(1E)-1-chloro-3-ethylpent-1-en-4-yn-3-ol

• ChemBase ID: 74
• Molecular Formular: C7H9ClO
• Molecular Mass: 144.59876
• Monoisotopic Mass: 144.03419259
• SMILES: Cl/C=C/C(O)(CC)C#C
• Canonical SMILES: CCC(C#C)(/C=C/Cl)O
• InChI: InChI=1S/C7H9ClO/c1-3-7(9,4-2)5-6-8/h1,5-6,9H,4H2,2H3/b6-5+
• InChIKey: ZEHYJZXQEQOSON-AATRIKPKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1E)-1-chloro-3-ethylpent-1-en-4-yn-3-ol; 1-chloro-3-ethylpent-1-en-4-yn-3-ol
• IUPAC Traditional name: ethchlorvynol; 1-chloro-3-ethylpent-1-en-4-yn-3-ol
• Brand Name: Alvinol; Arvynol; Normonson; Normosan; Normoson; Nostel; Nromoson; Placidil; Placidyl; Roeridorm; Serenesil; Serenil; Serensil; Serensiloline
• Synonyms: 1-Chloro-3-ethyl-1-penten-4-yn-3-ol; 3-(β-Chlorvinyl)-1-pentyn-3-ol; Alvinol; Arvynol; Ethchlorvynol; Ethyl β-Chlorovinyl Ethynyl Carbinol; NSC 30372; Normoson; Nostel; Placidyl; Roeridorm; Serenesil; Serensil; Aethyl-chlorvynol; Ethochlorvynol; Ethychlorvynol; Ethclorvynol; Ethchlorvinyl; Ethchlorvinol; Ethchlorovynol; Etchlorvinolo; Ethchlorvynol

Database IDs

• CAS Number: 113-18-8
• PubChem SID: 160963537
• PubChem CID: 5281077
• ATC CODE: N05CM08
• CHEMBL: 591
• Chemspider ID: 4444534
• DrugBank ID: DB00189
• KEGG ID: D00704
• Unique Ingredient Identifier: 6EIM3851UZ
• Wikipedia Title: Ethchlorvynol

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.877911
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 1.6208194
• LogD (pH = 7.4): 1.620818
• Log P: 1.6208194
• Molar Refractivity: 38.6382 cm^3
• Polarizability: 14.74078 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.45
• LOG S: -3.0
• Solubility (Water): 1.43e-01 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Clear Colorless Oil
• Hydrophobicity(logP): 1.8

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer

Pharmacology Properties

• Admin Routes: Oral
• Protein Bound: 35–50%
• Legal Status: Schedule IV

DETAILS

DrugBank - DB00189

• Drug Groups: illicit; approved
• Description: Ethchlorvynol is a sedative and hypnotic drug. It has been used to treat insomnia, but has been largely superseded and is only offered where an intolerance or allergy to other drugs exists. [Wikipedia]
• Indication: Used for short-term hypnotic therapy in the management of insomnia for periods of up to one week in duration; however, this medication generally has been replaced by other sedative-hypnotic agents.
• Pharmacology: Ethchlorvynol is a sedative drug and schedule IV (USA) controlled substance. It produces cerebral depression, however the exact mechanism of action is not known.
• Toxicity: Symptoms of overdose include thrombocytopenia.
• Affected Organisms: Humans and other mammals
• Biotransformation: About 90% of a dose is metabolized in the liver. Some ethchlorvynol may also be metabolized in the kidneys. Ethchlorvynol and metabolites undergo extensive enterohepatic recirculation.
• Absorption: Rapidly absorbed from gastrointestinal tract.
• Half Life: Plasma half-life is approximately 10 to 20 hours, terminal half-life is 21-100 hours.
• Protein Binding: 35-50%
• External Links: Wikipedia; Drugs.com

Toronto Research Chemicals - E677000

Controlled substance (depressant). Sedative; hypnotic.

REFERENCES

• Horwitz, et al.: Drug Metab. Dispos., 8, 77 (1980)