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Identification
NameChlorphentermine
Accession NumberDB01556
TypeSmall Molecule
GroupsExperimental, Illicit, Withdrawn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
SynonymLanguageCode
4-Chloro-a,a-dimethylbenzeneethanamineNot AvailableNot Available
4-Chloro-a,a-dimethylphenethylamineNot AvailableNot Available
a,a-Dimethyl-p-chlorophenethylamineNot AvailableNot Available
ChlorphenterminumLatinNot Available
ClorfenterminaSpanishNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
ApsedonNot Available
DesopimonNot Available
LucofenNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Chlorphentermine hydrochloride
Thumb
  • InChI Key: WEJDYJKJPUPMLH-UHFFFAOYSA-N
  • Monoisotopic Mass: 219.058154899
  • Average Mass: 220.139
DBSALT000815
Categories
CAS number461-78-9
WeightAverage: 183.678
Monoisotopic: 183.08147716
Chemical FormulaC10H14ClN
InChI KeyZCKAMNXUHHNZLN-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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenethylamines
Direct ParentAmphetamines and derivatives
Alternative Parents
Substituents
  • Amphetamine or derivatives
  • Phenylpropane
  • Aralkylamine
  • Halobenzene
  • Chlorobenzene
  • Aryl halide
  • Aryl chloride
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Primary aliphatic amine
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationUsed as an appetite suppressant.
PharmacodynamicsChlorphentermine 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 actionNot Available
AbsorptionWell absorbed following oral administration.
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half life40 hours
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrateNon-inhibitor0.8526
CYP450 2D6 substrateInhibitor0.8286
CYP450 2C19 substrateNon-inhibitor0.752
CYP450 3A4 substrateNon-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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
boiling point100-102 °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 RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General Reference
  1. GYLYS JA, HART JJ, WARREN MR: Chlorphentermine, a new anorectic agent. J Pharmacol Exp Ther. 1962 Sep;137:365-73. Pubmed
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AminophyllineMay enhance the adverse/toxic effect of other Sympathomimetics.
AmphetamineMay enhance the adverse/toxic effect of other Sympathomimetics.
ArformoterolMay enhance the adverse/toxic effect of other Sympathomimetics.
armodafinilMay enhance the adverse/toxic effect of other Sympathomimetics.
ArticaineMay enhance the adverse/toxic effect of other Sympathomimetics.
AtomoxetineAtoMOXetine may enhance the hypertensive effect of Sympathomimetics. AtoMOXetine may enhance the tachycardic effect of Sympathomimetics.
BenzphetamineMay enhance the adverse/toxic effect of other Sympathomimetics.
CaffeineMay enhance the adverse/toxic effect of other Sympathomimetics.
CocaineMay enhance the adverse/toxic effect of other Sympathomimetics.
DexmethylphenidateMay enhance the adverse/toxic effect of other Sympathomimetics.
DextroamphetamineMay enhance the adverse/toxic effect of other Sympathomimetics.
DiethylpropionMay enhance the adverse/toxic effect of other Sympathomimetics.
DihydrocodeineMay enhance the adverse/toxic effect of other Sympathomimetics.
DipivefrinMay enhance the adverse/toxic effect of other Sympathomimetics.
DobutamineMay enhance the adverse/toxic effect of other Sympathomimetics.
DopamineMay enhance the adverse/toxic effect of other Sympathomimetics.
DoxapramMay enhance the adverse/toxic effect of other Sympathomimetics.
DronabinolCannabinoid-Containing Products may enhance the tachycardic effect of Sympathomimetics.
FenoterolMay enhance the adverse/toxic effect of other Sympathomimetics.
Fluticasone furoateMay enhance the adverse/toxic effect of other Sympathomimetics.
FormoterolMay enhance the adverse/toxic effect of other Sympathomimetics.
IndacaterolMay enhance the adverse/toxic effect of other Sympathomimetics.
IobenguaneMay diminish the therapeutic effect of Iobenguane I 123.
Ipratropium bromideMay enhance the adverse/toxic effect of other Sympathomimetics.
IsomethepteneMay enhance the adverse/toxic effect of other Sympathomimetics.
LevonordefrinMay enhance the adverse/toxic effect of other Sympathomimetics.
LinezolidLinezolid may enhance the hypertensive effect of Sympathomimetics.
LisdexamfetamineMay enhance the adverse/toxic effect of other Sympathomimetics.
MethamphetamineMay enhance the adverse/toxic effect of other Sympathomimetics.
MethylphenidateMay enhance the adverse/toxic effect of other Sympathomimetics.
MidodrineMay enhance the adverse/toxic effect of other Sympathomimetics.
ModafinilMay enhance the adverse/toxic effect of other Sympathomimetics.
NabiloneCannabinoid-Containing Products may enhance the tachycardic effect of Sympathomimetics.
NaphazolineMay enhance the adverse/toxic effect of other Sympathomimetics.
NorepinephrineMay enhance the adverse/toxic effect of other Sympathomimetics.
OrciprenalineMay enhance the adverse/toxic effect of other Sympathomimetics.
OxymetazolineMay enhance the adverse/toxic effect of other Sympathomimetics.
PhendimetrazineMay enhance the adverse/toxic effect of other Sympathomimetics.
PheniramineMay enhance the adverse/toxic effect of other Sympathomimetics.
PhentermineMay enhance the adverse/toxic effect of other Sympathomimetics.
PhenylephrineMay enhance the adverse/toxic effect of other Sympathomimetics.
PirbuterolMay enhance the adverse/toxic effect of other Sympathomimetics.
PropylhexedrineMay enhance the adverse/toxic effect of other Sympathomimetics.
PseudoephedrineMay enhance the adverse/toxic effect of other Sympathomimetics.
SalbutamolMay enhance the adverse/toxic effect of other Sympathomimetics.
SalmeterolMay enhance the adverse/toxic effect of other Sympathomimetics.
Tedizolid PhosphateTedizolid may enhance the hypertensive effect of Sympathomimetics. Tedizolid may enhance the tachycardic effect of Sympathomimetics.
TerbutalineMay enhance the adverse/toxic effect of other Sympathomimetics.
TheophyllineMay enhance the adverse/toxic effect of other Sympathomimetics.
TriprolidineMay enhance the adverse/toxic effect of other Sympathomimetics.
Food InteractionsNot Available
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Drug created on July 31, 2007 07:10 / Updated on September 16, 2013 17:15