Isopropyl hydrazide

Considerable information about serotonin metabolism has been learned from the action of monoamine oxidase inhibitors. One of the first of these compounds to be discovered was l-isonicotinyl-2-isopropyl hydrazide (Marsilid) 376) Many other compounds have since been discovered that inhibit monoamine oxidase both in vHxo and in vivo 368). The outcome of the studies with monoamine oxidase inhibitors has been to show that when the enzyme is inhibited there is a diminished formation of 5-hydroxyindoleacetic acid and serotonin is converted to the 0-glucuronide and excreted in rodents. In man there is little formation of serotonin glucuro-nide. The fate of serotonin in man under these conditions is not known definitely, although serotonin-O-sulfate has been observed in carcinoid patients. Serotonin may also be methylated to yield W-methyl-serotonin 368). 

Bromonaphthalene has been reduced to naphthalene in good yield by hydrogenation over Raney nickel in methanolic potassium hydroxide, by triphenyltin hydride in benzene, by magnesium in isopropyl alcohol, by sodium hydrazide and hydrazine in ether, and by copper(I) acetate in pyridine. ... 

Kelly MG et al Comparative carcinogenic-ity of -isopropyl- -(2 -methylhydrazino)-p-tolu-amide HCl (procarbazine hydrochloride), its degradation products, other hydrazines, and isonicotinic acid hydrazide. J Natl Cancer Inst 42 337-344, 1969... 

Hydrazines. The hydrazines have only historic significance. The entire group of MAOIs was discovered through the euphoric side effect of isoniazid (8.36, isonicotinyl-hydrazide), a successful antituberculotic drug introduced in 1952. Iproniazid (8.37) is the corresponding isopropyl derivative. All of the hydrazides are highly hepatotoxic, and are no longer available. 

Oils have been pre-eminent in grass killing, but with the introduction of isopropyl AT-phenyl carbamates, trichloroacetates, and maleic hydrazide, satisfactory... 

Methyl acrylate, 28.0 g (0.4 mol) was added dropwise during one hour to a solution containing 54.8 g (0.4 mol) of isonicotinic acid hydrazide (isoniazid) and 10 ml of glacial acetic acid in 400 ml of tertiary butyl alcohol. The resulting solution then was heated for 18 hours on a steam bath. Concentration of the reaction mixture to 100 ml yielded 13.0 g of unreacted isonicotinic acid hydrazide. The filtrate was concentrated to a thick syrup which was triturated with anhydrous ether and recrystallized from isopropyl alcohol MP 87°C to 88.5°C. Elemental analysis of the product gave 1-isonicotinyl-2-(p-carbomethoxyethyl)hydrazine. 

Thus, the hydrazide or its azo analogue not only plays a key-role in the catalytic cycle as a hydrogen acceptor and a reductant for the copper catalyst, but it also acts as an acyl transfer reagent generating competitively the undesired mixed carbonate 20. This by-product presumably originates from the inter- or intra-molecular nucleophilic attack of the alcohol on either the copper-hydrazide or azo complexes 13 or 18 respectively, resulting ultimately in the deactivation of the catalyst. To minimize this undesired trans-acylation reaction, steri-cally demanding azo-derivatives were tested (Fig. 7). Whilst di-isopropyl... 

Methyl-phenyl- -ethylester XII/1, 249 E2, 235 Methyl-phenyl- -hydrazid E2, 235 Methyl-phenyl- -(2-isopropyl-5-methyl-cyclo-hexylester) E2, 33... 

Harnstoif l,l-Diethyl-3-(2-methoxy-phenyl)- E4, 340 (Cl - NR2) Isoquinolin 2-Amino-6,7-dimethoxy-1 -methyl-1,2,3,4-tetrahydro-E16a, 501 (N-N-Aufbau) Kohlensaure -ethylester-[2-(4-isopropyl-phenyl)-hydrazid]... 

