Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

SML0319

Sigma-Aldrich

Caramiphen hydrochloride

≥98% (HPLC)

Synonym(s):

2-(Diethylamino)ethyl 1-phenylcyclopentane-1-carboxylate hydrochloride, Caramiphenium chloride salt, G 2747, Panparnit, Parpanil, Parpanit, Pentaphen, Pentaphene hydrochloride

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C18H27NO2 · HCl
CAS Number:
125-85-9
Molecular Weight:
325.87
MDL number:
MFCD00242608
UNSPSC Code:
12352200
PubChem Substance ID:
329825324
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

H2O: ≥5 mg/mL

storage temp.

2-8°C

SMILES string

Cl.CCN(CC)CCOC(=O)C1(CCCC1)c2ccccc2

InChI

1S/C18H27NO2.ClH/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;1H

InChI key

MUPNXGNOIBYHSG-UHFFFAOYSA-N

Application

Caramiphen hydrochloride has been used to test its inhibitory effect on voltage-gated Na+ currents using the patch-clamp method.

Biochem/physiol Actions

Caramiphen hydrochloride is non-narcotic and possesses many biological functionalities of being antitussive, anticonvulsive, and neuroprotective. It induces sensory block and displays less toxicity when compared to bupivacaine. The local anesthetic functionality of caramiphen is mediated by its inhibitory effect on voltage-gated Na+ currents.
Caramiphen is an anti-muscarinic similar to atropine; muscarinic acetylcholine receptor antagonist. Caramiphen is commonly used as a cough suppresant, but is also administered for the treatment of Parkinson′s disease. The compound has also been shown to have anti-depressant properties that may involve inhibition of G protein-coupled inwardly rectifying potassium channel GIRK.

Features and Benefits

This compound is featured on the Acetylcholine Receptors (Muscarinic) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Trond Myhrer et al.
Neurotoxicology, 32(6), 923-930 (2011-05-17)
Results from studies based on microinfusions into seizure controlling brain sites (area tempestas, medial septum, perirhinal cortex, posterior piriform cortex) have shown that procyclidine, muscimol, caramiphen, and NBQX, but not ketamine, exert anticonvulsant effects against soman-induced seizures. The purpose of
M K Schultz et al.
Toxicology and applied pharmacology, 259(3), 376-386 (2012-02-09)
Therapy of seizure activity following exposure to the nerve agent soman (GD) includes treatment with the anticonvulsant diazepam (DZP), an allosteric modulator of γ-aminobutyric acid A (GABA(A)) receptors. However, seizure activity itself causes the endocytosis of GABA(A) receptors and diminishes
J I Székely et al.
Pharmacology, biochemistry, and behavior, 47(3), 709-713 (1994-03-01)
Because dextromethorphan (DM) has been shown to inhibit the locomotor stimulant effects of phencyclidine (PCP), this study explored further the possible interaction between drugs acting on DM and PCP receptor sites. Caramiphen, an antitussive that binds with high affinity to
Yu-Wen Chen et al.
Neuroscience letters, 469(1), 174-178 (2009-12-08)
The aims of the study were to evaluate the spinal anesthetic effect of caramiphen and also assess spinal anesthetic interactions of caramiphen with lidocaine. Lidocaine, a common local anesthetic, was used as control. Dose-dependent responses of intrathecal caramiphen on spinal
Ching-Hsia Hung et al.
Regional anesthesia and pain medicine, 37(1), 34-39 (2011-12-14)
Caramiphen produces spinal anesthesia; caramiphen and carbetapentane have never been tested as infiltrative cutaneous analgesic. The aim of this study was to compare cutaneous analgesia of caramiphen and carbetapentane with bupivacaine and evaluated their central nervous system and cardiovascular toxicity.
View All Related Papers

Articles

Muscarinic Acetylcholine Receptors

Muscarinic acetylcholine receptors mediate acetylcholine actions in CNS and non-nervous tissues, crucial for cell signaling.

Muscarinic Acetylcholine Receptors

Muscarinic acetylcholine receptors mediate acetylcholine actions in CNS and non-nervous tissues, crucial for cell signaling.

Muscarinic Acetylcholine Receptors

Muscarinic acetylcholine receptors mediate acetylcholine actions in CNS and non-nervous tissues, crucial for cell signaling.

Muscarinic Acetylcholine Receptors

Muscarinic acetylcholine receptors mediate acetylcholine actions in CNS and non-nervous tissues, crucial for cell signaling.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service