XVII.—Studies on the Pharmacological Action of Tetra-Alkyl-Ammonium Compounds: III. The Action of Methyl-Ethyl-Ammonium Chlorides

In view of the differences observed in the pharmacological action of tetra-methyl- and tetra-ethyl-ammonium chlorides, it seemed of interest to investigate the actions of the methyl-ethyl-ammonium compounds. The chlorides of these compounds—namely, tri-methyl-ethyl-ammonium chloride, di-methyl-di-ethyl-ammonium chloride, methyl-tri-ethyl-ammonium chloride—were kindly prepared for me by Dr J. E. Mackenzie, who has published the mode of preparation and the analysis of them.The only references I have found to the pharmacological action of the members of this series are brief statements by Tappeiner and Boehm. Tappeiner says that tri-ethyl-methyl-ammonium chloride, unlike tetra-methyl-ammonium chloride, does not produce temporary paralysis of the respiration; Boehm that tri-methyl-ethyl-ammonium chloride, like tetra-methyl-ammonium chloride, causes contracture of an isolated frog's muscle when a solution is applied to it.

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XII.—Studies on the Pharmacological Action of Tetra-Alkyl-Ammonium Compounds: II. The Action of Tetra-Ethyl-Ammonium Chloride

Transactions of the Royal Society of Edinburgh ◽

10.1017/s0080456800035985 ◽

1915 ◽

Vol 50 (2) ◽

pp. 379-396 ◽

Cited By ~ 8

Author(s):

C. R. Marshall

Keyword(s):

Ammonium Chloride ◽

Pharmacological Action ◽

Limited Extent ◽

Antagonistic Action ◽

Alkyl Ammonium ◽

Ammonium Compounds

The pharmacological action of tetra-ethyl-ammonium chloride has been investigated to a limited extent by Tillie, Santesson and Koraen, Tappeiner, Boehm, and Höber and Waldenberg, in the course of other researches. Tillie, and Santesson and Koraen, describe its action on frogs; Tappeiner merely states that it has no paralysing effect on the respiration of the rabbit; Boehm, and Höber and Waldenberg, refer only to its effect on the isolated frog's muscle. The descriptions of the action of the iodide, which has been investigated by Jordan, Brunton and Cash, Rothberger, Jacobj and Hagenberg, and Barger and Dale, in the course of other work, are also somewhat meagre. Brunton and Cash, and Jacobj and Hagenberg, describe its action on frogs, and Brunton and Cash its action on rabbits; but Jordan merely says that it produces on frogs a curare-like action but no muscarin effect, and Barger and Dale only state that it has no sympathomimetic action. The investigation of Rothberger was limited to its antagonistic action towards curarin.

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SiO2-POCl2 nano-particles promoted the synthesis of novel structure of alkyl 2-oxo-3,4-diaryloxazolidine-5-carboxylate derivatives

Letters in Organic Chemistry ◽

10.2174/1570178617999200528141627 ◽

2020 ◽

Vol 17 ◽

Author(s):

Mehdi Abaszadeh ◽

Seyyed Jalal Roudbaraki ◽

Hossein Yarahmadi ◽

Majid Ghashang

Keyword(s):

Nano Particles ◽

Methyl Ethyl ◽

Aniline Derivatives ◽

Ethyl Methyl ◽

Novel Structure ◽

Three Component Reaction ◽

High Yields

: Silica-POCl2 was used as the promoter for the three-component reaction of ethyl/methyl 3-phenyl glycidate, aniline derivatives, and dimethylcarbonate, leads to the synthesis of methyl/ethyl 2-oxo-4-phenyl-3-aryloxazolidine-5-carboxylate derivatives. The desired product was obtained in high yields.

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Behaviour of isomeric methyl ethyl and ethyl methyl halosuccinates under electron impact. Elimination of a halogen atom by a multi-step mechanism

Organic Mass Spectrometry ◽

10.1002/oms.1210260917 ◽

1991 ◽

Vol 26 (9) ◽

pp. 793-798 ◽

Cited By ~ 4

Author(s):

D. Bornstein ◽

A. Mandelbaum ◽

I. Vidavsky ◽

B. Domon ◽

D. Mueller ◽

...

