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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

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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’.

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M R Domenici et al.
General pharmacology, 24(4), 991-998 (1993-07-01)
1. The effects of the non-opioid antitussives caramiphen and carbetapentane and of the anticonvulsants 5,5-diphenylhydantoin and MK 801 were tested towards hypoxia-induced electrical changes in rat hippocampal slices. 2. The incidence of appearance of hypoxia-induced epileptiform bursting was significantly decreased
G Diana et al.
Life sciences, 52(19), 1547-1557 (1993-01-01)
The effects of the non-opioid oral antitussives dextromethorphan (DM) and caramiphen (CP) were tested against the behavioural and EEG effects elicited by the N-methyl-D-aspartate (NMDA) antagonists dizocilpine (MK 801) and phencyclidine (PCP) in rats and mice. PCP (1.25-10 mg/kg i.p.)
Trond Myhrer et al.
Neurotoxicology, 34, 128-134 (2012-11-21)
Microinfusion of anticonvulsants into the perirhinal cortex through 1 guide cannula in each hemisphere only invades a small area of this seizure controlling site in rats exposed to soman. The purpose of the present study was to examine whether infusions
Yuk-Man Leung et al.
European journal of pharmacology, 746, 213-220 (2014-12-03)
The underlying mechanisms for the action of caramiphen used in local anesthesia are not well understood. The purpose of this study was to evaluate the block of caramiphen on voltage-gated Na⁺ channels and in spinal anesthesia. We investigated the effect
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.
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Muscarinic Acetylcholine Receptors

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