CARBAMIC ACID HYDRAZIDE see HGUOOO CARBAvnC ACID, ISOPROPYL ESTER see lOJOOO CARBAiMIC ACID, N-METHYL-, 3-DIETHYLARSINOPHENYL ESTER, METHIODIDE see MID900... 

SUCCINIC ACID DINITRILE see SNEOOO SUCCINIC ACID, HYDROXY- see MANOOO SUCCINIC ACID, O-ISOPROPYL-O -TRIBUTYLSTANNYL ESTER see TIE600 SUCCINIC ACID PEROXIDE (DOT) see SNC500 SUCCINIC ANHYDRIDE see SNCOOO SUCCINIC-1,1-DIMETHYL HYDRAZIDE see DQD400 SUCCINIC DINITRILE see SNEOOO SUCCINIC PEROXIDE see SNC500 SUCCINODINITRILE see SNEOOO... 

Thin-layer Chromatography. - Fourteen newly-synthesised organophos-phorus compounds have been separated by TLC, and a study made of their Rf values and structures for the aryloxyphenylthiophosphonyl hydrazides. When electron-donor solvents were used as mobile-phase, there were carbonyl displacement effects and the order of Rf values was reversed. In another study (by HPTLC), a correlation between the molecular structures of sixteen O-ethyl, N-isopropyl phosphoro(thioureido)thioates and their observed Rf values has been checked against a computer-assisted Rf prediction system for these... 

Isonicotinic acid hydrazide (isoniazid) and its N-isopropyl analog, iproniazid, were used as antitubercular drugs in the early 1950s. Independent reports showed that iproniazid (but not isoniazid) exhibited CNS stimulant properties in TB patients and had the ability to inhibit the enzyme MAO. Reports showed that the expected depressant effect of reserpine in animals could be prevented (reversed ) by pretreatment with iproniazid and resulted in CNS stimulation. In fact, NE s and 5-HT s neuronal depletion produced by reserpine was actually blocked by this pretreatment. This work, then, led to the proposal that the clinical antidepressant efficacy of iproniazid (and related MAO inhibitors synthesized in the interim) resulted from the increased levels of NE and 5-HT, which were allowed to rise because of MAO inhibition. Many other hydrazine and hydrazide variants were soon introduced into clinical use. 

After the discovery that ortho-biphenyl substituted hydrazide compounds [5] had acaricidal activity in the pesticide discovery screen (Table 30.2.3) several hundred - structurally diverse - biphenyl-substituted carbazate analogs were synthesized, and, in an optimization process using a bioassay with the two spotted spider mite (Tetranychus urticae Koch), isopropyl-2-(4-methoxy[l,l -biphenyl]-3-yl) hydrazine carboxylate (bifenazate) [3, 8] was identified as the most advantageous compound. 

No products arising from ring transformations occurred upon photolysis or pyrolysis of perfluoro-(2,4,S,6-tetraisopropylpyrimidine) (256). Hydrolysis (aq. H2SO4 at 150 °C) of tetrafluoropyridazine (270) yields initially 3,4,5-trifluoro-l -pyridazine-6-one (271) and then difluoromaleic hydrazide (272) that of perfluoro-(4,5-di-isopropyIpyridazine) (273) yields a mixture of pyridazone (271) and hydrazide (272), and then bis(heptafluorO isopropyl)maleic anhydride (274) at 210 °C (Scheme 55). ... 

Hydrazide cryst. from 70% EtOH. M.p. 141°. Sol. MeOH, EtOH, propyl alcohd, isopropyl alcohol, amyl alcohm, CHCl,. Less sol. C,He, toluene, xylene, chlorobenzene. Picrate prisms from EtOH. M.p. 216°. 

Diphenylphosphinyl hydrazide and isopropyl isothiocyanate refluxed 1 hr. in toluene l-diphenylphosphinyl-4-isopropylthiosemicarbazide. Y 92.8%. F. e., also 4-phosphinylthiosemicarbazides, s. H.-J. Jahns, Z. Chem. 10, 435 (1970) l-phosphinyl-4-acylthiosemicarbazides cf. ibid. 10, 465. 

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