Cyproheptadine

Base Information

• Chemical Name: Cyproheptadine
• CAS No.: 129-03-3
• Molecular Formula: C21H21 N
• Molecular Weight: 287.404
• Hs Code.: 29143900
• European Community (EC) Number: 204-928-9,623-762-1
• UNII: 2YHB6175DO
• DSSTox Substance ID: DTXSID8022872
• Nikkaji Number: J5.419D
• Wikipedia: Cyproheptadine
• Wikidata: Q417884
• NCI Thesaurus Code: C61695
• RXCUI: 3013
• Pharos Ligand ID: W5YGQF7BFF6K
• Metabolomics Workbench ID: 42791
• ChEMBL ID: CHEMBL516
• Mol file: 129-03-3.mol

Synonyms:Antergan;Cyproheptadine;Dihexazin;Periactin;Peritol;Viternum

Chemical Property of Cyproheptadine

Chemical Property:

• Appearance/Colour: Colorless liquid, sweet, almond odor.
• Vapor Pressure: 6.03E-08mmHg at 25°C
• Melting Point: 112.3-113.3°
• Refractive Index: 1.8240 (estimate)
• Boiling Point: 440.1°Cat760mmHg
• PKA: pKa 8.87 (Uncertain)
• Flash Point: 194.5°C
• PSA: 3.24000
• Density: 1.115g/cm³
• LogP: 5.43780
• Water Solubility.: 317.6ug/L(22.5 oC)
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 287.167399674
• Heavy Atom Count: 22
• Complexity: 423

Purity/Quality:

98%,99%, ^*data from raw suppliers

Cycloheptadine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antihistamines
• Canonical SMILES: CN1CCC(=C2C3=CC=CC=C3C=CC4=CC=CC=C42)CC1
• Recent ClinicalTrials: Noninvasive Markers of Functional Nausea in Children
• Description: Cyproheptadine has antianaphylactic activity that is associated with its ability to slow down the release of histamine and other mediators from fat cells.
• Uses: Antihistaminic; antipruritic. 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.
• Therapeutic Function: Antipruritic, Antihistaminic, Appetite stimulant

Technology Process of Cyproheptadine

There total 6 articles about Cyproheptadine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

5-(1-methyl-4-piperidyl)-5H-dibenzocyclohepten-5-ol (3967-32-6) → cyproheptadine (129-03-3)

Guidance literature:

With formic acid; at 100 ℃; for 2h;

DOI:10.1021/jo100563p

Reference yield:

dibenzosuberenon (2222-33-5) → cyproheptadine (129-03-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / tetrahydrofuran / 70 °C

2: 83 percent / HOAc, conc. HCl / 2 h / 120 °C

With hydrogenchloride; acetic acid; In tetrahydrofuran;

DOI:10.1002/ardp.19963290206

Reference yield:

ethyl 4-(5H-dibenzocyclohepten-5-ylidene)-1-piperidinecarboxylate (121138-82-7) → cyproheptadine (129-03-3)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 2h; Yield given; Heating;

DOI:10.1016/S0040-4020(01)89809-4

upstream raw materials:

5-(1-methyl-4-piperidyl)-5H-dibenzocyclohepten-5-ol

ethyl 4-(5H-dibenzocyclohepten-5-ylidene)-1-piperidinecarboxylate

(1-methyl-4-piperidyl)magnesium chloride

dibenzosuberenon

Downstream raw materials:

4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine

Cyproheptadine 10,11-epoxide

(4,4'-dimethyl-1,1'-biphenyl)

Refernces

• 1、 Hatano, Manabu,Ito, Orie,Suzuki, Shinji,Ishihara, Kazuaki. "Zinc(II)-catalyzed addition of grignard reagents to ketones". supporting information; experimental part. p. 5008 - 5016. Retrieved 2010/10/04.
• 2、 Loughhead, David G.. "UNUSUAL REDUCTIONS INDUCED BY FORMIC ACID". . p. 5701 - 5702. Retrieved 2007/10/02.