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Details

Stereochemistry RACEMIC
Molecular Formula C7H9ClO
Molecular Weight 144.599
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ETHCHLORVYNOL

SMILES

CCC(O)(\C=C\Cl)C#C

InChI

InChIKey=ZEHYJZXQEQOSON-AATRIKPKSA-N
InChI=1S/C7H9ClO/c1-3-7(9,4-2)5-6-8/h1,5-6,9H,4H2,2H3/b6-5+

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including: http://www.wikidoc.org/index.php/Ethchlorvynol

Ethchlorvynol is used to treat insomnia (trouble in sleeping). It developed by Pfizer in the 1950s. In the United States it was sold by Abbott Laboratories under the tradename Placidyl. Although the exact mechanism of action is unknown, ethchlorvynol appears to depress the central nervous system in a manner similar to that of barbiturates – by means of GABA-A receptors modulation. Moderate side effects are: Skin rash or hives; dizziness or faintness; unusual excitement, nervousness, or restlessness. It is addictive and after prolonged use can cause withdrawal symptoms including convulsions, hallucinations, and memory loss.

CNS Activity

Originator

McLamore, W.M.|P'an, S.Y.|Bavley, A.
1
Sources: DOI: 10.1021/jo01119a018

Approval Year

1955
116
Targets

Targets

Primary TargetPharmacologyConditionPotency
Positive Allosteric Modulator
179
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
PLACIDYL

Approved Use

Ethchlorvynol is used to treat insomnia (trouble in sleeping).

Launch Date

-2.72851206E11
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
25 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3822854
unknown, oral
 ETHCHLORVYNOL serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
15 g single, oral
Overdose
Dose: 15 g
Route: oral
Route: single
Dose: 15 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/484952
healthy, 16 years
n = 1
Health Status: healthy
Age Group: 16 years
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/484952
Other AEs: Pneumonia...
Other AEs:
Pneumonia (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/484952
12 g single, oral
Overdose
Dose: 12 g
Route: oral
Route: single
Dose: 12 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/484952
healthy, 17 years
n = 1
Health Status: healthy
Age Group: 17 years
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/484952
Other AEs: Anemia, Hypocalcemia...
Other AEs:
Anemia (1 patient)
Hypocalcemia (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/484952
500 mg 1 times / day multiple, oral
Dose: 500 mg, 1 times / day
Route: oral
Route: multiple
Dose: 500 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/417376
unhealthy, 21-28 years
n = 4
Health Status: unhealthy
Condition: insomnia
Age Group: 21-28 years
Sex: M+F
Population Size: 4
Sources:
https://pubmed.ncbi.nlm.nih.gov/417376
Other AEs: Headache, Headache...
Other AEs:
Headache (severe, 1 patient)
Headache (severe, 1 patient)
Stuttering (1 patient)
Confusion (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/417376
40 mg/kg single, intravenous
Overdose
Dose: 40 mg/kg
Route: intravenous
Route: single
Dose: 40 mg/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/942681
healthy, 22-23 years2
n = 2
Health Status: healthy
Age Group: 22-23 years2
Sex: F
Population Size: 2
Sources:
https://pubmed.ncbi.nlm.nih.gov/942681
Other AEs: Pulmonary edema...
Other AEs:
Pulmonary edema (2 patients)
Sources:
https://pubmed.ncbi.nlm.nih.gov/942681
22 g single, oral
Overdose
Dose: 22 g
Route: oral
Route: single
Dose: 22 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/484952
healthy, 51 years
n = 1
Health Status: healthy
Age Group: 51 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/484952
Other AEs: Pancreatitis, Pneumonia...
Other AEs:
Pancreatitis (1 patient)
Pneumonia (1 patient)
Pancreatitis (acute, 1 patient)
Anemia (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/484952
500 mg 1 times / day multiple, oral
Dose: 500 mg, 1 times / day
Route: oral
Route: multiple
Dose: 500 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/13927359
unhealthy
n = 2
Health Status: unhealthy
Condition: alcoholics
Sex: M+F
Population Size: 2
Sources:
https://pubmed.ncbi.nlm.nih.gov/13927359
Disc. AE: Unconsciousness...
AEs leading to
discontinuation/dose reduction:
Unconsciousness (2 patients)
Sources:
https://pubmed.ncbi.nlm.nih.gov/13927359
AEs

