Phenethylamine

Identification

Name
Phenethylamine
Accession Number
DB04325  (EXPT02542)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • 2-phenylethylamine
  • benzeneethanamine
  • beta-Phenylethylamine
  • Phenylethylamine
  • β-aminoethylbenzene
  • β-phenethylamine
External IDs
FEMA NO. 3220
Categories
UNII
327C7L2BXQ
CAS number
64-04-0
Weight
Average: 121.1796
Monoisotopic: 121.089149357
Chemical Formula
C8H11N
InChI Key
BHHGXPLMPWCGHP-UHFFFAOYSA-N
InChI
InChI=1S/C8H11N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6-7,9H2
IUPAC Name
2-phenylethan-1-amine
SMILES
NCCC1=CC=CC=C1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UPrimary amine oxidaseNot AvailableEscherichia coli (strain K12)
UTrypsin-2Not AvailableHuman
UTrypsin-1Not AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Phenylethylamine MetabolismMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Phenethylamine is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when 3,4-Methylenedioxyamphetamine is combined with Phenethylamine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Phenethylamine.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Phenethylamine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Phenethylamine is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when 7-Nitroindazole is combined with Phenethylamine.
AcepromazineThe risk or severity of adverse effects can be increased when Acepromazine is combined with Phenethylamine.
AceprometazineThe risk or severity of adverse effects can be increased when Aceprometazine is combined with Phenethylamine.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Phenethylamine.
AcetophenazineThe risk or severity of adverse effects can be increased when Acetophenazine is combined with Phenethylamine.
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0012275
KEGG Compound
C05332
PubChem Compound
1001
PubChem Substance
46507825
ChemSpider
13856352
BindingDB
10758
ChEBI
18397
ChEMBL
CHEMBL610
HET
PEA
Wikipedia
2-phenylethylamine

