111974-74-4 Usage
Description
11-(1-Piperazinyl)-dibenzo[b,f][1,4]thiazepine dihydrochloride, also known as Norquetiapine 2HCl (111974-74-4), is a pharmacologically active metabolite of quetiapine (Seroquel). It exhibits distinct pharmacological activity from quetiapine and is characterized by its pale-yellow solid appearance. 11-(1-Piperazinyl)-dibenzo[b,f][1,4]thiazepine dihydrochloride plays a significant role in the antidepressant activity of quetiapine and is known to activate ERK1/2 and induce the release of BDNF in C6 glioma cells. Additionally, it inhibits the norepinephrine transporter, which may contribute to the antipsychotic activity of quetiapine.
Uses
Used in Pharmaceutical Industry:
11-(1-Piperazinyl)-dibenzo[b,f][1,4]thiazepine dihydrochloride is used as an active metabolite for its distinct pharmacological properties. It contributes to the antidepressant activity of quetiapine by activating ERK1/2 and inducing the release of BDNF in C6 glioma cells. Furthermore, it is used as an antipsychotic agent due to its inhibition of the norepinephrine transporter.
Used in Research and Development:
In the field of research and development, 11-(1-Piperazinyl)-dibenzo[b,f][1,4]thiazepine dihydrochloride serves as a valuable compound for studying the mechanisms of action and potential applications of quetiapine. Its distinct pharmacological activity and role in the antidepressant and antipsychotic effects of quetiapine make it an important subject for further investigation and potential development of new therapeutic agents.
Used in Quality Control and Impurity Profiling:
11-(1-Piperazinyl)-dibenzo[b,f][1,4]thiazepine dihydrochloride, as a metabolite of quetiapine, is also used in the quality control and impurity profiling of quetiapine pharmaceutical products. It helps ensure the safety, efficacy, and purity of the drug by monitoring the presence and concentration of this specific metabolite in the final product.
References
1) Altamura?et al.?(2012),?Effect of quetiapine and norquetiapine on anxiety and depression in major psychoses using a pharmacokinetic approach: a prospective observational study; Clin. Drug Investig.,?32?213
2) Lopez Munoz and Alamo (2013),?Active metabolites as antidepressant drugs: the role of norquetiapine in the mechanism of action of quetiapine in the treatment of mood disorders; Front. Psychiatry,?4?102
3) Di. Benedetto?et al.?(2012),?N-desalkylquetiapine activates ERK1/2 to induce GDNF release in C6 glioma cells: a putative cellular mechanism for quetiapine as antidepressant; Neuropharmacology,?62?209
4) Bjorkholm?et al.?(2013),?Role of concomitant inhibition of the norepinephrine transporter for the antipsychotic effect of quetiapine; Eur. Neuropsychopharmacol.,?23?709
Check Digit Verification of cas no
The CAS Registry Mumber 111974-74-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,1,9,7 and 4 respectively; the second part has 2 digits, 7 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 111974-74:
(8*1)+(7*1)+(6*1)+(5*9)+(4*7)+(3*4)+(2*7)+(1*4)=124
124 % 10 = 4
So 111974-74-4 is a valid CAS Registry Number.
InChI:InChI=1/C17H17N3S.2ClH/c1-3-7-15-13(5-1)17(20-11-9-18-10-12-20)19-14-6-2-4-8-16(14)21-15;;/h1-8,18H,9-12H2;2*1H
111974-74-4Relevant articles and documents
Design, synthesis and anticancer activity of N-(1-(4-(dibenzo[b,f][1,4]thiazepin-11-yl)piperazin-1-yl)-1-oxo-3-phenylpropan-2-yl derivatives
Gudisela, Mura Reddy,Srinivasu,Mulakayala, Chaitanya,Bommu, Praveen,Rao, M.V. Basaveswara,Mulakayala, Naveen
, p. 4140 - 4145 (2017)
Novel N-(1-(4-(dibenzo[b,f][1,4]thiazepin-11-yl)piperazin-1-yl)-1-oxo-3-phenylpropan-2-yl derivatives were designed, synthesized and their chemical structures were confirmed by 1H NMR, 13C NMR and Mass spectra. The anticancer activities of the newly synthesized compounds were evaluated in vitro against three human cancer cell lines including K562, Colo-205 and MDA-MB 231 by MTT assay. The screening results showed that five compounds (16b, 16d, 16i, 16p and 16q) exhibited potent cytotoxic activities with IC50 values between 20 and 40 μM. Further in vitro studies revealed that inhibition of sirtuins could be the possible mechanism of action of these molecules.
PROCESS FOR THE PREPARATION OF QUETIAPINE FUMARATE
-
Page/Page column 23-24, (2010/09/18)
The present invention relates to an improved process for the preparation of quetiapine and pharmaceutically acceptable salts. It also relates to improved process for the preparation of intermediates of quetiapine.
An Improved and single pot process for the production of quetiapine hemifumarate substantially free from potential impurities
Niphade, Navnath C.,Mali, Anil C.,Pandit, Bhushan S.,Jagtap, Kunal M.,Jadhav, Sanjay A.,Jachak, Madhukar N.,Mathad, Vijayavitthal T.
scheme or table, p. 792 - 797 (2010/04/22)
An improved and single pot process for the preparation of Quetiapine hemifumarate (1), an antipsychotic drug, free from potential impurities is reported with an overall yield of 80%. The reported process for its preparation suffers from the drawback of producing potential impurities identified as 11-piperazin-1- yldibenzo[b,f][1,4]thiazepine (6), 2-(4-dibenzo[b,f][1,4] thiazepin-11- ylpiperazin-1-yl)ethanol (10), dimer (9), and N-methyl- Nphenyldibenzo[ b,f][1,4]thiazapine-11-amine (14). Elimination of these impurities in the process is achieved by chlorination of 3 followed by in situ condensation of obtained 4 with highly pure 8 and subsequently establishing the pH based workup to obtain free base 2, which is further converted to quetiapine hemifumarate salt free from all these impurities. In this report, different aspects of process development such as scheme selection, optimization of different process parameters, identification, synthesis, origin and control of impurities, and development of an accurate analytical method during the development of a scalable process for quetiapine hemifumarate are discussed.