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Antitussive
Caramiphen
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Caramiphen

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Caramiphen
Caramiphen.svg
Clinical data
Trade names Carafen
ATC code
  • None
Identifiers
  • 2-(Diethylamino)ethyl 1-phenylcyclopentanecarboxylate
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.000.922
Chemical and physical data
Formula C18H27NO2
Molar mass 289.419 g·mol−1
3D model (JSmol)
  • O=C(OCCN(CC)CC)C2(c1ccccc1)CCCC2
  • InChI=1S/C18H27NO2/c1-3-19(4-2)14-15-21-17(20)18(12-8-9-13-18)16-10-6-5-7-11-16/h5-7,10-11H,3-4,8-9,12-15H2,1-2H3
  • Key:OFAIGZWCDGNZGT-UHFFFAOYSA-N

Caramiphen is an anticholinergic drug used in the treatment of Parkinson's disease. In combination with phenylpropanolamine it is used as a cough suppressant and nasal decongestant to treat symptoms associated with respiratory illnesses such as cold, allergies, hay fever, and sinusitis. It was added to the British National Formulary in 1963, with a dosage of 10 to 20 mg. Side effects include nausea, dizziness, and drowsiness.

It binds to the sigma-1 receptor with an IC50 value of 25 nM.

Synthesis

Pattents:

The halogenation of 1-Phenylcyclopentanecarboxylic Acid [77-55-4] (1) gives 1-phenylcyclopentanecarbonyl chloride [17380-62-0] (2). Ester formation with diethylaminoethanol [100-37-8] (3) completes the synthesis of Caramiphen (4).




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