14051-46-8

Basic information

• Product Name: desmethylcyproheptadine
• Synonyms: N-Desmethyl Cyproheptadine;4-Dibenzo[a,d]cyclohepten-5-ylidene-piperidine
• CAS NO: 14051-46-8
• Molecular Formula: C₂₀H₁₉N
• Molecular Weight: 273.377
• Mol File: 14051-46-8.mol

Chemical Properties

• Boiling Point: 432.6°C at 760 mmHg
• Flash Point: 230.6°C
• Appearance: /
• Density: 1.127g/cm³
• Vapor Pressure: 1.09E-07mmHg at 25°C
• Refractive Index: 1.633
• CAS DataBase Reference: desmethylcyproheptadine(CAS DataBase Reference)
• NIST Chemistry Reference: desmethylcyproheptadine(14051-46-8)
• EPA Substance Registry System: desmethylcyproheptadine(14051-46-8)

Safety Data

• Hazardous Substances Data: 14051-46-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Desmethylcyproheptadine is used as an active pharmaceutical ingredient for its various properties, including its antihistamine, anticholinergic, antiserotonergic, and local anesthetic effects. It is particularly useful in treating allergic reactions, as it can counteract the histamine release that causes symptoms like itching and inflammation.
Used in Antidepressant Applications:
Desmethylcyproheptadine is used as an adjunct in the treatment of depression, particularly when serotonin and histamine receptors are involved in the condition. Its antagonistic action on these receptors can help alleviate depressive symptoms.
Used in Antipruritic Applications:
Desmethylcyproheptadine is used as an antipruritic agent to relieve itching caused by various skin conditions, such as eczema, dermatitis, and urticaria. Its histamine receptor antagonist property helps reduce the itchiness associated with these conditions.
Used in Neurological Applications:
Desmethylcyproheptadine is used in the treatment of certain neurological disorders, where its antiserotonergic and anticholinergic properties can help manage symptoms like migraines, headaches, and neuropathic pain.
Used in Anesthetic Applications:
Due to its local anesthetic properties, desmethylcyproheptadine can be used in medical procedures to provide local pain relief and numbness in specific areas of the body.

InChI:InChI=1/C20H19N/c1-3-7-18-15(5-1)9-10-16-6-2-4-8-19(16)20(18)17-11-13-21-14-12-17/h1-10,21H,11-14H2

Upstream product

• 121138-82-7 ethyl 4-(5H-dibenzocyclohepten-5-ylidene)-1-piperidinecarboxylate 
• 63463-36-5 (1-methyl-4-piperidyl)magnesium chloride 
• 71-36-3 butan-1-ol 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 2222-33-5 dibenzosuberenon 
• 969-33-5 cyproheptadine hydrochloride 
• 3967-32-6 5-(1-methyl-4-piperidyl)-5H-dibenzocyclohepten-5-ol 
• 129-03-3 cyproheptadine 

Downstream Products

• 184107-20-8 methyl (S)-2-benzyloxycarbonylamino-3-[4-(5H-dibenzo[a,d]-cyclohepten-5-ylidene)piperidin-1-yl]propionate 
• 184107-25-3 (S)-2-benzyloxycarbonylamino-3-[4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidin-1-yl]propionic acid 
• 184107-30-0 Ethyl α-{(S)-2-benzyloxycarbonylamino-3-[4-(5H-dibenzo[a,d]-cyclohepten-5-ylidene)piperidine-1-yl]propionylamino}acetate 
• 500895-09-0 cyclohexyl 2-[4-(5H-dibenzo[a,d][7]annulen-5-ylidene)-1-piperidinyl]-2-oxoethylcarbamate 
• 153509-99-0 C₂₇H₂₅N 
• 153510-93-1 C₂₈H₂₇NO 

Relevant articles and documents

Amphoteric drugs. II. Synthesis and antiallergic activity of C4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene) piperidino]alkanoic acid derivatives and related compounds

A simple method of transforming classical tricyclic antihistaminics into nonsedative antiallergic agents with equal potency in rats and guinea-pigs is described. A series of C4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-piperidino] alkanoic acid derivatives (6a) and related compounds (6b-f) were synthesized and examined for antiallergic and antihistaminic activities and effects on the central nervous system (CNS) in comparison with the corresponding N-methyl derivatives (2a-f). N-Alkylcarboxylic acids (6a-f) showed stronger inhibitory effects on 48 h homologous passive cutaneous anaphylaxis (PCA) in rats than 2a-f, and also were less effective in prolongation of the sleeping time on hexobarbital-induced anesthesia in mice in comparison with 2a-f. As a result of further modification, it was found that introduction of an oxygen atom into the central ring of the tricyclic system in amphoteric compounds enhanced their antiallergic and antihistaminic activities. 3-[4-(6H-Dibenz[b,e]oxepin-11-ylidene)piperidino]propionic acid (6c) exhibited strong inhibitory effects on 48 h homologous PCA in rats (ED50 = 0.067 mg/kg, p.o.) and on histamine-induced bronchoconstriction in anesthetized guinea-pigs (ED50 = 0.0085 mg/kg, p.o.), and thus is a promising candidate as an antiallergic agent.