Keyword(s):

Electron Impact ◽

Halogen Atom ◽

Methyl Ethyl ◽

Ethyl Methyl ◽

Step Mechanism ◽

Isomeric Methyl

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Structures, Intramolecular Rotation Barriers, and Thermochemical Properties of Methyl Ethyl, Methyl Isopropyl, and Methyltert-Butyl Ethers and the Corresponding Radicals

The Journal of Physical Chemistry A ◽

10.1021/jp022131n ◽

2003 ◽

Vol 107 (22) ◽

pp. 4531-4546 ◽

Cited By ~ 29

Author(s):

Chiung-Chu Chen ◽

Joseph W. Bozzelli

Keyword(s):

Thermochemical Properties ◽

Methyl Ethyl ◽

Ethyl Methyl ◽

Intramolecular Rotation

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On the Effects of Acetaldehyde, Ether Peroid, Ethyl Mercaptan, Ethyl Sulphid and Several Ketones???Di-Methyl, Ethyl Methyl and Di-Ethyl???When Added to Anesthetic Ether*

Anesthesia & Analgesia ◽

10.1213/00000539-192706000-00009 ◽

1927 ◽

Vol 6 (3) ◽

pp. 131???140 ◽

Cited By ~ 1

Author(s):

Wesley Bourne

Keyword(s):

Methyl Ethyl ◽

Ethyl Mercaptan ◽

Ethyl Methyl

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Permeability of Potassium Chloride, Tetra-Alkyl Ammonium Chloride and Dodecyl Amine Chloride in the Inside and at the Interface of the Gelatin Membrane

YAKUGAKU ZASSHI ◽

10.1248/yakushi1947.94.9_1170 ◽

1974 ◽

Vol 94 (9) ◽

pp. 1170-1177 ◽

Cited By ~ 3

Author(s):

MASAYUKI NAKAGAKI ◽

MASAKATSU YONESE

Keyword(s):

Potassium Chloride ◽

Ammonium Chloride ◽

Dodecyl Amine ◽

Alkyl Ammonium

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The protective action of hexane-1,6-BIS- (dimethyl-alkyl-ammonium) compounds against the organophosphate intoxication of acethylcholinesterase

European Journal of Pharmacology ◽

10.1016/0014-2999(67)90026-x ◽

1967 ◽

Vol 2 (1) ◽

pp. 67-68 ◽

Cited By ~ 13

Author(s):

H. Lüllmann ◽

F.K. Ohnesorge ◽

O. Wassermann

Keyword(s):

Protective Action ◽

Organophosphate Intoxication ◽

Alkyl Ammonium ◽

Ammonium Compounds

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II.—Studies on the Pharmacological Action of Tetra-Alkyl-Ammonium Compounds.

Transactions of the Royal Society of Edinburgh ◽

10.1017/s0080456800017257 ◽

1914 ◽

Vol 50 (1) ◽

pp. 17-40 ◽

Cited By ~ 3

Author(s):

C. R. Marshall

Keyword(s):

Ammonium Chloride ◽

Mucous Membrane ◽

Intravenous Injection ◽

Respiratory Muscles ◽

Pharmacological Action ◽

Nerve Endings ◽

Large Measure ◽

Nasal Mucous Membrane ◽

Hind Limbs ◽

Transient Paralysis

In a paper on “The Pharmacological Action of Protocatechyl-tropeine,” communicated to the Society in 1909, I drew attention to the fact that this substance, when injected intravenously in certain doses produces transient paralysis of the respiration; and I mentioned further that Tappeiner had described a similar temporary cessation of the respiration after the intravenous injection of certain quaternary isoxazol and pyrazol compounds, and of tetra-methyl-ammonium chloride, and Pohl, after the intravenous injection of some quaternary papaverine derivatives. Tappeiner came to the conclusion that the effect was due to stimulation of the terminations of the fifth cranial nerve in the nose; that it was, in fact, of the nature of a Kratschmer-Hering reflex, since he was unable, in the case of methyl-phenylisoxazol-methochloride, to produce cessation of the respiration after anæsthetising the nasal mucous membrane with cocaine; and Iodlbauer, working in Tappeiner's laboratory, also found that anæsthetisation of the nasal mucous membrane prevented the cessation of the respiration produced by tetra-methyl-ammonium chloride. Pohl, on the other hand, was able to produce this temporary paralysis of the respiration after section of the ophthalmic branches of both fifth nerves, and consequently he concluded that the effect was due to an action on the respiratory centre. I came to the same conclusion, since the effect was still obtained with protocatechyl-tropeine after section of both fifth nerves in the base of the skull and after section of both phrenic nerves, and was not synchronous with the effect on the circulation or with the paresis of the nerve-endings in the muscles of the hind limbs. Further work with tetra-methyl-ammonium chloride, however—my stock of protocatechyl-tropeiue being exhausted,—showed that the effect was in large measure peripheral and due to a transient paresis of the nerve-endings in the respiratory muscles.

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