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)-60 °CPhysProp
boiling point (°C)197.5 °CPhysProp
logP1.41HANSCH,C ET AL. (1995)
pKa9.83 (at 25 °C)CRC Handbook Chem Physics (2000)
Predicted Properties
PropertyValueSource
Water Solubility2.19 mg/mLALOGPS
logP1.41ALOGPS
logP1.39ChemAxon
logS-1.7ALOGPS
pKa (Strongest Basic)9.79ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.02 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity39.29 m3·mol-1ChemAxon
Polarizability14.35 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9022
Blood Brain Barrier+0.9358
Caco-2 permeable+0.8705
P-glycoprotein substrateNon-substrate0.7267
P-glycoprotein inhibitor INon-inhibitor0.9586
P-glycoprotein inhibitor IINon-inhibitor0.9273
Renal organic cation transporterNon-inhibitor0.5524
CYP450 2C9 substrateNon-substrate0.8336
CYP450 2D6 substrateSubstrate0.6961
CYP450 3A4 substrateNon-substrate0.7843
CYP450 1A2 substrateInhibitor0.7527
CYP450 2C9 inhibitorNon-inhibitor0.7402
CYP450 2D6 inhibitorInhibitor0.6126
CYP450 2C19 inhibitorInhibitor0.5132
CYP450 3A4 inhibitorNon-inhibitor0.9109
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6645
Ames testNon AMES toxic0.8619
CarcinogenicityNon-carcinogens0.7581
BiodegradationReady biodegradable0.9225
Rat acute toxicity2.2561 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6231
hERG inhibition (predictor II)Non-inhibitor0.8105
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-0udi-3900000000-c931498c67dbf88820ee
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-00dr-5900000000-d15a3c803d2534e366d8
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-001i-9000000000-7713ab7346491f1f5f42
GC-MS Spectrum - EI-BGC-MSsplash10-001i-9000000000-94774bbd6283b4a26a51
GC-MS Spectrum - CI-BGC-MSsplash10-0abc-5900000000-724c680a9564ac27f7ee
GC-MS Spectrum - EI-BGC-MSsplash10-001i-9000000000-5ba434a8565ec0014b6b
GC-MS Spectrum - EI-BGC-MSsplash10-053r-9000000000-f312ab6fe99f8eca86e7
GC-MS Spectrum - GC-MSGC-MSsplash10-0udi-3900000000-c931498c67dbf88820ee
GC-MS Spectrum - GC-MSGC-MSsplash10-00dr-5900000000-d15a3c803d2534e366d8
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00dr-4900000000-4c37abb4c50d5582d87c
Mass Spectrum (Electron Ionization)MSsplash10-001i-9000000000-bf5d1e8f4a14683bd0aa
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-05fr-0900000000-10a3aff16ce06e5488bb
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-1900000000-c8186da6e772bfd9759c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a6r-9500000000-2745e56fb8603507394b
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0900000000-b746d7d1eb593614d234
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-1900000000-f4ada8157d6dde803051
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ufu-9500000000-54d2d2a1b68d878200b8
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0900000000-95c5a1366bba1014e2aa
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0ab9-0900000000-5ad03d29c0ff6167539c
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4i-0900000000-1b25fe0d03af3ce715ba
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-056r-7900000000-a6478bab1f5bd04c7329
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-004i-9100000000-abdacae4bceb2048614f
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-004i-9000000000-d61f8f9b0d593297d010
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0ab9-0900000000-e3d2be06e661bac2f739
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4i-0900000000-fc4c40ae6333ed1f04f6
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-056r-7900000000-f25cc18055d08500ec9d
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-004i-9100000000-0e8ece94eaa349e6fd21
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0uk9-2900000000-272fff4a446fcf053de8
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0900000000-e833e9ebdd0584ee9cff
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0900000000-f51c34f8fd6e67925a52
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0900000000-162188a06251a43ccc54
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0900000000-162188a06251a43ccc54
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0900000000-2a12817c62551d9dee50
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0900000000-ac8b555024a8bbc5e78b
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0900000000-926231c14695be35af04
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0900000000-c5e8005c53eaf96bc957
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0900000000-6f9e6a6eb6c2ac8f4531
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-1900000000-aeb026a07351a147ae19
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-3900000000-a6c6357f047322c4efe1
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-0a6r-6900000000-0a32d01e2dda19a78c83
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-056r-9600000000-be832e76b1211d35978c
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-004i-9400000000-ab97002137a57a7802bc
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-0a4i-0900000000-2a12817c62551d9dee50
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-0a4i-0900000000-2a12817c62551d9dee50
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-0a4i-0900000000-2a12817c62551d9dee50
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-0a4i-0900000000-2a12817c62551d9dee50
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-0a4i-0900000000-2a12817c62551d9dee50
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-0a4i-0900000000-ebae5d6c62b8ee370881
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-0a4i-0900000000-59c9e4b732cefb980d7a
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-0a4i-0900000000-26480187df9af12b5e51
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-0a4i-0900000000-80cc5c508682030dd54d
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-0a4i-0900000000-96f8c21f43cd5c8241b6
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-0a4i-2900000000-7b8b85f18e1e2649a01a
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-0a6r-5900000000-7824387b03757f7327b5
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-056s-9400000000-70692f6e709a0a582c39
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-004j-9200000000-35e7dc8a4c05ad6b2085
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-0900000000-9c0eb4bb55c5eb0d2f87
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenethylamines. These are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenethylamines
Direct Parent
Phenethylamines
Alternative Parents
2-arylethylamines / Aralkylamines / Organopnictogen compounds / Monoalkylamines / Hydrocarbon derivatives
Substituents
Phenethylamine / 2-arylethylamine / Aralkylamine / Organic nitrogen compound / Organopnictogen compound / Hydrocarbon derivative / Primary amine / Organonitrogen compound / Primary aliphatic amine / Amine
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
alkaloid, aralkylamine, phenylethylamine (CHEBI:18397) / Biogenic amines (C05332)

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Tryptamine:oxygen oxidoreductase (deaminating) activity
Specific Function
The enzyme prefers aromatic over aliphatic amines.
Gene Name
tynA
Uniprot ID
P46883
Uniprot Name
Primary amine oxidase
Molecular Weight
84378.17 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. [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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Serine-type endopeptidase activity
Specific Function
In the ileum, may be involved in defensin processing, including DEFA5.
Gene Name
PRSS2
Uniprot ID
P07478
Uniprot Name
Trypsin-2
Molecular Weight
26487.55 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. [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]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Serine-type endopeptidase activity
Specific Function
Has activity against the synthetic substrates Boc-Phe-Ser-Arg-Mec, Boc-Leu-Thr-Arg-Mec, Boc-Gln-Ala-Arg-Mec and Boc-Val-Pro-Arg-Mec. The single-chain form is more active than the two-chain form aga...
Gene Name
PRSS1
Uniprot ID
P07477
Uniprot Name
Trypsin-1
Molecular Weight
26557.88 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. [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]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 05:55