Chlorphentermine

Identification

Name
Chlorphentermine
Accession Number
DB01556
Type
Small Molecule
Groups
Illicit, Withdrawn
Description

A sympathomimetic agent that was formerly used as an anorectic. It has properties similar to those of dextroamphetamine. It has been implicated in lipid storage disorders and pulmonary hypertension. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1223)

Structure
Thumb
Synonyms
  • 4-Chloro-a,a-dimethylbenzeneethanamine
  • 4-Chloro-a,a-dimethylphenethylamine
  • a,a-Dimethyl-p-chlorophenethylamine
  • Chlorphenterminum
  • Clorfentermina
Product Ingredients
IngredientUNIICASInChI Key
Chlorphentermine hydrochlorideRL11HOJ7DM151-06-4WEJDYJKJPUPMLH-UHFFFAOYSA-N
International/Other Brands
Apsedon / Desopimon / Lucofen
Categories
UNII
NHW07912O7
CAS number
461-78-9
Weight
Average: 183.678
Monoisotopic: 183.08147716
Chemical Formula
C10H14ClN
InChI Key
ZCKAMNXUHHNZLN-UHFFFAOYSA-N
InChI
InChI=1S/C10H14ClN/c1-10(2,12)7-8-3-5-9(11)6-4-8/h3-6H,7,12H2,1-2H3
IUPAC Name
1-(4-chlorophenyl)-2-methylpropan-2-amine
SMILES
CC(C)(N)CC1=CC=C(Cl)C=C1

Pharmacology

Indication

Used as an appetite suppressant.

Pharmacodynamics

Chlorphentermine is a relatively weak stimulant with little abuse potential. It is no longer used due mainly to safety concerns, as it has a serotonergic effects profile similar to other withdrawn appetite suppressants such as fenfluramine and aminorex which were found to cause pulmonary hypertension and cardiac fibrosis following prolonged use.

Mechanism of action
Not Available
Absorption

Well absorbed following oral administration.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life

40 hours

Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of serotonin syndrome can be increased when 2,5-Dimethoxy-4-ethylamphetamine is combined with Chlorphentermine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of serotonin syndrome can be increased when Chlorphentermine is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3-isobutyl-1-methyl-7H-xanthineThe risk or severity of adverse effects can be increased when Chlorphentermine is combined with 3-isobutyl-1-methyl-7H-xanthine.
3,4-MethylenedioxyamphetamineThe risk or severity of serotonin syndrome can be increased when 3,4-Methylenedioxyamphetamine is combined with Chlorphentermine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of serotonin syndrome can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Chlorphentermine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of serotonin syndrome can be increased when Chlorphentermine is combined with 5-methoxy-N,N-dimethyltryptamine.
6-O-benzylguanineThe risk or severity of adverse effects can be increased when Chlorphentermine is combined with 6-O-benzylguanine.
7-DeazaguanineThe risk or severity of adverse effects can be increased when Chlorphentermine is combined with 7-Deazaguanine.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of serotonin syndrome can be increased when Chlorphentermine is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.
7,9-DimethylguanineThe risk or severity of adverse effects can be increased when Chlorphentermine is combined with 7,9-Dimethylguanine.
Food Interactions
Not Available

References

General References
  1. GYLYS JA, HART JJ, WARREN MR: Chlorphentermine, a new anorectic agent. J Pharmacol Exp Ther. 1962 Sep;137:365-73. [PubMed:13903304]
External Links
KEGG Compound
C07559
PubChem Compound
10007
PubChem Substance
46505599
ChemSpider
9613
BindingDB
85704
ChEBI
3646
ChEMBL
CHEMBL1201269
Wikipedia
Chlorphentermine

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
boiling point (°C)100-102 °C at 2.00E+00 mm HgNot Available
logP2.60HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.105 mg/mLALOGPS
logP2.81ALOGPS
logP2.69ChemAxon
logS-3.2ALOGPS
pKa (Strongest Basic)10.24ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.02 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity53.15 m3·mol-1ChemAxon
Polarizability20.19 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9966
Blood Brain Barrier+0.9792
Caco-2 permeable+0.7531
P-glycoprotein substrateNon-substrate0.6627
P-glycoprotein inhibitor INon-inhibitor0.9092
P-glycoprotein inhibitor IINon-inhibitor0.9805
Renal organic cation transporterNon-inhibitor0.8185
CYP450 2C9 substrateNon-substrate0.8464
CYP450 2D6 substrateSubstrate0.5148
CYP450 3A4 substrateNon-substrate0.5233
CYP450 1A2 substrateInhibitor0.6449
CYP450 2C9 inhibitorNon-inhibitor0.8526
CYP450 2D6 inhibitorInhibitor0.8286
CYP450 2C19 inhibitorNon-inhibitor0.752
CYP450 3A4 inhibitorNon-inhibitor0.5737
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7748
Ames testNon AMES toxic0.8728
CarcinogenicityNon-carcinogens0.6055
BiodegradationNot ready biodegradable0.9895
Rat acute toxicity2.8974 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9818
hERG inhibition (predictor II)Non-inhibitor0.738
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 amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenethylamines
Direct Parent
Amphetamines and derivatives
Alternative Parents
Phenylpropanes / Chlorobenzenes / Aralkylamines / Aryl chlorides / Organopnictogen compounds / Organochlorides / Monoalkylamines / Hydrocarbon derivatives
Substituents
Amphetamine or derivatives / Phenylpropane / Aralkylamine / Chlorobenzene / Halobenzene / Aryl chloride / Aryl halide / Amine / Organochloride / Organohalogen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
amphetamines (CHEBI:3646)

Drug created on July 31, 2007 07:10 / Updated on November 02, 2018 08:42