Benzphetamine (CHEM002293)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (30)XML
Record Information
Version1.0
Creation Date2009-07-21 20:27:52 UTC
Update Date2026-05-14 16:51:07 UTC
Accession NumberCHEM002293
Identification
Common NameBenzphetamine
ClassSmall Molecule
DescriptionBenzphetamine is an exogenous organic compound with the formula C17H21N and an average molecular weight of 239.36 g/mol. It exists as a solid at room temperature. Benzphetamine belongs to the phenethylamines, a subclass of benzene and substituted derivatives within the organic compounds. This compound functions as a sympathomimetic agent, dopamine uptake inhibitor, and adrenergic uptake inhibitor. It is used as an appetite depressant. Its recorded protein targets include the Alpha-2A adrenergic receptor (ADRA2A), the Alpha-1A adrenergic receptor (ADRA1A), the NADPH--cytochrome P450 reductase (POR), the synaptic vesicular amine transporter (SLC18A2), and the sodium-dependent dopamine transporter (SLC6A3). Regarding its use in treating obesity, benzphetamine and related sympathomimetic medications are thought to produce a decrease in appetite by stimulating the release of dopamine and/or norepinephrine from storage sites in nerve terminals in the lateral hypothalamic feeding center. Benzphetamine has been recorded in two sources: Household cleaning & consumer products (Other Smoking Requisites) and Electrical & Electronic Equipment (Antennas).
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Adrenergic Agent
  • Adrenergic Uptake Inhibitor
  • Amine
  • Central Nervous System Agent
  • Central Nervous System Stimulant
  • Dopamine Agent
  • Dopamine Uptake Inhibitor
  • Drug
  • Metabolite
  • Organic Compound
  • Sympathomimetic
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+)-BenzphetamineChEBI
(+)-N,alpha-Dimethyl-N-(phenylmethyl)-benzeneethanamineChEBI
(+)-N-Benzyl-N,alpha-dimethylphenethylamineChEBI
(AlphaS)-N,alpha-dimethylphenethylamineChEBI
(S)-(+)-BenzphetamineChEBI
(S)-(+)-N-Benzyl-N,alpha-dimethylphenethylamineChEBI
(S)-BenzphetamineChEBI
BenzaphetamineChEBI
BenzfetaminaChEBI
BenzfetamineChEBI
BenzfetaminumChEBI
BenzylamphetamineChEBI
D-N-Methyl-N-benzyl-beta-phenylisopropylamineChEBI
N-Methyl-1-phenyl-N-(phenylmethyl)propan-2-amineChEBI
(+)-N,a-Dimethyl-N-(phenylmethyl)-benzeneethanamineGenerator
(+)-N,Α-dimethyl-N-(phenylmethyl)-benzeneethanamineGenerator
(+)-N-Benzyl-N,a-dimethylphenethylamineGenerator
(+)-N-Benzyl-N,α-dimethylphenethylamineGenerator
(AlphaS)-N,a-dimethylphenethylamineGenerator
(AlphaS)-N,α-dimethylphenethylamineGenerator
(S)-(+)-N-Benzyl-N,a-dimethylphenethylamineGenerator
(S)-(+)-N-Benzyl-N,α-dimethylphenethylamineGenerator
D-N-Methyl-N-benzyl-b-phenylisopropylamineGenerator
D-N-Methyl-N-benzyl-β-phenylisopropylamineGenerator
Pfizer brand OF benzfetamine hydrochlorideHMDB
DidrexHMDB
Chemical FormulaC17H21N
Average Molecular Mass239.355 g/mol
Monoisotopic Mass239.167 g/mol
CAS Registry Number156-08-1
IUPAC Namebenzyl(methyl)[(2S)-1-phenylpropan-2-yl]amine
Traditional Namebenzphetamine
SMILESC[C@@H](CC1=CC=CC=C1)N(C)CC1=CC=CC=C1
InChI IdentifierInChI=1S/C17H21N/c1-15(13-16-9-5-3-6-10-16)18(2)14-17-11-7-4-8-12-17/h3-12,15H,13-14H2,1-2H3/t15-/m0/s1
InChI KeyYXKTVDFXDRQTKV-HNNXBMFYSA-N
Chemical Taxonomy
Description 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
  • Phenylmethylamine
  • Benzylamine
  • Aralkylamine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Benzphetamine Dopamine Reuptake Inhibitor Action PathwaySMP0126989 Not Available
Benzphetamine Drug Metabolism Action PathwaySMP0143301 Not Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point129-130°C
Boiling PointNot Available
SolubilityReadily soluble
Predicted Properties
PropertyValueSource
Water Solubility0.023 g/LALOGPS
