaceutical ingredient with multiple effects. Besides Cyproheptadine hydrochloride, what are the other components that have similar effects? What ro..; What is cyproheptadine hydrochloride?Cyproheptadine (Periactin) is an antihistamine, similar in function to Benadryl, and so is used for runny nose, hives and other itchy reactions. I think it is less soporific (inducing drowsiness) than..

11. Realated Product Infomation