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Merck
CN

SML0319

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
NACRES:
NA.77
PubChem Substance ID:
329825324
UNSPSC Code:
12352200
MDL number:
MFCD00242608

Key Documents

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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

SMILES string

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

InChI key

MUPNXGNOIBYHSG-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

H2O: ≥5 mg/mL

storage temp.

2-8°C

Quality Level

100

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 a muscarinic acetylcholine receptor antagonist.
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

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000063765
096M4624V
042M4601V

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Ben Avi Weissman et al.
Toxicology and applied pharmacology, 232(2), 351-358 (2008-08-06)
Potent cholinesterase inhibitors (e.g., soman, sarin), induce a wide range of deleterious effects including convulsions, behavioral impairments and ultimately, death. Due to the likelihood of various scenarios of military or terrorist attacks by these and other chemical weapons, research has
[Scientific raisins from 125 years SMW (Swiss Medical Weekly). On Parpanit, a new agents which modifies extrapyramidal motor disorders. 1946].
E Grünthal
Schweizerische medizinische Wochenschrift, 125(41), 1959-1961 (1995-10-14)
Shahaf Katalan et al.
Archives of toxicology, 87(2), 347-360 (2012-10-12)
Sarin, a potent organophosphate cholinesterase inhibitor, induces an array of toxic effects including convulsions. Many antidotal treatments contain anticonvulsants to block seizure activity and the ensuing brain damage. Magnesium sulfate (MGS) is used to suppress eclamptic seizures in pregnant women
T H Figueiredo et al.
British journal of pharmacology, 164(5), 1495-1505 (2011-04-14)
Caramiphen is a muscarinic antagonist with potent anticonvulsant properties. Here, we investigated the efficacy of caramiphen against behavioural seizures and neuropathology induced by the nerve agent soman, and revealed two mechanisms that may underlie the anticonvulsant efficacy of caramiphen. Rats
R L Hudkins et al.
European journal of pharmacology, 231(3), 485-488 (1993-02-16)
Caramiphen, iodocaramiphen and nitrocaramiphen were examined for affinity at the muscarinic M1, M2 and M3 receptor subtypes in radioligand binding assays. Caramiphen binds with high affinity at the M1 site labeled by [3H]pirenzepine in rat cortex (Ki = 1.2 nM)
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Articles

Muscarinic Acetylcholine Receptors

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

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