logP3.72ALOGPS
logP4.34ChemAxon
logS-4ALOGPS
pKa (Strongest Basic)9.72ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area3.24 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity78.39 m³·mol⁻¹ChemAxon
Polarizability29.03 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dm-6920000000-7c83e10be43beca4a6dbSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, positivesplash10-0006-9120000000-500b274f6afef32ed4e1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0006-9230000000-5fa8f51ec1e6f5ff1d31Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0190000000-53abd8dba6ec13a440c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kg-3940000000-d297b9cbc93cf306977cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9400000000-57e6a074201ba0c6f912Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0190000000-6a88a2bf83016b16b90cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0890000000-f2e83357a1507b2d57eaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0arv-6900000000-c3eafb9fcd17634ca48eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-256c7e14fc77a9080541Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9560000000-cff805f0fb8a266e219bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-bb878589696e5452d7fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-a8c0494c6f42c28af745Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-2290000000-1cd11b6c14d9e0c19ff1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00mo-9730000000-a6a72ee74a531f93fa40Spectrum
Toxicity Profile
Route of ExposureOral. Readily absorbed from the gastro-intestinal tract and buccal mucosa. It Is resistant to metabolism by monoamine oxidase.
Mechanism of ToxicityAlthough the mechanism of action of the sympathomimetic appetite suppressants in the treatment of obesity is not fully known, these medications have pharmacological effects similar to those of amphetamines. Amphetamine and related sympathomimetic medications (such as benzphetamine) are thought to stimulate the release of norepinephrine and/or dopamine from storage sites in nerve terminals in the lateral hypothalamic feeding center, thereby producing a decrease in appetite. This release is mediated by the binding of benzphetamine to centrally located adrenergic receptors.
MetabolismHepatic. Benzphetamine's metabolites include amphetamine and methamphetamine. Half Life: 16 to 31 hours
Toxicity ValuesLD50: 160 mg/kg (Oral, Rat) (1)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the management of exogenous obesity as a short term adjunct (a few weeks) in a regimen of weight reduction based on caloric restriction
Minimum Risk LevelNot Available
Health EffectsUsing large amounts of these drugs can result in a condition known as amphetamine psychosis -- which can result in auditory, visual and tactile hallucinations, intense paranoia, irrational thoughts and beliefs, delusions, and mental confusion.
SymptomsAcute overdosage may result in restlessness, tremor, tachypnea, confusion, assaultiveness, and panic states.
TreatmentManagement of acute amphetamine intoxication is largely symptomatic and includes sedation with a barbiturate. If hypertension is marked, the use of a nitrite or rapidly acting alpha receptor blocking agent should be considered. Acidification of the urine increases amphetamine excretion. (3)
Concentrations
Not Available
DrugBank IDDB00865
HMDB IDHMDB0015003
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBenzphetamine
Chemspider ID4470556
ChEBI ID3044
PubChem Compound ID5311017
Kegg Compound IDC07538
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Dennis J. Kalota, Keith G. Tomazi, “Crystallization Method for Benzphetamine.” U.S. Patent US20080262268, issued October 23, 2008.

MSDSLink
General ReferencesNot Available