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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:49 UTC
HMDB IDHMDB0015003
Secondary Accession Numbers
  • HMDB15003
Metabolite Identification
Common NameBenzphetamine
DescriptionBenzphetamine is only found in individuals that have used or taken this drug. It is a sympathomimetic agent with properties similar to dextroamphetamine. It is used in the treatment of obesity. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1222)Although 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.
Structure
Data?1582753246
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 Weight239.3553
Monoisotopic Molecular Weight239.167399677
IUPAC Namebenzyl(methyl)[(2S)-1-phenylpropan-2-yl]amine
Traditional Namebenzphetamine
CAS Registry Number156-08-1
SMILES
C[C@@H](CC1=CC=CC=C1)N(C)CC1=CC=CC=C1
InChI Identifier
InChI=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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point152 - 153 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.023 g/LNot Available
LogP4.1Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM154.830932474
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+158.49531661259
DarkChem[M-H]-156.61731661259
DeepCCS[M+H]+158.53630932474
DeepCCS[M-H]-156.15230932474
DeepCCS[M-2H]-189.06230932474
DeepCCS[M+Na]+164.60330932474
AllCCS[M+H]+157.932859911
AllCCS[M+H-H2O]+154.032859911
AllCCS[M+NH4]+161.732859911
AllCCS[M+Na]+162.732859911
AllCCS[M-H]-165.132859911
AllCCS[M+Na-2H]-165.032859911
AllCCS[M+HCOO]-165.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BenzphetamineC[C@@H](CC1=CC=CC=C1)N(C)CC1=CC=CC=C12478.9Standard polar33892256
BenzphetamineC[C@@H](CC1=CC=CC=C1)N(C)CC1=CC=CC=C11874.2Standard non polar33892256
BenzphetamineC[C@@H](CC1=CC=CC=C1)N(C)CC1=CC=CC=C11908.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Benzphetamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dm-6920000000-7c83e10be43beca4a6db2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzphetamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzphetamine LC-ESI-QTOF 35V, positive-QTOFsplash10-0006-9120000000-500b274f6afef32ed4e12020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzphetamine 35V, Positive-QTOFsplash10-0006-9230000000-5fa8f51ec1e6f5ff1d312021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzphetamine 10V, Positive-QTOFsplash10-0006-0190000000-53abd8dba6ec13a440c62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzphetamine 20V, Positive-QTOFsplash10-00kg-3940000000-d297b9cbc93cf306977c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzphetamine 40V, Positive-QTOFsplash10-0006-9400000000-57e6a074201ba0c6f9122016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzphetamine 10V, Negative-QTOFsplash10-000i-0190000000-6a88a2bf83016b16b90c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzphetamine 20V, Negative-QTOFsplash10-000i-0890000000-f2e83357a1507b2d57ea2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzphetamine 40V, Negative-QTOFsplash10-0arv-6900000000-c3eafb9fcd17634ca48e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzphetamine 10V, Positive-QTOFsplash10-0006-0090000000-256c7e14fc77a90805412021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzphetamine 20V, Positive-QTOFsplash10-0006-9560000000-cff805f0fb8a266e219b2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzphetamine 40V, Positive-QTOFsplash10-0006-9100000000-bb878589696e5452d7fb2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzphetamine 10V, Negative-QTOFsplash10-000i-0090000000-a8c0494c6f42c28af7452021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzphetamine 20V, Negative-QTOFsplash10-000i-2290000000-1cd11b6c14d9e0c19ff12021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzphetamine 40V, Negative-QTOFsplash10-00mo-9730000000-a6a72ee74a531f93fa402021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00865 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00865 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00865
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4470556
KEGG Compound IDC07538
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBenzphetamine
METLIN IDNot Available
PubChem Compound5311017
PDB IDNot Available
ChEBI ID3044
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
This enzyme is required for electron transfer from NADP to cytochrome P450 in microsomes. It can also provide electron transfer to heme oxygenase and cytochrome B5.
