Quetiapine free base | CAS#111974-69-7 | 111974-72-2 | atypical antipsychotic

Quetiapine
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 319523

CAS#: 111974-69-7 (free base)

Description: Quetiapine, marketed as Seroquel, is an atypical antipsychotic approved for the treatment of schizophrenia, bipolar disorder, and along with an antidepressant to treat major depressive disorder. It is also sometimes used as a sleep aid because of its sedating effect but this use is not recommended. Quetiapine is a dopamine, serotonin, and adrenergic antagonist, and a potent antihistamine with clinically negligible anticholinergic properties. Quetiapine binds strongly to serotonin receptors; the drug acts as partial agonist at 5-HT1A receptors.

Chemical Structure

Quetiapine

CAS# 111974-69-7 (free base)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 319523
Name: Quetiapine
CAS#: 111974-69-7 (free base)
Chemical Formula: C21H25N3O2S
Exact Mass: 383.17
Molecular Weight: 383.510
Elemental Analysis: C, 65.77; H, 6.57; N, 10.96; O, 8.34; S, 8.36

Price and Availability

Size	Price	Availability
100mg	USD 350	2 Weeks
200mg	USD 550	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: ICI 204,636; ICI 204636; ICI-204636; ICI204636; quetiapine fumarate; Quetiapine; brand name: Seroquel.

IUPAC/Chemical Name: 2-(2-(4-dibenzo[b,f][1,4]thiazepine- 11-yl- 1-piperazinyl)ethoxy)ethanol

InChi Key: URKOMYMAXPYINW-UHFFFAOYSA-N

InChi Code: InChI=1S/C21H25N3O2S/c25-14-16-26-15-13-23-9-11-24(12-10-23)21-17-5-1-3-7-19(17)27-20-8-4-2-6-18(20)22-21/h1-8,25H,9-16H2

SMILES Code: OCCOCCN1CCN(C2=NC3=CC=CC=C3SC4=CC=CC=C24)CC1

Appearance: TBD

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, ethanol, and water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info: Related CAS# CAS# 111974-72-2 ( Quetiapine hemifumarate) CAS#111974-69-7 ( Quetiapine free base).

Product Data:

Product Data

Instruction:

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Biological target:	Quetiapine is a dopamine, serotonin, and adrenergic antagonist, and a potent antihistamine with clinically negligible anticholinergic properties. Quetiapine has moderate to high affinity for the human D2, HT1A, 5-HT2A, 5-HT2C receptor with pKis of 7.25, 5.74, 7.54, 5.55. It has antidepressant and anxiolytic effects.
In vitro activity:	Using PC12 cell cultures and the MTT assay for cell viability found that the atypical antipsychotics clozapine, quetiapine, and risperidone may exert a neuroprotective function after serum withdrawal through the modulation of SOD1 and p75NTR expression. They also found that 1) the atypical antipsychotics (clozapine, quetiapine, and risperidone) can protect PC12 cells from death after serum withdrawal and 2) these drugs up-regulated the SOD1 gene expression to more than 120% and also down-regulated p75NTR mRNA levels to less than 65% of their respective control values Reference: J Neurosci Res. 2002 Jul 15;69(2):278-83. https://pubmed.ncbi.nlm.nih.gov/12111809/
In vivo activity:	Quetiapine significantly reduced depressive-like behaviors induced by chronic mild stress in adult rats. MPO activity and IL-6 levels increased in the serum of animals submitted to CMS. Quetiapine significantly reduced MPO activity and IL-6 levels. These results corroborate other evidence, indicating that chronic stress is a relevant phenomenon in the etiology of depression and suggesting that quetiapine induces an antidepressant effect because it reduces oxidative and inflammatory mechanisms. Reference: Naunyn Schmiedebergs Arch Pharmacol. 2023 Feb 3. https://pubmed.ncbi.nlm.nih.gov/36735044/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	100.0	260.75
	Ethanol	100.0	260.75
	Water	0.1	0.26

