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Record Information
Version2.0
Creation Date2009-07-21 20:27:52 UTC
Update Date2014-12-24 20:25:53 UTC
Accession NumberT3D2919
Identification
Common NameBenzphetamine
ClassSmall Molecule
DescriptionA sympathomimetic agent with properties similar to dextroamphetamine. It is used in the treatment of obesity. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1222)
Compound 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
Synonyms
Synonym
(+)-benzphetamine
(+)-N,alpha-Dimethyl-N-(phenylmethyl)-benzeneethanamine
(+)-N,α-dimethyl-N-(phenylmethyl)-benzeneethanamine
(+)-N-Benzyl-N,alpha-dimethylphenethylamine
(+)-N-benzyl-N,α-dimethylphenethylamine
(AlphaS)-N,alpha-dimethylphenethylamine
(S)-(+)-benzphetamine
(S)-(+)-N-Benzyl-N,alpha-dimethylphenethylamine
(S)-(+)-N-benzyl-N,α-dimethylphenethylamine
(S)-benzphetamine
Benzaphetamine
Benzfetamina
Benzfetamine
Benzfetaminum
Benzylamphetamine
D-N-Methyl-N-benzyl-beta-phenylisopropylamine
d-N-methyl-N-benzyl-β-phenylisopropylamine
Didrex
N-methyl-1-phenyl-N-(phenylmethyl)propan-2-amine
Recede
Regimex
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
SMILES[H][C@](C)(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 KeyInChIKey=YXKTVDFXDRQTKV-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
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point129-130°C
Boiling PointNot Available
SolubilityReadily soluble
LogP4.1
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 RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dm-6920000000-7c83e10be43beca4a6dbJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, positivesplash10-0006-9120000000-500b274f6afef32ed4e1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0006-9230000000-5fa8f51ec1e6f5ff1d31JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0190000000-53abd8dba6ec13a440c6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kg-3940000000-d297b9cbc93cf306977cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9400000000-57e6a074201ba0c6f912JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0190000000-6a88a2bf83016b16b90cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0890000000-f2e83357a1507b2d57eaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0arv-6900000000-c3eafb9fcd17634ca48eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-256c7e14fc77a9080541JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9560000000-cff805f0fb8a266e219bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-bb878589696e5452d7fbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-a8c0494c6f42c28af745JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-2290000000-1cd11b6c14d9e0c19ff1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00mo-9730000000-a6a72ee74a531f93fa40JSpectraViewer
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)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB00865
HMDB IDHMDB15003
PubChem Compound ID5311017
ChEMBL IDCHEMBL1201358
ChemSpider ID4470556
KEGG IDC07538
UniProt IDNot Available
OMIM ID
ChEBI ID3044
BioCyc IDCPD-10530
CTD IDNot Available
Stitch IDBenzphetamine
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkBenzphetamine
References
Synthesis Reference

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

MSDSLink
General References
  1. Wishart DS, Knox C, Guo AC, Cheng D, Shrivastava S, Tzur D, Gautam B, Hassanali M: DrugBank: a knowledgebase for drugs, drug actions and drug targets. Nucleic Acids Res. 2008 Jan;36(Database issue):D901-6. Epub 2007 Nov 29. [18048412 ]
  2. Drugs.com [Link]
  3. RxList: The Internet Drug Index (2009). [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, nad(p)h as one donor, and incorporation of one atom of oxygen
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:
76689.12 Da
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. [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. [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. [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. [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. [3924914 ]
General Function:
Protein heterodimerization activity
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. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine(PE)-stimulated ERK signaling in cardiac myocytes.
Gene Name:
ADRA1A
Uniprot ID:
P35348
Molecular Weight:
51486.005 Da
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. [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. [17016423 ]
General Function:
Thioesterase binding
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:
48956.275 Da
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. [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. [17016423 ]
General Function:
Monoamine transmembrane transporter 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 Da
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. [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. [15728379 ]
General Function:
Monoamine transmembrane transporter activity
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:
55712.075 Da
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. [7751968 ]