Gene Name:
POR
Uniprot ID:
P16435
Molecular weight:
77047.575
References
  1. Kanaeva IP, Nikityuk OV, Davydov DR, Dedinskii IR, Koen YM, Kuznetsova GP, Skotselyas ED, Bachmanova GI, Archakov AI: Comparative study of monomeric reconstituted and membrane microsomal monooxygenase systems of the rabbit liver. II. Kinetic parameters of reductase and monooxygenase reactions. Arch Biochem Biophys. 1992 Nov 1;298(2):403-12. [PubMed:1416971 ]
  2. Matsumoto T, Emi Y, Kawabata S, Omura T: Purification and characterization of three male-specific and one female-specific forms of cytochrome P-450 from rat liver microsomes. J Biochem. 1986 Nov;100(5):1359-71. [PubMed:2434473 ]
  3. Kojima H, Takahashi K, Sakane F, Koyama J: Purification and characterization of NADPH-cytochrome c reductase from porcine polymorphonuclear leukocytes. J Biochem. 1987 Nov;102(5):1083-8. [PubMed:3125159 ]
  4. Dutton DR, McMillen SK, Parkinson A: Purification of rat liver microsomal cytochrome P-450b without the use of nonionic detergent. J Biochem Toxicol. 1988 Summer;3:131-45. [PubMed:3148724 ]
  5. Halpert JR, Miller NE, Gorsky LD: On the mechanism of the inactivation of the major phenobarbital-inducible isozyme of rat liver cytochrome P-450 by chloramphenicol. J Biol Chem. 1985 Jul 15;260(14):8397-403. [PubMed:3924914 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Seree EJ, Pisano PJ, Placidi M, Rahmani R, Barra YA: Identification of the human and animal hepatic cytochromes P450 involved in clonazepam metabolism. Fundam Clin Pharmacol. 1993;7(2):69-75. [PubMed:8486332 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular weight:
56277.81
References
  1. Bumpus NN, Sridar C, Kent UM, Hollenberg PF: The naturally occurring cytochrome P450 (P450) 2B6 K262R mutant of P450 2B6 exhibits alterations in substrate metabolism and inactivation. Drug Metab Dispos. 2005 Jun;33(6):795-802. Epub 2005 Mar 15. [PubMed:15769884 ]
  2. Shebley M, Kent UM, Ballou DP, Hollenberg PF: Mechanistic analysis of the inactivation of cytochrome P450 2B6 by phencyclidine: effects on substrate binding, electron transfer, and uncoupling. Drug Metab Dispos. 2009 Apr;37(4):745-52. doi: 10.1124/dmd.108.024661. Epub 2009 Jan 14. [PubMed:19144770 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:
ADRA2A
Uniprot ID:
P08913
Molecular weight:
48956.3
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
General function:
Involved in transmembrane transport
Specific function:
Involved in the ATP-dependent vesicular transport of biogenic amine neurotransmitters. Pumps cytosolic monoamines including dopamine, norepinephrine, serotonin, and histamine into synaptic vesicles. Requisite for vesicular amine storage prior to secretion via exocytosis
Gene Name:
SLC18A2
Uniprot ID:
Q05940
Molecular weight:
55712.1
References
  1. Sulzer D, Chen TK, Lau YY, Kristensen H, Rayport S, Ewing A: Amphetamine redistributes dopamine from synaptic vesicles to the cytosol and promotes reverse transport. J Neurosci. 1995 May;15(5 Pt 2):4102-8. [PubMed:7751968 ]
General function:
Involved in neurotransmitter:sodium symporter activity
Specific function:
Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:
SLC6A3
Uniprot ID:
Q01959
Molecular weight:
68494.255
References
  1. Sulzer D, Sonders MS, Poulsen NW, Galli A: Mechanisms of neurotransmitter release by amphetamines: a review. Prog Neurobiol. 2005 Apr;75(6):406-33. [PubMed:15955613 ]
  2. Kahlig KM, Binda F, Khoshbouei H, Blakely RD, McMahon DG, Javitch JA, Galli A: Amphetamine induces dopamine efflux through a dopamine transporter channel. Proc Natl Acad Sci U S A. 2005 Mar 1;102(9):3495-500. Epub 2005 Feb 22. [PubMed:15728379 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
Gene Name:
ADRA1A
Uniprot ID:
P35348
Molecular weight:
51486.0
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]