Preparing Stock Solutions

The following data is based on the product molecular weight 383.51 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:	1. Le Daré B, Ferron PJ, Allard PM, Clément B, Morel I, Gicquel T. New insights into quetiapine metabolism using molecular networking. Sci Rep. 2020 Nov 16;10(1):19921. doi: 10.1038/s41598-020-77106-x. PMID: 33199804; PMCID: PMC7669884. 2. Bai O, Wei Z, Lu W, Bowen R, Keegan D, Li XM. Protective effects of atypical antipsychotic drugs on PC12 cells after serum withdrawal. J Neurosci Res. 2002 Jul 15;69(2):278-83. doi: 10.1002/jnr.10290. PMID: 12111809. 3. Grolli RE, Bertollo AG, Behenck JP, de Araujo Borba L, Plissari ME, Soares SJB, Manica A, da Silva Joaquim L, Petronilho F, Quevedo J, Bagatini MD, Réus GZ, Ignácio ZM. Quetiapine effect on depressive-like behaviors, oxidative balance, and inflammation in serum of rats submitted to chronic stress. Naunyn Schmiedebergs Arch Pharmacol. 2023 Feb 3. doi: 10.1007/s00210-023-02406-8. Epub ahead of print. PMID: 36735044. 4. Agrawal MB, Patel MM. Optimization and in vivo evaluation of quetiapine-loaded transdermal drug delivery system for the treatment of schizophrenia. Drug Dev Ind Pharm. 2020 Nov;46(11):1819-1831. doi: 10.1080/03639045.2020.1821051. Epub 2020 Sep 17. PMID: 32896163.
In vitro protocol:	1. Le Daré B, Ferron PJ, Allard PM, Clément B, Morel I, Gicquel T. New insights into quetiapine metabolism using molecular networking. Sci Rep. 2020 Nov 16;10(1):19921. doi: 10.1038/s41598-020-77106-x. PMID: 33199804; PMCID: PMC7669884. 2. Bai O, Wei Z, Lu W, Bowen R, Keegan D, Li XM. Protective effects of atypical antipsychotic drugs on PC12 cells after serum withdrawal. J Neurosci Res. 2002 Jul 15;69(2):278-83. doi: 10.1002/jnr.10290. PMID: 12111809.
In vivo protocol:	1. Grolli RE, Bertollo AG, Behenck JP, de Araujo Borba L, Plissari ME, Soares SJB, Manica A, da Silva Joaquim L, Petronilho F, Quevedo J, Bagatini MD, Réus GZ, Ignácio ZM. Quetiapine effect on depressive-like behaviors, oxidative balance, and inflammation in serum of rats submitted to chronic stress. Naunyn Schmiedebergs Arch Pharmacol. 2023 Feb 3. doi: 10.1007/s00210-023-02406-8. Epub ahead of print. PMID: 36735044. 2. Agrawal MB, Patel MM. Optimization and in vivo evaluation of quetiapine-loaded transdermal drug delivery system for the treatment of schizophrenia. Drug Dev Ind Pharm. 2020 Nov;46(11):1819-1831. doi: 10.1080/03639045.2020.1821051. Epub 2020 Sep 17. PMID: 32896163.

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1: Hutton P, Taylor PJ, Mulligan L, Tully S, Moncrieff J. Quetiapine immediate release v. placebo for schizophrenia: systematic review, meta-analysis and reappraisal. Br J Psychiatry. 2015 May;206(5):360-70. doi: 10.1192/bjp.bp.114.154377. Review. PubMed PMID: 25934300.

2: Piróg-Balcerzak A, Habrat B, Mierzejewski P. [Misuse and abuse of quetiapine]. Psychiatr Pol. 2015 Jan-Feb;49(1):81-93. doi: 10.12740/PP/32923. Review. Polish. PubMed PMID: 25844412.

3: Styczeń K, Datka W, Jaeschke R, Drozdowicz K, Siwek M, Dudek D. [The place of quetiapine extended release in the treatment of mental disorders]. Psychiatr Pol. 2015 Jan-Feb;49(1):67-80. doi: 10.12740/PP/33909. Review. Polish. PubMed PMID: 25844411.

4: Pringsheim T, Gardner D, Patten SB. Adjunctive treatment with quetiapine for major depressive disorder: are the benefits of treatment worth the risks? BMJ. 2015 Mar 4;350:h569. doi: 10.1136/bmj.h569. Review. PubMed PMID: 25739588.

5: Kreys TJ, Phan SV. A literature review of quetiapine for generalized anxiety disorder. Pharmacotherapy. 2015 Feb;35(2):175-88. doi: 10.1002/phar.1529. Review. PubMed PMID: 25689246.

6: Masi G, Milone A, Veltri S, Iuliano R, Pfanner C, Pisano S. Use of quetiapine in children and adolescents. Paediatr Drugs. 2015 Apr;17(2):125-40. doi: 10.1007/s40272-015-0119-3. Review. PubMed PMID: 25686575.

7: Millard HY, Wilson BA, Noordsy DL. Low-dose quetiapine induced or worsened mania in the context of possible undertreatment. J Am Board Fam Med. 2015 Jan-Feb;28(1):154-8. doi: 10.3122/jabfm.2015.01.140105. Review. PubMed PMID: 25567837.

