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MedKoo Cat#: 591312 | Name: Phenothiazine
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Description:

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

Phenothiazine is a synthetic compound that is used in veterinary medicine to treat parasitic infestations of animals.

Chemical Structure

Phenothiazine
Phenothiazine
CAS#92-84-2

Theoretical Analysis

MedKoo Cat#: 591312

Name: Phenothiazine

CAS#: 92-84-2

Chemical Formula: C12H9NS

Exact Mass: 199.0456

Molecular Weight: 199.27

Elemental Analysis: C, 72.33; H, 4.55; N, 7.03; S, 16.09

Price and Availability

Size Price Availability Quantity
25g USD 200.00
500g USD 340.00
1kg USD 530.00
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Related CAS #
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Synonym
Phenothiazine; NSC 2037; NSC-2037 NSC2037
IUPAC/Chemical Name
10H-Phenothiazine
InChi Key
WJFKNYWRSNBZNX-UHFFFAOYSA-N
InChi Code
InChI=1S/C12H9NS/c1-3-7-11-9(5-1)13-10-6-2-4-8-12(10)14-11/h1-8,13H
SMILES Code
C12=CC=CC=C1NC3=C(C=CC=C3)S2
Appearance
Solid powder
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
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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Phenothiazine is an antibiotic which has insecticidal, fungicidal, antibacterial and anthelmintic activities.
In vitro activity:
The present study found that phenothiazine antipsychotics increased calcium mobilization and activated mast cells to release β-hexosaminidase, histamine, and tumor necrosis factor-α via Mas-related G-protein-coupled receptor member X2 (MRGPRX2) in vitro. Reference: Mol Immunol. 2019 Jul;111:118-127. https://pubmed.ncbi.nlm.nih.gov/31051313/
In vivo activity:
This study’s findings showed that PTZ (phenothiazine) rescues rotenone (ROT) toxicity in primary ventral midbrain neuronal cultures by preserving neuronal integrity and reducing protein thiol oxidation. Long-term treatment with PTZ improved animal weight, survival rate, and behavioral deficits in ROT-lesioned rats. PTZ protected DA content and fiber density in the striatum and DA neurons in the SN against the deleterious effects of ROT. Reference: Redox Biol. 2019 Jun;24:101164. https://pubmed.ncbi.nlm.nih.gov/30925294/
Solvent mg/mL mM comments
Solubility
DMSO 95.0 476.74
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 199.27 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.

