Neostigminmethylsulfat

Bezeichnung:Neostigminmethylsulfat

CAS-Nr51-60-5

Englisch Name:Neostigmine Methyl Sulfate

CBNumberCB7853724

SummenformelC12H19N2O2.CH3O4S

Molgewicht334.39

MOL-Datei51-60-5.mol

Synonyma

Neostigminmetilsulfat

Neostigminmethylsulfat

Neostigminmethylsulfat physikalisch-chemischer Eigenschaften

Schmelzpunkt	175-177 °C(lit.)
storage temp.	-20°C
Löslichkeit	H₂O: 1 g/mL
Aggregatzustand	powder
Farbe	white
Wasserlöslichkeit	1g/10mL
Merck	14,6464
InChI	InChI=1S/C12H19N2O2.CH4O4S/c1-13(2)12(15)16-11-8-6-7-10(9-11)14(3,4)5;1-5-6(2,3)4/h6-9H,1-5H3;1H3,(H,2,3,4)/q+1;/p-1
InChIKey	OSZNNLWOYWAHSS-UHFFFAOYSA-M
SMILES	C1(OC(=O)N(C)C)C=CC=C([N+](C)(C)C)C=1.S([O-])(=O)(=O)OC
CAS Datenbank	51-60-5(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	T+
R-Sätze:	28-36/37/38-42/43-26/27/28
S-Sätze:	36-45-36/37/39-28A
RIDADR	UN 2811 6.1/PG 2
WGK Germany	3
RTECS-Nr.	CY1225000
HazardClass	6.1(a)
PackingGroup	II
HS Code	29242990
Toxizität	LD50 in mice (mg/kg): 0.16 i.v.; 0.42 s.c.; 7.5 orally, (Randall, Lehmann)

Gefahreninformationscode (GHS)

Neostigmine Methyl Sulfate Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R28:Sehr giftig beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R42/43:Sensibilisierung durch Einatmen und Hautkontakt möglich.
R26/27/28:Sehr giftig beim Einatmen, Verschlucken und Berührung mit der Haut.
S-Sätze Betriebsanweisung:
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Beschreibung
Neostigmine is a reversible inhibitor of acetylcholinesterase (AChE; K_d = 260 μM). In a rat model of knee joint inflammation, intrathecal administration of neostigmine (2-30 μg) increases endogenous acetylcholine levels and dose-dependently increases the latency of paw withdrawal in response to thermal and mechanical stimuli (ED₅₀s = 6.6 and 3.5 μg, respectively). Neostigmine (5 μg, i.p.) restores muscle action potentials in mice with a thymopoietin-induced neuromuscular block. Formulations containing neostigmine have been used in the treatment of myasthenia gravis and Ogilvie syndrome.
Chemische Eigenschaften
Crystalline Solid
Verwenden
Cholinergic; miotic; antidote (curare)
Definition
ChEBI: Neostigmine methyl sulfate is an arylammonium sulfate salt. It has a role as an EC 3.1.1.8 (cholinesterase) inhibitor.
Trademarks
Prostigmine (ICN).
Allgemeine Beschreibung
Neostigmine methylsulfate,(m-hydroxyphenyl)trimethylammonium methylsulfatedimethylcarbamate or the dimethylcarbamic ester of 3-hydroxyphenyltrimethylammoniummethylsulfate (Prostigminmethylsulfate), is a bitter, odorless, white, crystalline powder.It is very soluble in water and soluble in alcohol. Solutionsare stable and can be sterilized by boiling. The compound istoo hygroscopic for use in a solid form and thus is alwaysused as an injection. Aqueous solutions are neutral to litmus.
Clinical Use
The methylsulfate salt is used postoperatively as a urinarystimulant and in the diagnosis and treatment of myastheniagravis.
Synthese

16088-19-0

77-78-1

51-60-5

Example 9 Preparation of neostigmine methyl sulfate (general procedure) To a 250 mL four-necked round-bottomed flask was added 3-(dimethylamino)phenyldimethylcarbamate and acetone obtained in Example 1. Dimethyl sulfate (1.66 eq.) was added dropwise to the flask at room temperature. The reaction mixture was stirred overnight and then cooled to 5 °C to 10 °C and kept for 2 hours. This was followed by filtration and the filtrate was washed with isopropanol. The residue was dried under vacuum at room temperature to give the crude product neostigmine methyl sulfate. Purification was carried out by recrystallization from isopropanol. Yield: 85%. Properties: light yellow oil HPLC Purity: 99.21%.
läuterung methode
Crystallise the sulfate from EtOH or Me2CO (m 143-144o). Its solubility in H2O is ~10%. [Beilstein 13 III 939.] (It is cholinergic and highly TOXIC.)
Einzelnachweise
[1] Patent: WO2012/131699, 2012, A1. Location in patent: Page/Page column 15
[2] Pharmazie, 2001, vol. 56, # 2, p. 181 - 182
[3] Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation), 1941, vol. 14, p. 524,526
[4] Chem.Abstr., 1942, p. 3159
[5] Patent: CH208883, 1938,

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