Phenothiazine nitration

Phenothiazine nitrated to its tetranitro derivative was used by the Germans during World War II as a component of a non-fusible explosive composition known under the name of Pressling . Monard, Ficheroulle and Fournier [45] found the compound to be phenothiazine tetranitrosulphoxide (I) (m. p. 368°C) ... 

Phenothiazines, nitrates Tricyclic antidepressants Decreased blood pressure... 

Authors are designed row sensitive and selective test-systems for analysis of heavy metals, active chlorine, phenols, nitrates, nitrites, phosphate etc. for analysis of objects of an environment and for control of ions Ee contents in the technological solutions of KH PO, as well as for testing some of pharmacological psychotropic daigs alkaloids (including opiates), cannabis as well as pharmaceutical preparations of phenothiazines, barbiturates and 1,4-benzodiazepines series too. 

Drugs that may interact with nitrates include alcohol, alteplase, aspirin, beta-blockers, calcium channel blockers, dihydroergotamine, heparin, nondepolarizing muscle relaxants, phenothiazines, phosphodiesterase inhibitors (eg, sildenafil, tadalafil, vardenafil), and vasodilators. 

Filiala Cluj. Studii Cercecari Chim 8, 303 (1957) St CA 54, 22657(1960) [Prepn of 1,3,7,9-Tetranitro phenothiazine-5-oxide, yel-orn ndls (from Nttrobenz), mp 354—55°, by. nitrating phenothiazine with a mixt of ni trie acid (d 1.50) St 20% oleum and heating on a w-bath for 20 mins]... 

Even the comparatively unreactive phenoxazine and phenothiazine systems undergo halogenation and nitration with ease and it is normal to prepare monosubstituted derivatives by stepwise procedures rather than by direct electrophilic attack. Indeed, the nitration of phenoxazine is uncontrollable and even N-acylphenoxazines afford a mixture of di- and tetra-nitro products (03CB475). Similarly phenothiazine and nitric acid produce a complex mixture of nitrated sulfoxides and sulfones. Chlorine in DMSO at 40 °C reacts with phenothiazine to yield 3,7-dichlorophenothiazine, whereas cupric chloride gives the 1,7-isomer (76JPR353). Direct bromination of phenoxazine produces a mixture of 3-bromo- and 3,7-dibromo-phenoxazines, while thionyl chloride affords the 1,3,7,9-tetrachloro derivative (60ZOB1893). 

The compound may be prepared in 70% yield by the nitration of phenothiazine with a mixture of 98% nitric acid and anhydrous sulphuric acid at 60°C. In addition to nitration, oxidation of the sulphur atom also takes place, resulting in the formation of the sulphoxide. 

Bemthsen [46], Kehrmann and co-workers [47] and Gilman and Shirley [48] also observed similar oxidation of the sulphur atom when nitrating phenothiazine... 

ANTIPSYCHOTICS-PHENOTHIAZINE, CLOZAPINE, PIMOZIDE NITRATES 1. T risk of antimuscarinic side-effects when isosorbide dinitrate is co administered with these drugs. 2.1 efficacy of sublingual nitrate tablets 1. Additive effect both of these drugs cause antimuscarinic side-effects 2. Antimuscarinic effects i saliva production, which i dissolution of the tablet 1. Warn patient of these effects 2. Consider changing the formulation to a sublingual nitrate spray... 

ANTIHISTAMINES-CHLORPHENAMINE, CYPROHEPTADINE, HYDROXYZINE 1. ANALGESICS - nefopam 2. ANTIARRHYTHMICS-disopyramide, propafenone 3. ANTIDEPRESSANTS-TCAs 4. ANTIMUSCARINICS - atropine, benzatropine, cydopentolate, dicydoverine, flavoxate, homat-ropine, hyosdne, orphenadrine, oxybutynin, procydidine, propantheline, tolterodine, trihexyphenidyl, tropicamide 5. ANTI PARKINSON S DRUGS -dopaminergics 6. ANTIPSY-CHOTICS - phenothiazines, dozapine, pimozide 7. MUSCLE RELAXANTS - baclofen 8. NITRATES - isosorbide dinitrate t risk of antimuscarinic side-effects. NB i efficacy of sublingual nitrate tablets... 

Recently the nitration of phenothiazine has been clarified and most of the controversy in the early literature over the structure and... 

Nitration of phenothiazine-5-oxide has not been thoroughly investigated however, using HNO3 d. 1.42, pure 3-nitropheno-thiazine-5-oxide can be obtained in good yield. 

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