Recalculate based on batch purity %
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. Hou Y, Che D, Wei D, Wang C, Xie Y, Zhang K, Cao J, Fu J, Zhou N, He H. Phenothiazine antipsychotics exhibit dual properties in pseudo-allergic reactions: Activating MRGPRX2 and inhibiting the H1 receptor. Mol Immunol. 2019 Jul;111:118-127. doi: 10.1016/j.molimm.2019.04.008. Epub 2019 Apr 30. PMID: 31051313. 2. Hempel C, Nörenberg W, Sobottka H, Urban N, Nicke A, Fischer W, Schaefer M. The phenothiazine-class antipsychotic drugs prochlorperazine and trifluoperazine are potent allosteric modulators of the human P2X7 receptor. Neuropharmacology. 2013 Dec;75:365-79. doi: 10.1016/j.neuropharm.2013.07.027. Epub 2013 Aug 14. PMID: 23954492. 3. Tapias V, McCoy JL, Greenamyre JT. Phenothiazine normalizes the NADH/NAD+ ratio, maintains mitochondrial integrity and protects the nigrostriatal dopamine system in a chronic rotenone model of Parkinson's disease. Redox Biol. 2019 Jun;24:101164. doi: 10.1016/j.redox.2019.101164. Epub 2019 Mar 21. PMID: 30925294; PMCID: PMC6440170. 4. Songarj P, Luh C, Staib-Lasarzik I, Engelhard K, Moosmann B, Thal SC. The antioxidative, non-psychoactive tricyclic phenothiazine reduces brain damage after experimental traumatic brain injury in mice. Neurosci Lett. 2015 Jan 1;584:253-8. doi: 10.1016/j.neulet.2014.10.037. Epub 2014 Oct 28. PMID: 25449871.
In vitro protocol:
1. Hou Y, Che D, Wei D, Wang C, Xie Y, Zhang K, Cao J, Fu J, Zhou N, He H. Phenothiazine antipsychotics exhibit dual properties in pseudo-allergic reactions: Activating MRGPRX2 and inhibiting the H1 receptor. Mol Immunol. 2019 Jul;111:118-127. doi: 10.1016/j.molimm.2019.04.008. Epub 2019 Apr 30. PMID: 31051313. 2. Hempel C, Nörenberg W, Sobottka H, Urban N, Nicke A, Fischer W, Schaefer M. The phenothiazine-class antipsychotic drugs prochlorperazine and trifluoperazine are potent allosteric modulators of the human P2X7 receptor. Neuropharmacology. 2013 Dec;75:365-79. doi: 10.1016/j.neuropharm.2013.07.027. Epub 2013 Aug 14. PMID: 23954492.
In vivo protocol:
1. Tapias V, McCoy JL, Greenamyre JT. Phenothiazine normalizes the NADH/NAD+ ratio, maintains mitochondrial integrity and protects the nigrostriatal dopamine system in a chronic rotenone model of Parkinson's disease. Redox Biol. 2019 Jun;24:101164. doi: 10.1016/j.redox.2019.101164. Epub 2019 Mar 21. PMID: 30925294; PMCID: PMC6440170. 2. Songarj P, Luh C, Staib-Lasarzik I, Engelhard K, Moosmann B, Thal SC. The antioxidative, non-psychoactive tricyclic phenothiazine reduces brain damage after experimental traumatic brain injury in mice. Neurosci Lett. 2015 Jan 1;584:253-8. doi: 10.1016/j.neulet.2014.10.037. Epub 2014 Oct 28. PMID: 25449871.
1: Zhang JX, Guo JM, Zhang TT, Lin HJ, Qi NS, Li ZG, Zhou JC, Zhang ZZ. Antiproliferative Phenothiazine Hybrids as Novel Apoptosis Inducers against MCF-7 Breast Cancer. Molecules. 2018 May 28;23(6). pii: E1288. doi: 10.3390/molecules23061288. PubMed PMID: 29843370. 2: Choudhary S, Silakari O, Singh PK. New Insights into Chemistry and Biological Potential of Thiazine Scaffold: A Review. Mini Rev Med Chem. 2018 Apr 27. doi: 10.2174/1389557518666180427150108. [Epub ahead of print] PubMed PMID: 29701151. 