NAV

Chlorphentermine

Identification

Generic Name
Chlorphentermine
DrugBank Accession Number
DB01556
Background

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)

Type
Small Molecule
Groups
Illicit, Withdrawn
Structure
3D
Similar Structures
Weight
Average: 183.678
Monoisotopic: 183.08147716
Chemical Formula
C10H14ClN
Synonyms
  • 4-Chloro-a,a-dimethylbenzeneethanamine
  • 4-Chloro-a,a-dimethylphenethylamine
  • a,a-Dimethyl-p-chlorophenethylamine
  • Chlorphentermine
  • Chlorphenterminum
  • Clorfentermina
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Pharmacology

Indication

Used as an appetite suppressant.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Chlorphentermine is a relatively weak stimulant with little abuse potential. It presents a prominent serotonergic profile leading to pulmonary hypertension and cardiac fibrosis after prolonged use. Thus, this drug is no longer used.

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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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interactions in your software
AcebutololThe therapeutic efficacy of Acebutolol can be decreased when used in combination with Chlorphentermine.
AceclofenacThe risk or severity of hypertension can be increased when Chlorphentermine is combined with Aceclofenac.
AcemetacinThe risk or severity of hypertension can be increased when Chlorphentermine is combined with Acemetacin.
AcetazolamideAcetazolamide may decrease the excretion rate of Chlorphentermine which could result in a higher serum level.
AcetophenazineAcetophenazine may decrease the stimulatory activities of Chlorphentermine.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Chlorphentermine hydrochlorideRL11HOJ7DM151-06-4WEJDYJKJPUPMLH-UHFFFAOYSA-N
International/Other Brands
Apsedon / Desopimon / Lucofen

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Amine / Amphetamine or derivatives / Aralkylamine / Aromatic homomonocyclic compound / Aryl chloride / Aryl halide / Chlorobenzene / Halobenzene / Hydrocarbon derivative / Organic nitrogen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
amphetamines (CHEBI:3646)
Affected organisms
Not Available

Chemical Identifiers

UNII
NHW07912O7
CAS number
461-78-9
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

References

General References
  1. GYLYS JA, HART JJ, WARREN MR: Chlorphentermine, a new anorectic agent. J Pharmacol Exp Ther. 1962 Sep;137:365-73. [Article]
KEGG Compound
C07559
PubChem Compound
10007
PubChem Substance
46505599
ChemSpider
9613
BindingDB
85704
ChEBI
3646
ChEMBL
CHEMBL1201269
ZINC
ZINC000000122765
Wikipedia
Chlorphentermine

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

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-MSsplash10-0a4i-9500000000-688c22dbc0d433451811
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-016r-0900000000-711b624e72e64785f050
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0159-0900000000-8de2111fa7decdb61ada
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0900000000-00df956db6d77fbc1f1e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00lr-0900000000-d6cc6c79768922bbd75f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-5900000000-23866fefa15f11529bba
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-056s-5900000000-f7f2b48f863eae870196
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-139.3568
predicted
DeepCCS 1.0 (2019)
[M+H]+142.72458
predicted
DeepCCS 1.0 (2019)
[M+Na]+152.09135
predicted
DeepCCS 1.0 (2019)

Drug created at July 31, 2007 13:10 / Updated at November 03, 2023 23:50