Miotine

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

Miotine
Names

IUPAC name [3-[1-(Dimethylamino)ethyl]phenyl] N-methylcarbamate
Identifiers
CAS Number	4464-16-8^Y
3D model (JSmol)	Interactive image
ChemSpider	41955^N
KEGG	C11763^N
PubChem CID	46093
UNII	9Z3ZT09RRU^Y
CompTox Dashboard (EPA)	DTXSID10275489
InChI 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)^N Key: KQOUPMYYRQWZLI-UHFFFAOYSA-N^N 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
SMILES CC(C1=CC(=CC=C1)OC(=O)NC)N(C)C
Properties
Chemical formula	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).
N verify (what is ^YN ?)
Infobox references

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

References

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

Acetylcholine metabolism and transport modulators

Enzyme
(modulators)

ChAT	Inhibitors: 1-(-Benzoylethyl)pyridinium 2-(α-Naphthoyl)ethyltrimethylammonium 3-Chloro-4-stillbazole 4-(1-Naphthylvinyl)pyridine Acetylseco hemicholinium-3 Acryloylcholine AF64A B115 BETA CM-54,903 N,N-Dimethylaminoethylacrylate N,N-Dimethylaminoethylchloroacetate
AChE	Inhibitors: Reversible: Carbamates: Aldicarb Aminocarb Bendiocarb Bufencarb Carbaryl Carbendazim Carbetamide Carbofuran Carbosulfan Chlorbufam Chloropropham Dimetilan Ethienocarb Ethiofencarb Fenobucarb Formetanate Formparanate Methiocarb Methomyl Metolcarb Miotine Oxamyl Phenmedipham Pinmicarb Pirimicarb Propamocarb Propham Propoxur Thiofanox; Stigmines: Distigmine Eptastigmine Ganstigmine Neostigmine Phenserine Physostigmine Pyridostigmine Quilostigmine Rivastigmine Terestigmine; Others: Acotiamide Ambenonium Caffeine Donepezil EA-3990 EA-4056 Edrophonium Galantamine Huperzine A Ipidacrine Itopride Ladostigil Minaprine Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide) T-1123 TL-599 TL-1238 Tacrine Zanapezil Irreversible: Organophosphates: 2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate Acephate Anatoxin-a(S) Armine Azinphos-ethyl Azinphos-methyl BAY-29952 Bensulide Cadusafos Carbophenothion Chlorethoxyfos Chlorfenvinphos Chlorpyrifos Chlorpyrifos-methyl Coumaphos Crotylsarin Cyanophos Cyclosarin (GF) Demephion Demeton Demeton-S-methyl Dialifor Diazinon Dichlorvos Dicrotophos Diisopropyl fluorophosphate Diisopropylphosphate Dimefox Dimethoate Dimethyl 4-(methylthio)phenyl phosphate Dioxathion Disulfoton EA-2012 EA-2054 EA-2098 EA-2192 EA-2613 EA-3148 EA-4352 Echothiophate Ethylsarin (GE) Endothion Ethion Ethoprop Fenamiphos Fenitrothion Fenthion Fluorotabun Fonofos Formothion Fosthiazate GD-42 GH GT-45 GV Hexaethyl tetraphosphate Isofluorophate Isoxathion Leptophos Malaoxon Malathion Methamidophos Methidathion Methyl phenkapton Methylfluorophosphonylcholine (MFPCh) Metrifonate Mevinphos Mipafox Monocrotophos Naled Novichok agent Omethoate Oxydemeton-methyl Paraoxon Parathion Parathion-methyl Phorate Phosalone Phosfolan Phosmet Phosphamidon Phoxim Pirimiphos-methyl Profenofos Prothoate Ro 3-0340 Ro 3-0346 Ro 3-0347 Ro 3-0351 Ro 3-0352 Ro 3-0397 Ro 3-0411 Ro 3-0412 Ro 3-0417 Ro 3-0419 Ro 3-0422 Ro 3-0433 Sarin (GB) Schradan Soman (GD) Tabun (GA) Tebupirimfos Temefos Terbufos Tetrachlorvinphos Tetraethyl pyrophosphate Triazofos Tribufos Trichlorfon Trichloronate Tricresyl phosphate VE VG VM VP VS VR VX; Others: Demecarium Fasciculins (green mamba toxins) (1, 2, 3, 4) Onchidal (Onchidella binneyi) Methanesulfonyl fluoride Unsorted: α-Pinene α-Viniferin Affinine Affinisine Arisugacin A Bulbocapnine Conodurine Coronaridine Corydaline Corynoline Crimidine Cyclanoline Cymserine Harmaline Kobophenol A Lactucopicrin Lycorine Phosacetim Rosmarinic acid Stercuronium iodide Taspine Tetrahydrocannabinol Ungeremine Ungiminorine Dimethylcarbamoyl fluoride BW284C51 TMTFA Reactivators: Asoxime chloride Methoxime Obidoxime Pralidoxime Trimedoxime bromide
BChE	Inhibitors: Affinine Affinisine Conodurine Cymserine Ladostigil Profenamine (ethopropazine) Rivastigmine Tacrine ZINC-12613047 Many of the other AChE inhibitors listed above

Transporter
(modulators)

CHT	Inhibitors: Hemicholinium-3 (hemicholine) Triethylcholine Enhancers: Coluracetam
VAChT	Inhibitors: Vesamicol

Release
(modulators)

Inhibitors	SNAP-25 inactivators: Botulinum toxin (A, C, E) VAMP inactivators: Botulinum toxin (B, D, F, G) Others: Bungarotoxins (β-bungarotoxin, γ-bungarotoxin)
Enhancers	LPHN agonists: α-Latrotoxin Others: Atracotoxins (e.g., robustoxin, versutoxin) Crotoxin

See also: Receptor/signaling modulators • Muscarinic acetylcholine receptor modulators • Nicotinic acetylcholine receptor modulators

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