3: Leskovac A, Petrovic S, Lazarevic-Pasti T, Krstic M, Vasic V. Ruthenium(II)-N-alkyl phenothiazine complexes as potential anticancer agents. J Biol Inorg Chem. 2018 Apr 11. doi: 10.1007/s00775-018-1560-x. [Epub ahead of print] PubMed PMID: 29644470. 4: Loch JI, Bonarek P, Tworzydło M, Łazińska I, Szydłowska J, Lipowska J, Rzęsikowska K, Lewiński K. The engineered β-lactoglobulin with complementarity to the chlorpromazine chiral conformers. Int J Biol Macromol. 2018 Jul 15;114:85-96. doi: 10.1016/j.ijbiomac.2018.03.074. Epub 2018 Mar 16. PubMed PMID: 29555509. 5: Otręba M, Buszman E. Perphenazine and prochlorperazine induce concentration-dependent loss in human glioblastoma cells viability. Pharmazie. 2018 Jan 2;73(1):19-21. doi: 10.1691/ph.2018.7806. PubMed PMID: 29441946. 6: Schwab K, Frahm S, Horsley D, Rickard JE, Melis V, Goatman EA, Magbagbeolu M, Douglas M, Leith MG, Baddeley TC, Storey JMD, Riedel G, Wischik CM, Harrington CR, Theuring F. A Protein Aggregation Inhibitor, Leuco-Methylthioninium Bis(Hydromethanesulfonate), Decreases α-Synuclein Inclusions in a Transgenic Mouse Model of Synucleinopathy. Front Mol Neurosci. 2018 Jan 10;10:447. doi: 10.3389/fnmol.2017.00447. eCollection 2017. PubMed PMID: 29375308; PubMed Central PMCID: PMC5767730. 7: Zhang J, Ming C, Zhang W, Okechukwu PN, Morak-Młodawska B, Pluta K, Jeleń M, Akim AM, Ang KP, Ooi KK. 10H-3,6-Diazaphenothiazine induces G(2)/M phase cell cycle arrest and caspase-dependent apoptosis and inhibits cell invasion of A2780 ovarian carcinoma cells through the regulation of NF-κB and (BIRC6-XIAP) complexes. Drug Des Devel Ther. 2017 Oct 24;11:3045-3063. doi: 10.2147/DDDT.S144415. eCollection 2017. PubMed PMID: 29123378; PubMed Central PMCID: PMC5661483. 8: Varga B, Csonka Á, Csonka A, Molnár J, Amaral L, Spengler G. Possible Biological and Clinical Applications of Phenothiazines. Anticancer Res. 2017 Nov;37(11):5983-5993. Review. PubMed PMID: 29061777. 9: Sobczak A, Teżyk A, Szyndlarewicz J, Ziarniak J, Świątek P, Malinka W. New fluphenazine analogue with antimutagenic and anti-multidrug resistance activity-degradation profile and stability-indicating method. Med Chem Res. 2017;26(10):2443-2451. doi: 10.1007/s00044-017-1944-4. Epub 2017 Jun 15. PubMed PMID: 29051697; PubMed Central PMCID: PMC5628186. 10: de Oliveira SCPS, Monteiro JSC, Pires-Santos GM, Sampaio FJP, Soares AP, Soares LGP, Pinheiro ALB. LED antimicrobial photodynamic therapy with phenothiazinium dye against Staphylococcus aureus: An in vitro study. J Photochem Photobiol B. 2017 Oct;175:46-50. doi: 10.1016/j.jphotobiol.2017.08.029. Epub 2017 Aug 24. PubMed PMID: 28846934. 11: Ghashghaeinia M, Wesseling MC, Ramos E, Petkova-Kirova P, Waibel S, Lang E, Bissinger R, Alzoubi K, Edelmann B, Hosseinzadeh Z, Dreischer P, Shahvaroughi-Farahani A, Mrowietz U, Köberle M, Kaestner L, Bernhardt I, Martínez-Ruiz A, Wieder T, Lang F. Trifluoperazine-Induced Suicidal Erythrocyte Death and S-Nitrosylation Inhibition, Reversed by the Nitric Oxide Donor Sodium Nitroprusside. Cell Physiol Biochem. 2017;42(5):1985-1998. doi: 10.1159/000479838. Epub 2017 Aug 9. PubMed PMID: 28793283. 12: Fu DJ, Zhao RH, Li JH, Yang JJ, Mao RW, Wu BW, Li P, Zi XL, Zhang QQ, Cai HJ, Zhang SY, Zhang YB, Liu HM. Molecular diversity of phenothiazines: design and synthesis of phenothiazine-dithiocarbamate hybrids as potential cell cycle blockers. Mol Divers. 