AEs

AESignificanceDosePopulation
Pneumonia 1 patient
15 g single, oral
Overdose
Dose: 15 g
Route: oral
Route: single
Dose: 15 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/484952
healthy, 16 years
n = 1
Health Status: healthy
Age Group: 16 years
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/484952
Anemia 1 patient
12 g single, oral
Overdose
Dose: 12 g
Route: oral
Route: single
Dose: 12 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/484952
healthy, 17 years
n = 1
Health Status: healthy
Age Group: 17 years
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/484952
Hypocalcemia 1 patient
12 g single, oral
Overdose
Dose: 12 g
Route: oral
Route: single
Dose: 12 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/484952
healthy, 17 years
n = 1
Health Status: healthy
Age Group: 17 years
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/484952
Confusion 1 patient
500 mg 1 times / day multiple, oral
Dose: 500 mg, 1 times / day
Route: oral
Route: multiple
Dose: 500 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/417376
unhealthy, 21-28 years
n = 4
Health Status: unhealthy
Condition: insomnia
Age Group: 21-28 years
Sex: M+F
Population Size: 4
Sources:
https://pubmed.ncbi.nlm.nih.gov/417376
Stuttering 1 patient
500 mg 1 times / day multiple, oral
Dose: 500 mg, 1 times / day
Route: oral
Route: multiple
Dose: 500 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/417376
unhealthy, 21-28 years
n = 4
Health Status: unhealthy
Condition: insomnia
Age Group: 21-28 years
Sex: M+F
Population Size: 4
Sources:
https://pubmed.ncbi.nlm.nih.gov/417376
Headache severe, 1 patient
500 mg 1 times / day multiple, oral
Dose: 500 mg, 1 times / day
Route: oral
Route: multiple
Dose: 500 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/417376
unhealthy, 21-28 years
n = 4
Health Status: unhealthy
Condition: insomnia
Age Group: 21-28 years
Sex: M+F
Population Size: 4
Sources:
https://pubmed.ncbi.nlm.nih.gov/417376
Headache severe, 1 patient
500 mg 1 times / day multiple, oral
Dose: 500 mg, 1 times / day
Route: oral
Route: multiple
Dose: 500 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/417376
unhealthy, 21-28 years
n = 4
Health Status: unhealthy
Condition: insomnia
Age Group: 21-28 years
Sex: M+F
Population Size: 4
Sources:
https://pubmed.ncbi.nlm.nih.gov/417376
Pulmonary edema 2 patients
40 mg/kg single, intravenous
Overdose
Dose: 40 mg/kg
Route: intravenous
Route: single
Dose: 40 mg/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/942681
healthy, 22-23 years2
n = 2
Health Status: healthy
Age Group: 22-23 years2
Sex: F
Population Size: 2
Sources:
https://pubmed.ncbi.nlm.nih.gov/942681
Anemia 1 patient
22 g single, oral
Overdose
Dose: 22 g
Route: oral
Route: single
Dose: 22 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/484952
healthy, 51 years
n = 1
Health Status: healthy
Age Group: 51 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/484952
Pancreatitis 1 patient
22 g single, oral
Overdose
Dose: 22 g
Route: oral
Route: single
Dose: 22 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/484952
healthy, 51 years
n = 1
Health Status: healthy
Age Group: 51 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/484952
Pneumonia 1 patient
22 g single, oral
Overdose
Dose: 22 g
Route: oral
Route: single
Dose: 22 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/484952
healthy, 51 years
n = 1
Health Status: healthy
Age Group: 51 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/484952
Pancreatitis acute, 1 patient
22 g single, oral
Overdose
Dose: 22 g
Route: oral
Route: single
Dose: 22 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/484952
healthy, 51 years
n = 1
Health Status: healthy
Age Group: 51 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/484952
Unconsciousness 2 patients
Disc. AE
500 mg 1 times / day multiple, oral
Dose: 500 mg, 1 times / day
Route: oral
Route: multiple
Dose: 500 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/13927359
unhealthy
n = 2
Health Status: unhealthy
Condition: alcoholics
Sex: M+F
Population Size: 2
Sources:
https://pubmed.ncbi.nlm.nih.gov/13927359
Sourcing

