Caramiphen

Caramiphen is an anticholinergic drug used in the treatment of Parkinson's disease.[1] 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.[2] 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.[3]

Caramiphen
Clinical data
Trade namesCarafen
ATC code
  • None
Identifiers
IUPAC name
  • 2-(Diethylamino)ethyl 1-phenylcyclopentanecarboxylate
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.922
Chemical and physical data
FormulaC18H27NO2
Molar mass289.419 g·mol−1
3D model (JSmol)
SMILES
  • O=C(OCCN(CC)CC)C2(c1ccccc1)CCCC2
InChI
  • 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

It binds to the sigma-1 receptor with an IC50 value of 25 nM.[4]

Synthesis
Pattents:[5][6][7]

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).

References
  1. "Caramiphen". drugs.com. Retrieved 26 September 2012.
  2. "Caramiphen with phenylpropanolamine-oral, Ordrine AT, Rescaps-D, Tuss Vernade, Tusso-Gest". medicine.net. Archived from the original on 29 October 2012. Retrieved 26 September 2012.
  3. BEIRN SF; LAVELLE S (May 2, 1964). "To-day's drugs: Cough suppressants". Br Med J. 1 (5391): 1165–1167. doi:10.1136/bmj.1.5391.1165. PMC 1813498. PMID 14120813.
  4. Klein M, Musacchio JM (October 10, 1988). "Dextromethorphan binding sites in the guinea pig brain". Cellular and Molecular Neurobiology. 8 (2): 149–156. doi:10.1007/BF00711241. PMID 3044591. S2CID 33844132.
  5. Franz Hafliger, Henry Martin, U.S. Patent 2,404,588 (1946 to Geigy Ag J R).
  6. Anon., CH 234452 (1944 to Geigy Ag J R).
  7. Japan. Pat., 52 78, (1952); CA, 48, 8820e



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