8: Samalin L, Tremey A, Llorca PM. Quetiapine extended release for the treatment of bipolar disorder. Expert Rev Neurother. 2014 Sep;14(9):987-1005. doi: 10.1586/14737175.2014.946407. Epub 2014 Aug 6. Review. PubMed PMID: 25096854.

9: Hasnain M, Vieweg WV, Howland RH, Kogut C, Breden Crouse EL, Koneru JN, Hancox JC, Digby GC, Baranchuk A, Deshmukh A, Pandurangi AK. Quetiapine, QTc interval prolongation, and torsade de pointes: a review of case reports. Ther Adv Psychopharmacol. 2014 Jun;4(3):130-8. doi: 10.1177/2045125313510194. Review. PubMed PMID: 25057346; PubMed Central PMCID: PMC4107702.

10: Howland RH. The comparative cardiac effects of haloperidol and quetiapine: parsing a review. J Psychosoc Nurs Ment Health Serv. 2014 Jun;52(6):23-6. doi: 10.3928/02793695-20140515-01. Review. PubMed PMID: 24967672.

11: Liou LS, Hung YJ, Hsieh CH, Hsiao FC. Aggravation of hypertriglyceridemia and acute pancreatitis in a bipolar patient treated with quetiapine. Yonsei Med J. 2014 May;55(3):831-3. doi: 10.3349/ymj.2014.55.3.831. Epub 2014 Apr 1. Review. PubMed PMID: 24719155; PubMed Central PMCID: PMC3990081.

12: Anderson SL, Vande Griend JP. Quetiapine for insomnia: A review of the literature. Am J Health Syst Pharm. 2014 Mar 1;71(5):394-402. doi: 10.2146/ajhp130221. Review. PubMed PMID: 24534594.

13: Vella T, Mifsud J. Interactions between valproic acid and quetiapine/olanzapine in the treatment of bipolar disorder and the role of therapeutic drug monitoring. J Pharm Pharmacol. 2014 Jun;66(6):747-59. doi: 10.1111/jphp.12209. Epub 2014 Jan 7. Review. PubMed PMID: 24392714.

14: Asmal L, Flegar SJ, Wang J, Rummel-Kluge C, Komossa K, Leucht S. Quetiapine versus other atypical antipsychotics for schizophrenia. Cochrane Database Syst Rev. 2013 Nov 18;11:CD006625. doi: 10.1002/14651858.CD006625.pub3. Review. PubMed PMID: 24249315.

15: Weisler R, McIntyre RS, Bauer M. Extended-release quetiapine fumarate in the treatment of patients with major depressive disorder: adjunct therapy. Expert Rev Neurother. 2013 Nov;13(11):1183-200. doi: 10.1586/14737175.2013.846519. Review. PubMed PMID: 24175721.

16: Weisler R, McIntyre RS. The role of extended-release quetiapine fumarate monotherapy in the treatment of patients with major depressive disorder. Expert Rev Neurother. 2013 Nov;13(11):1161-82. doi: 10.1586/14737175.2013.846520. Review. PubMed PMID: 24175720.

17: López-Muñoz F, Alamo C. Active metabolites as antidepressant drugs: the role of norquetiapine in the mechanism of action of quetiapine in the treatment of mood disorders. Front Psychiatry. 2013 Sep 12;4:102. doi: 10.3389/fpsyt.2013.00102. Review. PubMed PMID: 24062697; PubMed Central PMCID: PMC3770982.

18: Zhornitsky S, Wee Yong V, Koch MW, Mackie A, Potvin S, Patten SB, Metz LM. Quetiapine fumarate for the treatment of multiple sclerosis: focus on myelin repair. CNS Neurosci Ther. 2013 Oct;19(10):737-44. doi: 10.1111/cns.12154. Epub 2013 Jul 22. Review. PubMed PMID: 23870612.

19: Carney AC. Efficacy of quetiapine off-label uses: data synthesis. J Psychosoc Nurs Ment Health Serv. 2013 Aug;51(8):11-8. doi: 10.3928/02793695-20130709-01. Epub 2013 Jul 18. Review. PubMed PMID: 23848159.

20: Suttajit S, Srisurapanont M, Xia J, Suttajit S, Maneeton B, Maneeton N. Quetiapine versus typical antipsychotic medications for schizophrenia. Cochrane Database Syst Rev. 2013 May 31;5:CD007815. doi: 10.1002/14651858.CD007815.pub2. Review. PubMed PMID: 23728667.

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