Sourcing

Vendor/AggregatorIDURL
AAA Chemistry
AR-1I7766
ABI Chem
AC1NQXZT
ABI Chem
AC1Q3HC3
AK Scientific, Inc. (AKSCI)
X2131
http://www.aksci.com/item_detail.php?cat=X2131
AN PharmaTech
AN-22729
Ambinter
Amb13889603
http://www.ambinter.com/reference/13889603
Ambinter
Amb22055189
http://www.ambinter.com/reference/22055189
ChemMol
49415507
http://www.chemmol.com/chemmol/49415507.html
Compound Cloud
5281077
Enamine
BBV-75779258
Enamine
BBV-82679473
Enamine
BBV-95538700
NovoSeek
5281077
Smolecule
S527512
http://www.smolecule.com/products/s527512
THE BioTek
bt-267819
https://www.thebiotek.com/product/inhibitors/bt-267819
Toronto Research Chemicals
KIT4585
ZINC
ZINC000000000267
http://zinc15.docking.org/substances/ZINC000000000267
ZINC
ZINC000000897283
http://zinc15.docking.org/substances/ZINC000000897283
ZINC
ZINC000012503063
http://zinc15.docking.org/substances/ZINC000012503063
ZINC
ZINC000012503065
http://zinc15.docking.org/substances/ZINC000012503065
eMolecules
262671243
mcule
MCULE-4520269519
PubMed

PubMed

TitleDatePubMed
Toxic amblyopia and peripheral neuropathy with ethchlorvynol abuse.
1969 Dec
Seven cases of somnambulism induced by drugs.
1979 Jul
Psychosis with withdrawal from ethchlorvynol.
1980 Feb
Chiasmal optic neuritis.
1982 Jun
Acute urinary retention precipitated by ethchlorvynol overdose.
1986 Sep
Patents

