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Details

Stereochemistry ACHIRAL
Molecular Formula C9H13NO2
Molecular Weight 167.205
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETHINAMATE

SMILES

NC(=O)OC1(CCCCC1)C#C

InChI

InChIKey=GXRZIMHKGDIBEW-UHFFFAOYSA-N
InChI=1S/C9H13NO2/c1-2-9(12-8(10)11)6-4-3-5-7-9/h1H,3-7H2,(H2,10,11)

HIDE SMILES / InChI
Ethinamate was used to treat insomnia (trouble in sleeping) under the brand name VALMID, but then was replaced by other more efficacy medicines. The mechanism of action was not known. However, was studies, which showed that ethinamate inhibits carbonic anhydrases I and did not inhibit II. Nevertheless, even inhibition carbonic anhydrases I is not sufficiently strong to implicate carbonic anhydrases I in the mechanism of action.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P00915
Gene ID: 759.0
Gene Symbol: CA1
Target Organism: Homo sapiens (Human)
2.9 mM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
valmid

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
5.9 μg/mL
1 g single, oral
dose: 1 g
route of administration: Oral
experiment type: SINGLE
co-administered:
ETHINAMATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.3 h
1 g single, oral
dose: 1 g
route of administration: Oral
experiment type: SINGLE
co-administered:
ETHINAMATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
Doses

Doses

DosePopulationAdverse events​
15 g single, oral
Overdose
Dose: 15 g
Route: oral
Route: single
Dose: 15 g
Sources:
healthy, 24 years
Health Status: healthy
Age Group: 24 years
Sex: M
Sources:
Other AEs: Breathing slowed...
Other AEs:
Breathing slowed (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Breathing slowed 1 patient
15 g single, oral
Overdose
Dose: 15 g
Route: oral
Route: single
Dose: 15 g
Sources:
healthy, 24 years
Health Status: healthy
Age Group: 24 years
Sex: M
Sources:
PubMed

PubMed

TitleDatePubMed
Reductive metabolism of an alpha,beta-ketoalkyne, 4-phenyl-3-butyn-2-one, by rat liver preparations.
2002 Apr
Patents

Sample Use Guides

In Vivo Use Guide
single oral dose of 1 gram
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
ETHINAMATE
HSDB   INN   JAN   MART.   MI   ORANGE BOOK   VANDF   WHO-DD  
INN  
Official Name English
VALMID
Preferred Name English
ETHINAMATE [VANDF]
Common Name English
CYCLOHEXANOL, 1-ETHYNYL-, CARBAMATE
Systematic Name English
ETHINAMATE [HSDB]
Common Name English
NSC-11538
Code English
ethinamate [INN]
Common Name English
ETHINAMATE [MART.]
Common Name English
ETHINAMATE [MI]
Common Name English
ETHINAMATE [ORANGE BOOK]
Common Name English
ETHINAMATE [JAN]
Common Name English
Ethinamate [WHO-DD]
Common Name English
1-Ethynylcyclohexanol carbamate
Systematic Name English
Classification Tree Code System Code
DEA NO. 2545
Created by admin on Mon Mar 31 18:47:58 GMT 2025 , Edited by admin on Mon Mar 31 18:47:58 GMT 2025
NCI_THESAURUS C29756
Created by admin on Mon Mar 31 18:47:58 GMT 2025 , Edited by admin on Mon Mar 31 18:47:58 GMT 2025
Code System Code Type Description
MESH
C100198
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PRIMARY
SMS_ID
100000082617
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PRIMARY
INN
549
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PRIMARY
NCI_THESAURUS
C65559
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PRIMARY
CAS
126-52-3
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PRIMARY
RXCUI
24474
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PRIMARY RxNorm
IUPHAR
7325
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PRIMARY
ChEMBL
CHEMBL1576
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PRIMARY
EVMPD
SUB07276MIG
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PRIMARY
WIKIPEDIA
ETHINAMATE
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PRIMARY
PUBCHEM
3284
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PRIMARY
NSC
11538
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PRIMARY
DRUG BANK
DB01031
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PRIMARY
CHEBI
4884
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PRIMARY
ECHA (EC/EINECS)
204-789-4
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PRIMARY
DRUG CENTRAL
1081
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PRIMARY
MERCK INDEX
m1137
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PRIMARY Merck Index
HSDB
3325
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PRIMARY
FDA UNII
IAN371PP48
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PRIMARY
EPA CompTox
DTXSID7023013
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PRIMARY