T3DB: Ethinamate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (2)XML

Targets (2)

Record Information

Version

2.0

Creation Date

2009-07-21 20:28:12 UTC

Update Date

2014-12-24 20:25:54 UTC

Accession Number

T3D2963

Identification

Common Name

Ethinamate

Class

Small Molecule

Description

Ethinamate is a short-acting sedative-hypnotic medication used to treat insomnia. Regular use leads to tolerance, and it is usually not effective for more than 7 days. Structurally, it does not resemble the barbituates, but it shares many effects with this class of drugs; the depressant effects of ethinamate are, however, generally milder than those of most barbiturates.

Compound Type

Amine
Carbamate
Drug
Ester
Ether
Hypnotic and Sedative
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
1-Ethynylcyclohexanol carbamate
Aethinyl-cyclohexyl-carbamat
Ethinamat
Ethinamatum
Ethinamic acid
Ethinimate
Etinamate
Etinamato
USAF EL-42
Valamin
Valmid

Chemical Formula

C₉H₁₃NO₂

Average Molecular Mass

167.205 g/mol

Monoisotopic Mass

167.095 g/mol

CAS Registry Number

126-52-3

IUPAC Name

1-ethynylcyclohexyl carbamate

Traditional Name

ethinamate

SMILES

OC(=N)OC1(CCCCC1)C#C

InChI Identifier

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

InChI Key

InChIKey=GXRZIMHKGDIBEW-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as ynones. These are organic compounds containing the ynone functional group, an alpha,beta unsaturated ketone group with the general structure RC#C-C(=O)R' (R' not H).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Ynones

Alternative Parents

Substituents

Ynone
Carbamic acid ester
Carbonic acid derivative
Acetylide
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

terminal acetylenic compound (CHEBI:4884 )
carbamate ester (CHEBI:4884 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

sedative

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	94-96°C
Boiling Point	120°C at 3.00E+00 mm Hg
Solubility	2500 mg/L (at 25°C)
LogP	1.2

Predicted Properties

Property	Value	Source
Water Solubility	0.11 g/L	ALOGPS
logP	1.09	ALOGPS
logP	1.54	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	15.37	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	52.32 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	44.57 m³·mol⁻¹	ChemAxon
Polarizability	17.73 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-054o-9000000000-115ca538c5db7623cd36	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-004i-0900000000-3530aac44af3672b4ea8	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-054o-9000000000-115ca538c5db7623cd36	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-004i-0900000000-3530aac44af3672b4ea8	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9400000000-b2399bc8d370f3c24953	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-016r-1900000000-eae16bf8bad39a8aa79b	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-4900000000-5017ae578b8cb02cd66d	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ktf-9100000000-cd1eedbdd6d6fcbfa22e	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-006x-9800000000-e408920834450f49d3fe	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006x-9500000000-877c16eefea2f5a15d9b	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9300000000-b9a9228e0ee207499b99	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-2900000000-10552185ed182d4ba1e0	2021-10-11	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9700000000-cd8eef43ebf47b3d3b7b	2021-10-11	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9100000000-9313282cbda800790a68	2021-10-11	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0avl-2900000000-d0731a549bbc943d745e	2021-10-11	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9500000000-35acbd59dd232e271712	2021-10-11	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-ff48c45d4a47d2073ba7	2021-10-11	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0arv-9100000000-713c62aa52e71fc3560a	2014-09-20	View Spectrum

Toxicity Profile

Route of Exposure

Rapidly absorbed following oral administration.

Mechanism of Toxicity

The mechanism of action is not known. However, studies have shown that ethinamate inhibits carbonic anhydrases I and II (J Biol Chem. 1992 Dec 15;267(35):25044-50). This inhibition by ethinamate is not sufficiently strong, however, to implicate carbonic anhydrases I and II in the mechanism of action.

Metabolism

Hepatic. Half Life: 2.5 hours

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Used for the short-term treatment of insomnia, however, it generally has been replaced by other sedative-hypnotic agents.

Minimum Risk Level

Not Available

Health Effects

They cause slurred speech, disorientation and "drunken" behavior. They are physically and psychologically addictive.

Symptoms

Symptoms of overdose include shortness of breath or slow or troubled breathing, slow heartbeat, severe weakness, chronic confusion, slurred speech, and staggering.

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

HMDB ID

PubChem Compound ID

ChEMBL ID

ChemSpider ID

KEGG ID

UniProt ID

Not Available

OMIM ID

ChEBI ID

4884

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Ethinamate

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Ethinamate

References

Synthesis Reference

Junkmann, K. and Pfeiffer, H.; US. Patent 2,816,910; December 17, 1957; assigned to
Schering AG, Germany.

MSDS

Not Available

General References

Drugs.com [Link]

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. Carbonic anhydrase 1

General Function:: Zinc ion binding
Specific Function:: Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
Gene Name:: CA1
Uniprot ID:: P00915
Molecular Weight:: 28870.0 Da

References

Parr JS, Khalifah RG: Inhibition of carbonic anhydrases I and II by N-unsubstituted carbamate esters. J Biol Chem. 1992 Dec 15;267(35):25044-50. [1460006 ]

Target Details

2. Carbonic anhydrase 2

General Function:: Zinc ion binding
Specific Function:: Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion into the anterior chamber of the eye. Contributes to intracellular pH regulation in the duodenal upper villous epithelium during proton-coupled peptide absorption. Stimulates the chloride-bicarbonate exchange activity of SLC26A6.
Gene Name:: CA2
Uniprot ID:: P00918
Molecular Weight:: 29245.895 Da

References

Parr JS, Khalifah RG: Inhibition of carbonic anhydrases I and II by N-unsubstituted carbamate esters. J Biol Chem. 1992 Dec 15;267(35):25044-50. [1460006 ]

Ethinamate (T3D2963)

Structure for T3D2963: Ethinamate

Targets

References

References