CARAMIPHEN

First approved in 1949

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H27NO2
Molecular Weight	289.4125
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN(CC)CCOC(=O)C1(CCCC1)C2=CC=CC=C2

InChI

InChIKey=OFAIGZWCDGNZGT-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C18H27NO2
Molecular Weight	289.4125
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25446426 | https://www.ncbi.nlm.nih.gov/pubmed/18110872

Caramiphen is a muscarinic M1 acetylcholine receptor antagonist, which was used for the treatment of Parkinson Disease and cough, but then there using were discontinued. Caramiphen is also used in local anesthesia, and effect could be achieved through the suppression of voltage-gated Na⁺ currents.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
voltage-gated Na⁺ currents 3 Target ID: voltage-gated Na⁺ currents Sources: https://www.ncbi.nlm.nih.gov/pubmed/25446426	Inhibitor 8504		52.1 µM [IC50]
Muscarinic acetylcholine receptor M1 168 Target ID: P11229 Gene ID: 1128.0 Gene Symbol: CHRM1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/8449241	Antagonist 2849		1.2 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cough 106 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3322860	Primary		Approved 8583	SKF TUSS-ORNADE Approved Use Unknown
Parkinson's disease 232 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18110872	Primary		Approved 8583	parpanit Approved Use Unknown

Doses

Dose	Population	Adverse events
20 mg single, oral Dose: 20 mg Route: oral Route: single Dose: 20 mg Sources: https://pubmed.ncbi.nlm.nih.gov/25201353/	healthy, adult Health Status: healthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/25201353/	Other AEs: Nausea, Dizziness... Other AEs: Nausea (3 patients) Dizziness (2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/25201353/

AEs

AE	Significance	Dose	Population
Dizziness	2 patients	20 mg single, oral Dose: 20 mg Route: oral Route: single Dose: 20 mg Sources: https://pubmed.ncbi.nlm.nih.gov/25201353/	healthy, adult Health Status: healthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/25201353/
Nausea	3 patients	20 mg single, oral Dose: 20 mg Route: oral Route: single Dose: 20 mg Sources: https://pubmed.ncbi.nlm.nih.gov/25201353/	healthy, adult Health Status: healthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/25201353/

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY571133	https://www.001chemical.com/chem/77-22-5
Acorn PharmaTech	ACN-057466	http://www.acornpharmatech.com/
Aurora Fine Chemicals LLC	K02.797.422	http://online.aurorafinechemicals.com/info?ID=K02.797.422
ChemMol	99151441	http://www.chemmol.com/chemmol/99151441.html
Chemspace	CSSS00020619634	https://chem-space.com/CSSS00020619634
eNovation Chemicals	D671966	https://www.enovationchem.com/ProductDetails.asp?ProductID=D671966
mcule	MCULE-4063768824	https://mcule.com/MCULE-4063768824/
Molcore	MC571133	https://www.molcore.com/product/77-22-5
Smolecule	S522623	http://www.smolecule.com/products/s522623
THE BioTek	bt-262712	https://www.thebiotek.com/product/inhibitors/bt-262712

PubMed

Title	Date	PubMed
The anticholinergic and antiglutamatergic drug caramiphen reduces seizure duration in soman-exposed rats: synergism with the benzodiazepine diazepam.	2012-03-15	22310180
Identification of neuronal target areas for nerve agents and specification of receptors for pharmacological treatment.	2010-12	20624420
Antidepressant-like effect of centrally acting non-narcotic antitussive caramiphen in a forced swimming test.	2010-09-13	20621160
[Novel antidepressant-like action of drugs possessing GIRK channel blocking action in rats].	2010-05	20460867
Isobolographic analysis of caramiphen and lidocaine on spinal anesthesia in rats.	2010-01-18	19962431
Roles of perirhinal and posterior piriform cortices in control and generation of seizures: a microinfusion study in rats exposed to soman.	2010-01	19833150
Therapy against organophosphate poisoning: the importance of anticholinergic drugs with antiglutamatergic properties.	2008-10-15	18680758
Antiparkinson drugs used as prophylactics for nerve agents: studies of cognitive side effects in rats.	2008-06	18384867
Efficacy of antidotal treatment against sarin poisoning: the superiority of benactyzine and caramiphen.	2008-02-15	18320638
Anticonvulsant efficacy of drugs with cholinergic and/or glutamatergic antagonism microinfused into area tempestas of rats exposed to soman.	2008-02	17710542
Extrapolating from animal studies to the efficacy in humans of a pretreatment combination against organophosphate poisoning.	2007-05	17009047
Anticholinergic and antiglutamatergic agents protect against soman-induced brain damage and cognitive dysfunction.	2003-09	12832655
Caramiphen and scopolamine prevent soman-induced brain damage and cognitive dysfunction.	2002-05	12164550
Anti-nicotinic properties of anticholinergic antiparkinson drugs.	1998-11	9877318

Patents

Sample Use Guides

In Vivo Use Guide

2.5 to 6.0 mg/kg

Route of Administration: Intravenous

In Vitro Use Guide

It was investigated the effect of caramiphen (300uM) on voltage-gated sodium channels in differentiated neuronal NG108-15 cells. Caramiphen exhibited a milder state-dependence of block (IC₅₀ of 52.1 and 99.5 µM at holding potentials of -70 and -100 mV, respectively).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:45:06 GMT 2025` Edited by `admin` on `Mon Mar 31 17:45:06 GMT 2025`
Record UNII	97J7NP0XJY
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CARAMIPHEN

Official Name

English

CARAMIPHEN [MI]

Preferred Name

English

caramiphen [INN]

Common Name

English

Caramiphen [WHO-DD]

Common Name

English

1-PHENYLCYCLOPENTANECARBOXYLIC ACID 2-(DIETHYLAMINO)ETHYL ESTER

Systematic Name

English

CARAMIPHEN [VANDF]

Common Name

English

DIETHYLAMINOETHYL 1-PHENYLCYCLOPENTANE-1-CARBOXYLATE

Systematic Name

English

2-DIETHYLAMINOETHYL 1-PHENYLCYCLOPENTANE-1-CARBOXYLATE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C66917