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
• Article Data: 8

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

N-Desmethyl Cyproheptadine is a metabolite of Cyproheptadine (C989200, HCl,H2O); a first-generation antihistamine with additional anticholinergic, antiserotonergic, and local anesthetic properties. Also a 5-HT2/5-HT1C serotonin receptor antagonist, H1 histamine receptor antagonist, and antipruritic.

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

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

Downstream Products

• 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 
• 184107-20-8 methyl (S)-2-benzyloxycarbonylamino-3-[4-(5H-dibenzo[a,d]-cyclohepten-5-ylidene)piperidin-1-yl]propionate 
• 184107-30-0 Ethyl α-{(S)-2-benzyloxycarbonylamino-3-[4-(5H-dibenzo[a,d]-cyclohepten-5-ylidene)piperidine-1-yl]propionylamino}acetate 
• 184107-25-3 (S)-2-benzyloxycarbonylamino-3-[4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidin-1-yl]propionic acid 

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.

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.

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.