Miotine

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Miotine
Miotine.png
Names
IUPAC name
[3-[1-(Dimethylamino)ethyl]phenyl] N-methylcarbamate
Identifiers
3D model (JSmol)
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C12H18N2O2/c1-9(14(3)4)10-6-5-7-11(8-10)16-12(15)13-2/h5-9H,1-4H3,(H,13,15) X mark.svgN
    Key: KQOUPMYYRQWZLI-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C12H18N2O2/c1-9(14(3)4)10-6-5-7-11(8-10)16-12(15)13-2/h5-9H,1-4H3,(H,13,15)
    Key: KQOUPMYYRQWZLI-UHFFFAOYAX
  • CC(C1=CC(=CC=C1)OC(=O)NC)N(C)C
Properties
C12H18N2O2
Molar mass 222.288 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Miotine is an anticholinesterase drug. Miotine was the first synthetic carbamate that was used clinically. [1]

Unlike the miotine analog neostigmine, it doesn't have a quaternary ammonium group to give it a permanent positive charge. It can exist as an uncharged free base which could allow it to cross the blood–brain barrier and cause unwanted central nervous system (CNS) side effects. [2]

Miotine equilibrium Miotineeq2.png
Miotine equilibrium

See also

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Neostigmine

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Physostigmine

Physostigmine is a highly toxic parasympathomimetic alkaloid, specifically, a reversible cholinesterase inhibitor. It occurs naturally in the Calabar bean and the Manchineel tree.

Pyridostigmine

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Vecuronium bromide

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Glycopyrronium bromide

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Rocuronium bromide Chemical compound

Rocuronium bromide is an aminosteroid non-depolarizing neuromuscular blocker or muscle relaxant used in modern anaesthesia to facilitate tracheal intubation by providing skeletal muscle relaxation, most commonly required for surgery or mechanical ventilation. It is used for standard endotracheal intubation, as well as for rapid sequence induction (RSI).

Ogilvie syndrome Medical condition

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Sugammadex

Sugammadex, sold under the brand name Bridion, is a medication for the reversal of neuromuscular blockade induced by rocuronium and vecuronium in general anaesthesia. It is the first selective relaxant binding agent (SRBA).

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Acetylcholinesterase inhibitor

Acetylcholinesterase inhibitors (AChEIs) also often called cholinesterase inhibitors, inhibit the enzyme acetylcholinesterase from breaking down the neurotransmitter acetylcholine into choline and acetate, thereby increasing both the level and duration of action of acetylcholine in the central nervous system, autonomic ganglia and neuromuscular junctions, which are rich in acetylcholine receptors. Acetylcholinesterase inhibitors are one of two types of cholinesterase inhibitors; the other being butyryl-cholinesterase inhibitors. Acetylcholinesterase is the primary member of the cholinesterase enzyme family.

Postoperative residual curarization Medical condition

Postoperative residual curarization (PORC) or residual neuromuscular blockade (RNMB) is a residual paresis after emergence from general anesthesia that may occur with the use of neuromuscular-blocking drugs. Today residual neuromuscular blockade is defined as a train of four ratio of less than 0.9 when measuring the response to ulnar nerve stimulation at the adductor pollicis muscle using mechanomyography or electromyography. A meta-analysis reported that the incidence of residual neuromuscular paralysis was 41% in patients receiving intermediate neuromuscular blocking agents during anaesthesia. It is possible that > 100,000 patients annually in the USA alone, are at risk of adverse events associated with undetected residual neuromuscular blockade. Neuromuscular function monitoring and the use of the appropriate dosage of sugammadex to reverse blockade produced by rocuronium can reduce the incidence of postoperative residual curarization. In this study, with usual care group receiving reversal with neostigmine resulted in a residual blockade rate of 43%.

T-1123 Chemical compound

T-1123 is a carbamate-based acetylcholinesterase inhibitor. It was investigated as a chemical warfare agent starting in 1940. It does not go through the blood-brain barrier due to the charge on quaternary nitrogen. The antidote is atropine. T-1123 is a quaternary ammonium ion. A phenyl carbamate ester is bonded in the meta position to the nitrogen on a diethylmethyl amine. The chloride salt of T-1123 is TL-1299.

TL-1238 Chemical compound

TL-1238 is an extremely potent carbamate acetylcholinesterase inhibitor. It has been shown to be more potent than neostigmine.

Ro 3-0412 is an acetylcholinesterase inhibitor. It is the organophosphate analog of neostigmine.

TL-599 Chemical compound

TL-599, also known as SB-8, is an extremely potent carbamate acetylcholinesterase inhibitor.

References

  1. "Archived copy" (PDF). Archived from the original (PDF) on 2009-05-09. Retrieved 2008-01-04.CS1 maint: archived copy as title (link)
  2. "An introduction to drugs,their action and discovery" (PDF).