2017 Nov;21(4):933-942. doi: 10.1007/s11030-017-9773-4. Epub 2017 Aug 7. PubMed PMID: 28785928. 13: Pluta K, Jeleń M, Morak-Młodawska B, Zimecki M, Artym J, Kocięba M, Zaczyńska E. Azaphenothiazines - promising phenothiazine derivatives. An insight into nomenclature, synthesis, structure elucidation and biological properties. Eur J Med Chem. 2017 Sep 29;138:774-806. doi: 10.1016/j.ejmech.2017.07.009. Epub 2017 Jul 8. Review. PubMed PMID: 28734245. 14: Brem B, Gal E, Găină L, Silaghi-Dumitrescu L, Fischer-Fodor E, Tomuleasa CI, Grozav A, Zaharia V, Filip L, Cristea C. Novel Thiazolo[5,4-b]phenothiazine Derivatives: Synthesis, Structural Characterization, and In Vitro Evaluation of Antiproliferative Activity against Human Leukaemia. Int J Mol Sci. 2017 Jun 26;18(7). pii: E1365. doi: 10.3390/ijms18071365. PubMed PMID: 28672876; PubMed Central PMCID: PMC5535858. 15: Sellamuthu S, Singh M, Kumar A, Singh SK. Type-II NADH Dehydrogenase (NDH-2): a promising therapeutic target for antitubercular and antibacterial drug discovery. Expert Opin Ther Targets. 2017 Jun;21(6):559-570. doi: 10.1080/14728222.2017.1327577. Epub 2017 May 15. Review. PubMed PMID: 28472892. 16: Oliva CR, Zhang W, Langford C, Suto MJ, Griguer CE. Repositioning chlorpromazine for treating chemoresistant glioma through the inhibition of cytochrome c oxidase bearing the COX4-1 regulatory subunit. Oncotarget. 2017 Jun 6;8(23):37568-37583. doi: 10.18632/oncotarget.17247. PubMed PMID: 28455961; PubMed Central PMCID: PMC5514931. 17: Ghorab MM, Alsaid MS, Samir N, Abdel-Latif GA, Soliman AM, Ragab FA, Abou El Ella DA. Aromatase inhibitors and apoptotic inducers: Design, synthesis, anticancer activity and molecular modeling studies of novel phenothiazine derivatives carrying sulfonamide moiety as hybrid molecules. Eur J Med Chem. 2017 Jul 7;134:304-315. doi: 10.1016/j.ejmech.2017.04.028. Epub 2017 Apr 15. PubMed PMID: 28427017. 18: Klutzny S, Lesche R, Keck M, Kaulfuss S, Schlicker A, Christian S, Sperl C, Neuhaus R, Mowat J, Steckel M, Riefke B, Prechtl S, Parczyk K, Steigemann P. Functional inhibition of acid sphingomyelinase by Fluphenazine triggers hypoxia-specific tumor cell death. Cell Death Dis. 2017 Mar 30;8(3):e2709. doi: 10.1038/cddis.2017.130. PubMed PMID: 28358364; PubMed Central PMCID: PMC5386533. 19: Steinberg AC, Schimpf MO, White AB, Mathews C, Ellington DR, Jeppson P, Crisp C, Aschkenazi SO, Mamik MM, Balk EM, Murphy M. Preemptive analgesia for postoperative hysterectomy pain control: systematic review and clinical practice guidelines. Am J Obstet Gynecol. 2017 Sep;217(3):303-313.e6. doi: 10.1016/j.ajog.2017.03.013. Epub 2017 Mar 27. Review. PubMed PMID: 28351670. 20: Hong WD, Gibbons PD, Leung SC, Amewu R, Stocks PA, Stachulski A, Horta P, Cristiano MLS, Shone AE, Moss D, Ardrey A, Sharma R, Warman AJ, Bedingfield PTP, Fisher NE, Aljayyoussi G, Mead S, Caws M, Berry NG, Ward SA, Biagini GA, O'Neill PM, Nixon GL. Rational Design, Synthesis, and Biological Evaluation of Heterocyclic Quinolones Targeting the Respiratory Chain of Mycobacterium tuberculosis. J Med Chem. 2017 May 11;60(9):3703-3726. doi: 10.1021/acs.jmedchem.6b01718. Epub 2017 Apr 25. PubMed PMID: 28304162.