Mequitazine

• CAT Number: R009381
• CAS Number: 29216-28-2
• Molecular Formula: C20H22N2S
• Molecular Weight: 322.47
• Purity: ≥95%
• Storage: Room temperature
• IUPAC Name: 10-(1-azabicyclo[2.2.2]octan-3-ylmethyl)phenothiazine
• InChI: InChI=1S/C20H22N2S/c1-3-7-19-17(5-1)22(18-6-2-4-8-20(18)23-19)14-16-13-21-11-9-15(16)10-12-21/h1-8,15-16H,9-14H2
• InChIKey: HOKDBMAJZXIPGC-UHFFFAOYSA-N
• SMILES: C1CN2CCC1C(C2)CN3C4=CC=CC=C4SC5=CC=CC=C53

Mequitazine is a potent histamine H1 antagonist or antihistamine. It competes with histamine for the normal H1-receptor sites on effector cells of the gastrointestinal tract, blood vessels and respiratory tract. Mequitazine provides effective, temporary relief of sneezing, watery and itchy eyes, and runny nose due to hay fever and other upper respiratory allergies.

Reference

1:On-the-road driving performance after use of the antihistamines mequitazine and l-mequitazine, alone and with alcohol. van der Sluiszen NN, Vermeeren A, Jongen S, Theunissen EL, van Oers AC, Van Leeuwen CJ, Maret A, Desforges C, Delarue A, Ramaekers JG.Psychopharmacology (Berl). 2016 Sep;233(18):3461-9. doi: 10.1007/s00213-016-4386-7. Epub 2016 Aug 4. PMID: 27488192 Free PMC Article2:Quantification of mequitazine in human plasma by gas chromatography- quadrupole mass spectrometry and its application to a human pharmacokinetic study. Ahn SH, Maeng HJ.Biomed Chromatogr. 2016 Apr;30(4):574-8. doi: 10.1002/bmc.3585. Epub 2015 Sep 20. PMID: 26268745 3:Asymmetric synthesis of (+)-mequitazine from quinine. Leroux S, Larquetoux L, Nicolas M, Doris E.Org Lett. 2011 Jul 1;13(13):3549-51. doi: 10.1021/ol2012567. Epub 2011 Jun 9. PMID: 21657243 4:Expedient synthesis of mequitazine an antihistaminic drug by palladium catalyzed allylic alkylation of sodium phenothiazinate. Gonnot V, Nicolas M, Mioskowski C, Baati R.Chem Pharm Bull (Tokyo). 2009 Nov;57(11):1300-2. PMID: 19881287 Free Article5:Photodegradation and photostability-indication of mequitazine. Abdel-Moety EM, Ibrahim MA, Rezk MR.Spectrochim Acta A Mol Biomol Spectrosc. 2009 Oct 15;74(3):740-5. doi: 10.1016/j.saa.2009.08.006. Epub 2009 Aug 12. PMID: 19729339 6:Pipette tip solid-phase extraction and gas chromatography-mass spectrometry for the determination of mequitazine in human plasma. Kumazawa T, Hasegawa C, Lee XP, Marumo A, Shimmen N, Ishii A, Seno H, Sato K.Talanta. 2006 Sep 15;70(2):474-8. doi: 10.1016/j.talanta.2006.02.059. Epub 2006 May 2. PMID: 18970795 7:[Efficiency of mequitazine in the treatment of allergic rhinitis and chronic urticaria in children. A bibliographic systematic review]. Martín JP, Martinez HG, Pérez GL, Manzur JN.Rev Alerg Mex. 2008 Jan-Feb;55(1):3-9. Review. Spanish. PMID: 18697448 8:[Symptomatic treatment of allergic rhinitis with mequitazine (Primalan)]. Pérez Martín J.Rev Alerg Mex. 2006 Nov-Dec;53(6):195-200. Spanish. PMID: 17361752 9:[Efficacy of mequitazine (Primalan) on the relief of symptoms of allergic rhinoconjunctivitis in children. Documented clinical experience]. Ramírez Chanona N, del Rio Navarro BE, Pérez Martín J.Rev Alerg Mex. 2005 Nov-Dec;52(6):221-5. Spanish. PMID: 16568706 10:Repeated-dose effects of mequitazine, cetirizine and dexchlorpheniramine on driving and psychomotor performance. Theunissen EL, Vermeeren A, Ramaekers JG.Br J Clin Pharmacol. 2006 Jan;61(1):79-86. PMID: 16390354 Free PMC Article