Chlorhexadol

Identification

Name
Chlorhexadol
Accession Number
DB01534
Type
Small Molecule
Groups
Experimental, Illicit
Description

Chlorhexadol is a sedative and hypnotic which is regulated in the United States as a Schedule III controlled substance. It is a derivative of chloral hydrate.

Structure
Thumb
Synonyms
  • 2-methyl-4-(2,2,2-trichloro-1-hydroxy-ethoxy)pentan-2-ol
  • 2-Methyl-4-(2,2,2-trichloro-1-hydroxyethoxy)-2-pentanol
  • 2-methyl-4-(2,2,2-trichloro-1-hydroxyethoxy)pentan-2-ol
  • 2-Pentanol
  • Cloralodol
  • Lora
  • Mecoral
  • Medodorm
  • Merchloral
Categories
Not Available
UNII
W8RD4N93R2
CAS number
3563-58-4
Weight
Average: 265.562
Monoisotopic: 264.008677467
Chemical Formula
C8H15Cl3O3
InChI Key
QVFWZNCVPCJQOP-UHFFFAOYSA-N
InChI
InChI=1S/C8H15Cl3O3/c1-5(4-7(2,3)13)14-6(12)8(9,10)11/h5-6,12-13H,4H2,1-3H3
IUPAC Name
2-methyl-4-(2,2,2-trichloro-1-hydroxyethoxy)pentan-2-ol
SMILES
CC(CC(C)(C)O)OC(O)C(Cl)(Cl)Cl

Pharmacology

Indication
Not Available
Pharmacodynamics

Chloral hydrate has sedative/hypnotic activity which has been shown to extend the sleep of normal made adults via a dose-response relationship. [1]

Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. CONDOURIS GA, BONNYCASTLE DD: A pharmacological investigation of the hypnotic action of a new derivative of chloral hydrate, chlorhexadol. Am J Med Sci. 1961 Nov;242:574-8. [PubMed:13880824]
External Links
KEGG Drug
D07325
PubChem Compound
19094
PubChem Substance
46508125
ChemSpider
18027
ChEBI
135097
ChEMBL
CHEMBL2104116
Wikipedia
Chloralodol

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)103 °CPhysProp
boiling point (°C)304.7°Cat760mmHgNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.24 mg/mLALOGPS
logP2.34ALOGPS
logP1.82ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)9.67ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity58.63 m3·mol-1ChemAxon
Polarizability24.4 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9867
Blood Brain Barrier+0.9769
Caco-2 permeable-0.5191
P-glycoprotein substrateNon-substrate0.6485
P-glycoprotein inhibitor INon-inhibitor0.8956
P-glycoprotein inhibitor IINon-inhibitor0.8033
Renal organic cation transporterNon-inhibitor0.956
CYP450 2C9 substrateNon-substrate0.8184
CYP450 2D6 substrateNon-substrate0.8683
CYP450 3A4 substrateSubstrate0.5052
CYP450 1A2 substrateNon-inhibitor0.9172
CYP450 2C9 inhibitorNon-inhibitor0.8425
CYP450 2D6 inhibitorNon-inhibitor0.9166
CYP450 2C19 inhibitorNon-inhibitor0.5114
CYP450 3A4 inhibitorNon-inhibitor0.8803
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7975
Ames testNon AMES toxic0.7245
CarcinogenicityCarcinogens 0.6919
BiodegradationNot ready biodegradable0.9906
Rat acute toxicity2.7114 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9798
hERG inhibition (predictor II)Non-inhibitor0.9061
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as tertiary alcohols. These are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Alcohols and polyols
Direct Parent
Tertiary alcohols
Alternative Parents
Hemiacetals / Chlorohydrins / Organochlorides / Hydrocarbon derivatives / Alkyl chlorides
Substituents
Tertiary alcohol / Hemiacetal / Halohydrin / Chlorohydrin / Hydrocarbon derivative / Organochloride / Organohalogen compound / Alkyl halide / Alkyl chloride / Aliphatic acyclic compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
Not Available

Drug created on July 31, 2007 07:10 / Updated on November 02, 2018 05:02