Electronic Effects of para-Substituents on the Local Anesthetic Activity of 2-Diethylaminoethyl Benzoate and Related Compounds<sup>1a,1b</sup>

Galinsky, Alvin M.; Gearien, James E.; Perkins, Alfred J.; Susina, Stanley V.

doi:10.1021/jm00339a024

Cited by 19 publications

(6 citation statements)

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“…Now the correlation expressed by this equation expresses that more a hydrophobic and electron-donating group will lead to a more pronounced increase in the activity. These compounds were studied by Galinsky et al 45 These authors related the activity with the infrared absorption frequency of the substituent which is of course related to a. They also noted that the more electron-releasing group gave the more pronounced effect on the activity.…”

Section: Osar Results and Discussionmentioning

confidence: 99%

QSAR (quantitative structure-activity relationship) studies on local anesthetics

Gupta¹

1991

Chem. Rev.

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Section: Osar Results and Discussionmentioning

confidence: 99%

QSAR (quantitative structure-activity relationship) studies on local anesthetics

Gupta¹

1991

Chem. Rev.

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“…(42) , who used the infrared car bonyl absorption frequency as a measure of the reactivity of the carbonyl group in a series of diethylaminoethyl para-substituted benzoates, cinna mates, and �-phenyl propionates. In general, a good correlation existed be tween the infrared spectra and the local anesthetic potency.…”

Section: Relations Between Structure and Activitymentioning

confidence: 99%

On the Mode of Action of Local Anesthetics

Ritchie¹,

Greengard²

1966

Annu. Rev. Pharmacol.

236

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Local anesthetics possess the specific ability to bl ock conduction in nerve in a reversible ma nner and in low concentration. The reactions that occur in the ner ve membrane that allow local anesthetics to achieve this effect are still not clearly defi ned. Howe ver , with the re cent increa se in our knowledge of the nature of the nerve impul se , some idea of the mode of action of local anesthetics is be ginning to form. Measurements of me m brane potentials and ionic move me nt s have strong ly suggested that local anesthetics block cond uct ion by inter fe ring with the sodium and potassium conductance cha ng es that are fundamental to the generation of the nerve impulse . Other studies have indicated that local anesthetic molecule s achieve this conduction block in the form of ca ti ons. Furthermore, studies of structure-activity relations have suggeste d someth ing of the chemical na ture of the re ce ptor in the nerve membrane and the method of interac tion of this receptor with the local anesthetic molecule . Finally, studies of the be ha vior of loca l anesthetics in model systems have suggested a phys icochemical ba sis for the mode of action of local anesthetics on the ne rve membrane. These various aspects of local anesthetic action will be g iven particular emphasis in this review. Many other, perhaps equally important, aspects will be neglected, and the interested reader is there fore referred to the many comprehensive reviews on local anesthetics that have appeared in the last decade (4,14,24,25,56,73,94,104,106,108). ELECTROPHYSIOLOGICAL EFFECTS OF LOCAL ANESTHETICSThe work of Hodgkin, Huxley, Keynes, and ot hers [see (52)] has led in recent year s to a better under standing of the nature of the nerve im pulse . In consequence , it is now possible to expla in the action of local an esthet ics within the fra me wor k of the ionic theory of nervous act ivity .Active nerve membrane.-Local anesthetics increase the threshold for ele ctr ical excitat ion in nerve , slow pr opagation of the impul se, reduce the rate of rise of the action pote nt ial, and eventually bl ock conduct ion [e.g. (85)]. They do this by inter fer ing with the pr oce ss fundamental to the gen eration of the nerve action pote ntial, name ly the large transient rise in the permeability of the me mbrane to sodium ions that is produced by a slight de pola rization of the me mbrane. Taylor (99), Shanes et al. (85), and, more re ce ntly, Blaustein & Goldman (19) used the voltage-clamp me thod to study 1 The survey of th e literature pertaining to this review was concluded in Octo ber 1965. 405 Annu. Rev. Pharmacol. 1966.6:405-430. Downloaded from www.annualreviews.org Access provided by Queens University -Kingston (Canada) on 03/08/15. For personal use only. Quick links to online content Further ANNUAL REVIEWS

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“…Pharmacology1-The epimers (IVa and IVb) were evaluated with regard to (a) conduction block anesthesia in rats (see Table I) (16); (b) infiltration anesthesia in guinea pigs (see Table 11) (17); (c) their irritation properties in rabbits (see Table 111) (16); and (6) conduction-block anesthesia on isolated intact frog nerves (see Fig. 1…”

Section: Discussionmentioning

confidence: 99%

Conformational Aspects of Local Anesthetics

Boots

1969

Journal of Pharmaceutical Sciences

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Electronic Effects of para-Substituents on the Local Anesthetic Activity of 2-Diethylaminoethyl Benzoate and Related Compounds^1a,1b

Abstract: The infrared spectra of a number of diethylaminoethvl -suhstifuted benzoates, cirmamates and p-phenyl-pr

Cited by 19 publications

References 1 publication

QSAR (quantitative structure-activity relationship) studies on local anesthetics

QSAR (quantitative structure-activity relationship) studies on local anesthetics

On the Mode of Action of Local Anesthetics

Conformational Aspects of Local Anesthetics

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Electronic Effects of para-Substituents on the Local Anesthetic Activity of 2-Diethylaminoethyl Benzoate and Related Compounds1a,1b

Abstract: The infrared spectra of a number of diethylaminoethvl -suhstifuted benzoates, cirmamates and p-phenyl-pr

Cited by 19 publications

References 1 publication

QSAR (quantitative structure-activity relationship) studies on local anesthetics

QSAR (quantitative structure-activity relationship) studies on local anesthetics

On the Mode of Action of Local Anesthetics

Conformational Aspects of Local Anesthetics

Contact Info

Product

Resources

About

Electronic Effects of para-Substituents on the Local Anesthetic Activity of 2-Diethylaminoethyl Benzoate and Related Compounds^1a,1b