Showing Compound Card for Benzphetamine (CDB000565)

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Record Information
Version1.0
Created at2020-03-19 00:44:01 UTC
Updated at2020-12-07 19:07:31 UTC
CannabisDB IDCDB000565
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameBenzphetamine
DescriptionBenzphetamine, also known as didrex, belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine. Benzphetamine is a very strong basic compound (based on its pKa). Benzphetamine is a potentially toxic compound. It is a sympathomimetic agent with properties similar to dextroamphetamine. Benzphetamine is a drug 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. Benzphetamine is only found in individuals that have used or taken this drug. Interestingly, benzphetamine has been reported to be detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499 )
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 Weight239.36
Monoisotopic Molecular Weight239.1674
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 effect

Health effect:

Disposition

Route of exposure:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point152 - 153 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.023 g/LNot Available
logP4.1Not Available
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSBenzphetamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dm-6920000000-7c83e10be43beca4a6dbSpectrum
Predicted GC-MSBenzphetamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, positivesplash10-0006-9120000000-500b274f6afef32ed4e12020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0006-9230000000-5fa8f51ec1e6f5ff1d312021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0190000000-53abd8dba6ec13a440c62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kg-3940000000-d297b9cbc93cf306977c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9400000000-57e6a074201ba0c6f9122016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0190000000-6a88a2bf83016b16b90c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0890000000-f2e83357a1507b2d57ea2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0arv-6900000000-c3eafb9fcd17634ca48e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-256c7e14fc77a90805412021-10-11View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9560000000-cff805f0fb8a266e219b2021-10-11View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-bb878589696e5452d7fb2021-10-11View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-a8c0494c6f42c28af7452021-10-11View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-2290000000-1cd11b6c14d9e0c19ff12021-10-11View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00mo-9730000000-a6a72ee74a531f93fa402021-10-11View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
NADPH--cytochrome P450 reductasePOR7q11.2P16435 details
Alpha-2A adrenergic receptorADRA2A10q24-q26P08913 details
Synaptic vesicular amine transporterSLC18A210q25Q05940 details
Transporters
Protein NameGene NameLocusUniprot IDDetails
Sodium-dependent dopamine transporterSLC6A35p15.3Q01959 details
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
NADPH--cytochrome P450 reductasePOR7q11.2P16435 details
Cytochrome P450 3A4CYP3A47q21.1P08684 details
Cytochrome P450 2B6CYP2B619q13.2P20813 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Alpha-2A adrenergic receptorADRA2A10q24-q26P08913 details
Alpha-1A adrenergic receptorADRA1A8p21.2P35348 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0015003
DrugBank IDDB00865
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General References
  1. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]

Enzymes

Enzyme Details
1. NADPH--cytochrome P450 reductase
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
Enzyme Details
2. Alpha-2A adrenergic receptor
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
Enzyme Details
3. Synaptic vesicular amine transporter
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

Transporters

Enzyme Details
1. Sodium-dependent dopamine transporter
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