Cyproheptadine derivatives, process for preparing the same and composition for promoting appetite comprising the same

The present invention provides a cyprotadine derivative or a pharmaceutically acceptable salt thereof, a preparation method thereof, and a composition for promoting appetite in a mammal comprising the same. In mHyHyHypoE cell lines, the cyprohepcidin deri

Reversed isoniazids: Design, synthesis and evaluation against Mycobacterium tuberculosis

Novel reversed isoniazid (RINH) agents were synthesized by covalently linking isoniazid with various efflux pump inhibitor (EPI) cores and their structural motifs. These RINH agents were then evaluated for anti-mycobacterial activity against sensitive, isoniazid mono-resistant and MDR clinical isolates of M. tuberculosis and a selected number of compounds were also tested ex vivo for intracellular activity as well as in the ethidium bromide (EB) assay for efflux pump inhibition efficacy. The potency of some compounds against various strains of M. tuberculosis (4a–c, 7 and 8; H37Rv-MIC99 ≤1.25 μM, R5401-MIC99 ≤2.5 μM, X_61-MIC99 ≤5 μM) demonstrated the potential of the reversed anti-TB agent strategy towards the development of novel anti-mycobacterial agents to address the rapidly growing issue of resistance. Further, macrophage activity with >90% inhibition by 1a–c and 3b (MIC90 ≤13.42 μM) and inhibition of EB efflux demonstrated by these compounds are encouraging.

Loratadine analogues as MAGL inhibitors Dedicated to Dr. Sameer Agarwal, principal scientist at Zydus Research Centre (ZRC, India)

Compound 12a (JZP-361) acted as a potent and reversible inhibitor of human recombinant MAGL (hMAGL, IC50 = 46 nM), and was found to have almost 150-fold higher selectivity over human recombinant fatty acid amide hydrolase (hFAAH, IC50 = 7.24 μM) and 35-fold higher selectivity over human α/β-hydrolase-6 (hABHD6, IC50 = 1.79 μM). Additionally, compound 12a retained H1 antagonistic affinity (pA2 = 6.81) but did not show cannabinoid receptor activity, when tested at concentrations ≤10 μM. Hence, compound 12a represents a novel dual-acting pharmacological tool possessing both MAGL-inhibitory and antihistaminergic activities.

HETEROCYCLIC COMPOUND AND H1 RECEPTOR ANTAGONIST

A heterocyclic compound useful as an antiallergic agent is provided. A compound represented by the following formula (1) or a salt thereof: wherein the ring A is a homocyclic or heterocyclic ring; the ring B is a heterocyclic ring which contains G and nitrogen atom N as constituent atoms thereof, wherein G is CH or N; R1 is a carbonyl group or an alkylene group; R2a and R2b are an alkyl group, a cycloalkyl group, an aryl group, or a heterocyclic group; X is an oxygen atom or a sulfur atom; Z is a hydroxyl group, an alkoxy group, a cycloalkyloxy group, an aryloxy group, an aralkyloxy group, an amino group, or an N-substituted amino group; and n is 0 or 1; with the proviso that when the ring A is a benzene ring or when the ring B is a piperazine ring, R1 is an alkylene group which may have a substituent.

Synthesis and pharmacology of combined histamine H1-/H2-receptor antagonists containing diphenhydramine and cyproheptadine derivatives

The classical histamine H1-receptor antagonists diphenhydramine (3a) and cyproheptadine (9) and their derivatives (3b-d, 10) were connected with a 2-guanidinothiazole containing structure (28) derived from the H2-receptor antagonist tiotidine in order to obtain combined H1/H2-receptor antagonists. The two moieties were not directly linked together, but were separated by a polymethylene spacer and a polar group (nitroethenediamine or urea). Thus 12 compounds were obtained that proved in vitro to possess high H1- and H2-receptor antagonist activity at the isolated guinea-pig ileum (H1) and the isolated guinea-pig right atrium (H2), respectively. The incorporation of the diphenhydramine as well as the cyproheptadine component provides high affinity to H1-receptors. The tricyclic cyproheptadine and its 10,11-dihydro derivative (30-32, 34), however, cause a decrease of H2-receptor antagonist potency compared to the diphenhydramines (29a-d, 33a-d). Using nitroethenediamine as the polar group is apparently more favourable to H1- and H2-receptor affinity as the urea function. All compounds elicit a dual mode of competitive and noncompetitive antagonism. Among the novel compounds the nitroethenediamines with 4-fluoro- or 4-methyl-substituted diphenhydramine as H1-receptor antagonist moiety (29c, d) display the most potent H1- and H2-receptor antagonist effects. The presented concept is a very promising way to combine H1- and H2-receptor antagonist properties in one molecule.

Piperidine derivatives and pharmaceutical compositions comprising the same

A piperidine derivative represented by the following general formula (I): STR1 wherein R represents a hydrogen atom or a lower alkyl group; X represents --CH=CH--, --CH2 CH2 --, or --CH2 O--; Y represents an alkylene group having 1 to 5 carbon atoms which may be optionally substituted with a lower alkyl group, or Y represents an --A--O--B-- group wherein A and B are the same or different and each independently represented an alkylene group having 1 to 3 carbon atoms which may be optionally substituted with a lower alkyl group is disclosed. Also disclosed are a pharmacologically acceptable salt of a compound of formula (I), a method for preparation of a compound of formula (I), an antihistaminic and antiallergic agent comprising a compound of formula (I), a pharmaceutical composition comprising a compound of formula (I), and a method for the treatment of an allergic disease by administering a compound of formula (I).