Butamirate

Title: Butamirate
CAS Registry Number: 18109-80-3
CAS Name: a-Ethylbenzeneacetic acid 2-[2-(diethylamino)ethoxy]ethyl ester
Additional Names: 2-phenylbutyric acid 2-[2-(diethylamino)ethoxy]ethyl ester; 2-[2-(diethylamino)ethoxy]ethyl 2-phenylbutyrate; butamyrate
Molecular Formula: C18H29NO3
Molecular Weight: 307.43
Percent Composition: C 70.32%, H 9.51%, N 4.56%, O 15.61%
Literature References: Prepd by the esterification of phenylethylacetyl chloride with diethylaminoethoxyethanol: DE 1151515; Heusser, US 3349114 (1963, 1967, both to Hommel A.G.).
Properties: Practically colorless liquid with peculiar odor. bp1 140-155°. Practically insol in water. Very sol in alcohol, acetone, ether.
Boiling point: bp1 140-155°
Derivative Type: Citrate
CAS Registry Number: 18109-81-4
Manufacturers' Codes: Abbott 36581; HH-197
Trademarks: Acodeen (Hommel); Panatus (Krka); Sincodix (Beta); Sinecod (Zyma)
Molecular Formula: C18H29NO3.C6H8O7
Molecular Weight: 499.55
Percent Composition: C 57.70%, H 7.47%, N 2.80%, O 32.03%
Properties: White, hygroscopic crystals from acetone, mp 75°.
Melting point: mp 75°
Therap-Cat: Antitussive.
Keywords: Antitussive.
Butamisole Butanilicaine Butaperazine Butaverine Butazolamide

Butamirate
Butamirate.png
Systematic (IUPAC) name
2-(2-diethylaminoethoxy)ethyl 2-phenylbutanoate
Clinical data
AHFS/Drugs.com International Drug Names
Legal status  ?
Pharmacokinetic data
Protein binding 98%
Half-life 6 hours
Excretion 90% renal
Identifiers
CAS number 18109-80-3 YesY
ATC code R05DB13
PubChem CID 28892
ChemSpider 26873 YesY
UNII M75MZG2236 YesY
KEGG D07594 YesY
Chemical data
Formula C18H29NO3 
Mol. mass 307.428 g/mol
 YesY (what is this?)  (verify)

Butamirate (or brospamin) is a cough suppressant.[1]

A study found it to bind to the cough center in the medulla oblongata, more specifically the dextromethorphan-binding site in guinea pig brain with high affinity.[2]

As a 2-(2-diethylaminoethoxy)ethyl ester it is chemically related to oxeladin and pentoxyverine, which are in the same class. (Oxeladin has an additional ethyl group in its carboxylic acid, pentoxyverine has both ethyl groups of oxeladin replaced by one cyclopentyl in the same place.)