Patents

US 2746900
1

Sample Use Guides

In Vivo Use Guide
500 to 1000 mg at bedtime
Route of Administration: Oral
In Vitro Use Guide
Monolayers of endothelial cells exposed to 1mg/ml of Ethchlorvynol for 30 min and then fixed and stained with Eosin-Coomassie blue demonstrated moderate cell retraction with distinct gaps between adjacent endothelial cells.
Name Type Language
ETHCHLORVYNOL
HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USP   VANDF   WHO-DD  
INN  
Official Name English
ETHCHLORVYNOL CIV
USP-RS  
Common Name English
SERENSIL
Brand Name English
ETHYL .BETA.-CHLOROVINYL ETHYNYL CARBINOL
Systematic Name English
ETHCHLORVYNOL [MART.]
Common Name English
ROERIDORM
Brand Name English
ethchlorvynol [INN]
Common Name English
1-PENTEN-4-YN-3-OL, 1-CHLORO-3-ETHYL-, (1E)-
Systematic Name English
ALVINOL
Brand Name English
ETHCHLORVYNOL [HSDB]
Common Name English
3-(.BETA.-CHLORVINYL)-1-PENTYN-3-OL
Common Name English
1-Chloro-3-ethyl-1-penten-4-yn-3-ol
Systematic Name English
NOSTEL
Brand Name English
ETHCHLORVYNOL [USP MONOGRAPH]
Common Name English
ETHCHLORVYNOL [VANDF]
Common Name English
PLACIDYL
Brand Name English
NORMOSON
Brand Name English
ETHCHLORVYNOL CIV [USP-RS]
Common Name English
ARVYNOL
Brand Name English
ETHCHLORVYNOL [JAN]
Common Name English
NSC-30372
Code English
Ethchlorvynol [WHO-DD]
Common Name English
SERENESIL
Brand Name English
1-PENTEN-4-YN-3-OL, 1-CHLORO-3-ETHYL-
Systematic Name English
ETHCHLORVYNOL [MI]
Common Name English
ETHCHLORVYNOL [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
WHO-ATC N05CM08
Created by admin on Fri Dec 15 17:20:57 UTC 2023 , Edited by admin on Fri Dec 15 17:20:57 UTC 2023
DEA NO. 2540
Created by admin on Fri Dec 15 17:20:57 UTC 2023 , Edited by admin on Fri Dec 15 17:20:57 UTC 2023
WHO-VATC QN05CM08
Created by admin on Fri Dec 15 17:20:57 UTC 2023 , Edited by admin on Fri Dec 15 17:20:57 UTC 2023
NCI_THESAURUS C29756
Created by admin on Fri Dec 15 17:20:57 UTC 2023 , Edited by admin on Fri Dec 15 17:20:57 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C61758
Created by admin on Fri Dec 15 17:20:57 UTC 2023 , Edited by admin on Fri Dec 15 17:20:57 UTC 2023
PRIMARY
EPA CompTox
DTXSID2023010
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PRIMARY
MERCK INDEX
m5054
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PRIMARY Merck Index
HSDB
3079
Created by admin on Fri Dec 15 17:20:57 UTC 2023 , Edited by admin on Fri Dec 15 17:20:57 UTC 2023
PRIMARY
CHEBI
4882
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PRIMARY
CAS
1135334-09-6
Created by admin on Fri Dec 15 17:20:57 UTC 2023 , Edited by admin on Fri Dec 15 17:20:57 UTC 2023
ALTERNATIVE
NSC
30372
Created by admin on Fri Dec 15 17:20:57 UTC 2023 , Edited by admin on Fri Dec 15 17:20:57 UTC 2023
PRIMARY
PUBCHEM
5281077
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PRIMARY
RXCUI
4118
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PRIMARY RxNorm
CAS
113-18-8
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PRIMARY
CAS
8060-77-3
Created by admin on Fri Dec 15 17:20:57 UTC 2023 , Edited by admin on Fri Dec 15 17:20:57 UTC 2023
SUPERSEDED
EVMPD
SUB07273MIG
Created by admin on Fri Dec 15 17:20:57 UTC 2023 , Edited by admin on Fri Dec 15 17:20:57 UTC 2023
PRIMARY
DRUG BANK
DB00189
Created by admin on Fri Dec 15 17:20:57 UTC 2023 , Edited by admin on Fri Dec 15 17:20:57 UTC 2023
PRIMARY
SMS_ID
100000082596
Created by admin on Fri Dec 15 17:20:57 UTC 2023 , Edited by admin on Fri Dec 15 17:20:57 UTC 2023
PRIMARY
INN
532
Created by admin on Fri Dec 15 17:20:57 UTC 2023 , Edited by admin on Fri Dec 15 17:20:57 UTC 2023
PRIMARY
FDA UNII
6EIM3851UZ
Created by admin on Fri Dec 15 17:20:57 UTC 2023 , Edited by admin on Fri Dec 15 17:20:57 UTC 2023
PRIMARY
CAS
5406-29-1
Created by admin on Fri Dec 15 17:20:57 UTC 2023 , Edited by admin on Fri Dec 15 17:20:57 UTC 2023
SUPERSEDED
ChEMBL
CHEMBL591
Created by admin on Fri Dec 15 17:20:57 UTC 2023 , Edited by admin on Fri Dec 15 17:20:57 UTC 2023
PRIMARY
MESH
D004984
Created by admin on Fri Dec 15 17:20:57 UTC 2023 , Edited by admin on Fri Dec 15 17:20:57 UTC 2023
PRIMARY
RS_ITEM_NUM
1258305
Created by admin on Fri Dec 15 17:20:57 UTC 2023 , Edited by admin on Fri Dec 15 17:20:57 UTC 2023
PRIMARY
WIKIPEDIA
ETHCHLORVYNOL
Created by admin on Fri Dec 15 17:20:57 UTC 2023 , Edited by admin on Fri Dec 15 17:20:57 UTC 2023
PRIMARY
IUPHAR
7180
Created by admin on Fri Dec 15 17:20:57 UTC 2023 , Edited by admin on Fri Dec 15 17:20:57 UTC 2023
PRIMARY
DRUG CENTRAL
1078
Created by admin on Fri Dec 15 17:20:57 UTC 2023 , Edited by admin on Fri Dec 15 17:20:57 UTC 2023
PRIMARY
ACTIVE MOIETY
Structure of ETHCHLORVYNOL
NIH
NCATS
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HHS VULNERABILITY DISCLOSURE
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