CAS 51-83-2 Carbamylcholine Chloride - Catalysts / Alfa Chemistry

Synonyms

FT-0623453; Moryl; MFCD00012011; Vasoperif; NSC-32865; Choline, carbamate; Lentin; D00524; 2-(trimethylazaniumyl)ethyl carbamate chloride; SW197107-3;

IUPAC Name

2-carbamoyloxyethyl(trimethyl)azanium;chloride;

Molecular Weight

182.648g/mol

Molecular Formula

C6H15ClN2O2;

Canonical SMILES

C[N+](C)(C)CCOC(=O)N.[Cl-];

InChI

InChI=1S/C6H14N2O2.ClH/c1-8(2,3)4-5-10-6(7)9;/h4-5H2,1-3H3,(H-,7,9);1H;

InChI Key

AIXAANGOTKPUOY-UHFFFAOYSA-N;

Melting Point

392 to 401 ° F (EPA, 1998);208-210;200-203 deg C, some decomposition;

Solubility

1 g in 1 ml water;1 g in 50 ml alcohol;Very slightly sol in dehydrated alcohol, more readily sol on boiling;1 g in 10 ml methanol;Practically insol in chloroform, ether, acetone;

Storage

Desiccate at RT

Color Form

Hard prismatic crystals;White or faintly yellow crystals or crystalline powder;

Complexity

117

Covalently-Bonded Unit Count

Decomposition

When heated to decomposition it emits ... very toxic fumes of /hydrogen chloride, ammonia and nitrogen oxides/.;

EC Number

200-127-3

Exact Mass

182.082g/mol

H-Bond Acceptor

H-Bond Donor

Heavy Atom Count

Monoisotopic Mass

182.082g/mol

NSC Number

755919

Odor

Odorless or has a slight amine-like odor;

Other Experimental

Hygroscopic;Ophthalmic soln of carbachol has a pH of 5-7; the commercially available intraocular injection has a pH of 6.5-7.5 /Soln/;Chlorocresol (0.025 to 0.1%) and chlorbutol (0.5%) were incompatible with a soln of carbachol (0.8%) and sodium chloride (0.69%), very slight precipitates forming on heating and increasing on standing. /Soln/;Incompatible with alkalies, iodine, and silver salts;

Rotatable Bond Count

Stability

The aqueous soln is stable even when heated.;

Topological Polar Surface Area

52.3A^2

UNII

8Y164V895Y

UN Number

2811

Application

Carbamylcholine Chloride serves as a potent cholinergic receptor agonist, uniquely characterized by a carbamino functional group that renders it resistant to hydrolysis by cholinesterases, contrasting with acetylcholine and methacholine. This resistance results in a significantly slower rate of hydrolysis, extending its functionality as both an ophthalmic solution for glaucoma treatment and during eye surgeries. By stimulating muscarinic and nicotinic receptors, Carbamylcholine Chloride mirrors the pharmacological actions of acetylcholine, promoting effects such as vasodilation, heart rate reduction, and enhanced contraction of smooth muscles. It stimulates glands and autonomic responses, albeit with a narrow scope of use restricted primarily to ophthalmological and specific post-surgical applications due to its powerful effects. In practical applications, its utility extends to certain veterinary uses, particularly for treating colic in horses. Notably, its efficacy in lowering intraocular pressure and constricting pupils highlights its therapeutic relevance for severe chronic glaucoma. Formulated as prismatic crystals or powder, it is odorless but may develop a faint odor upon prolonged exposure. As a carbamate ester, it shares reactivity traits with amides yet is more chemically active, necessitating careful handling to avoid hazardous reactions with incompatible substances.

December 03, 2024

Carbamylcholine Chloride: Reliable Cholinergic Agonist for Research

I effectively used Carbamylcholine Chloride in my research on cholinergic receptors. Its resistance to cholinesterases was crucial for studying prolonged receptor activation and its antiapoptotic effects in neuronal cells were noteworthy.