ETHCHLORVYNOL

First approved in 1955

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 Search

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

Molecular Formula	C7H9ClO
Molecular Weight	144.599
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	1
Optical Activity	( + / - )

Description
Sources: https://www.drugs.com/cons/ethchlorvynol.html
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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; anion channel 202 Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1585214 \| https://www.drugbank.ca/drugs/DB00189	Positive Allosteric Modulator 179

Conditions

Condition	Modality	Targets	Highest Phase	Product
Insomnia 108 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1585214	Primary		Approved 8429	PLACIDYL Approved Use Ethchlorvynol is used to treat insomnia (trouble in sleeping). Launch Date 1961

T_1/2

Value	Dose	Co-administered	Analyte	Population
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

Dose	Population	Adverse 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

AE	Significance	Dose	Population
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

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
Toxic amblyopia and peripheral neuropathy with ethchlorvynol abuse.	1969 Dec	5352221
Chiasmal optic neuritis.	1982 Jun	6226702

Patents

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:20:57 GMT 2023` Edited by `admin` on `Fri Dec 15 17:20:57 GMT 2023`
Record UNII	6EIM3851UZ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ETHCHLORVYNOL

Official Name

English

ETHCHLORVYNOL CIV

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