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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 22:08:13 UTC

Update Date

2021-09-26 22:53:11 UTC

HMDB ID

HMDB0245024

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2-Aminopropiophenone

Description

2-aminopropiophenone, also known as cathinone, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Based on a literature review very few articles have been published on 2-aminopropiophenone. This compound has been identified in human blood as reported by (PMID: 31557052 ). 2-aminopropiophenone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2-Aminopropiophenone is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-Aminoethyl phenyl ketone	ChEBI
(-)-alpha-Amino-propiophenone	MeSH
2-Amino-1-phenyl-1-propanone	MeSH
alpha-Aminopropiophenone	MeSH
Cathinine	MeSH
Cathinone	MeSH
Cathinone hydrochloride	MeSH
Cathinone hydrochloride, (+-)-isomer	MeSH
Cathinone hydrochloride, (R)-isomer	MeSH
Cathinone hydrochloride, (S)-isomer	MeSH
Cathinone, (+-)-isomer	MeSH
Cathinone, (S)-isomer	MeSH

Chemical Formula

C₉H₁₁NO

Average Molecular Weight

149.193

Monoisotopic Molecular Weight

149.084063978

IUPAC Name

2-amino-1-phenylpropan-1-one

Traditional Name

2-aminopropiophenone

CAS Registry Number

Not Available

SMILES

CC(N)C(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C9H11NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7H,10H2,1H3

InChI Key

PUAQLLVFLMYYJJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Phenylpropane
Benzoyl
Aryl alkyl ketone
Benzenoid
Monocyclic benzene moiety
Alpha-aminoketone
Hydrocarbon derivative
Amine
Primary amine
Organic nitrogen compound
Organonitrogen compound
Primary aliphatic amine
Organopnictogen compound
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

primary amino compound (CHEBI:59332 )
propanone (CHEBI:59332 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0249706)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.51	ALOGPS
logP	1.18	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	18.65	ChemAxon
pKa (Strongest Basic)	7.55	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	43.09 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	44.31 m³·mol⁻¹	ChemAxon
Polarizability	16.42 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	133.949	30932474
DeepCCS	[M-H]-	130.547	30932474
DeepCCS	[M-2H]-	167.675	30932474
DeepCCS	[M+Na]+	143.213	30932474
AllCCS	[M+H]+	134.4	32859911
AllCCS	[M+H-H2O]+	130.0	32859911
AllCCS	[M+NH4]+	138.4	32859911
AllCCS	[M+Na]+	139.6	32859911
AllCCS	[M-H]-	131.9	32859911
AllCCS	[M+Na-2H]-	133.4	32859911
AllCCS	[M+HCOO]-	135.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	9.9545 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.05 minutes	32390414

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Aminopropiophenone	CC(N)C(=O)C1=CC=CC=C1	1259.5	Standard non polar	33892256
2-Aminopropiophenone	CC(N)C(=O)C1=CC=CC=C1	1259.4	Standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Aminopropiophenone,1TMS,isomer #1	CC(N[Si](C)(C)C)C(=O)C1=CC=CC=C1	1463.2	Semi standard non polar	33892256
2-Aminopropiophenone,1TMS,isomer #1	CC(N[Si](C)(C)C)C(=O)C1=CC=CC=C1	1609.8	Standard non polar	33892256
2-Aminopropiophenone,1TMS,isomer #1	CC(N[Si](C)(C)C)C(=O)C1=CC=CC=C1	1807.9	Standard polar	33892256
2-Aminopropiophenone,2TMS,isomer #1	CC(C(=O)C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	1606.0	Semi standard non polar	33892256
2-Aminopropiophenone,2TMS,isomer #1	CC(C(=O)C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	1668.1	Standard non polar	33892256
2-Aminopropiophenone,2TMS,isomer #1	CC(C(=O)C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	1829.1	Standard polar	33892256
2-Aminopropiophenone,1TBDMS,isomer #1	CC(N[Si](C)(C)C(C)(C)C)C(=O)C1=CC=CC=C1	1691.6	Semi standard non polar	33892256
2-Aminopropiophenone,1TBDMS,isomer #1	CC(N[Si](C)(C)C(C)(C)C)C(=O)C1=CC=CC=C1	1780.2	Standard non polar	33892256
2-Aminopropiophenone,1TBDMS,isomer #1	CC(N[Si](C)(C)C(C)(C)C)C(=O)C1=CC=CC=C1	1955.6	Standard polar	33892256
2-Aminopropiophenone,2TBDMS,isomer #1	CC(C(=O)C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2074.1	Semi standard non polar	33892256
2-Aminopropiophenone,2TBDMS,isomer #1	CC(C(=O)C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2058.9	Standard non polar	33892256
2-Aminopropiophenone,2TBDMS,isomer #1	CC(C(=O)C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2048.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Aminopropiophenone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-3900000000-500e2e9abc6f581520fa	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Aminopropiophenone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Aminopropiophenone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminopropiophenone 10V, Positive-QTOF	splash10-001i-0900000000-6fd043d6580dfaa11fb3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminopropiophenone 20V, Positive-QTOF	splash10-001i-0900000000-17ca9efa8dc1c1d92303	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminopropiophenone 40V, Positive-QTOF	splash10-004i-9100000000-afc8e42ded459cc3c6da	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminopropiophenone 10V, Negative-QTOF	splash10-0002-0900000000-7175f3de7f0b1f0eebc8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminopropiophenone 20V, Negative-QTOF	splash10-055b-2900000000-e1c10eb7bccc188e1436	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminopropiophenone 40V, Negative-QTOF	splash10-004i-9200000000-caadcdbfbb028c57e8e7	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

96940

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

4'-Aminopropiophenone

METLIN ID

Not Available

PubChem Compound

107786

PDB ID

Not Available

ChEBI ID

59332

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 2-Aminopropiophenone (HMDB0245024)

MOL for HMDB0245024 (2-Aminopropiophenone)

3D MOL for HMDB0245024 (2-Aminopropiophenone)

3D SDF for HMDB0245024 (2-Aminopropiophenone)

3D-SDF for HMDB0245024 (2-Aminopropiophenone)

PDB for HMDB0245024 (2-Aminopropiophenone)

3D PDB for HMDB0245024 (2-Aminopropiophenone)

SMILES for HMDB0245024 (2-Aminopropiophenone)

INCHI for HMDB0245024 (2-Aminopropiophenone)

Structure for HMDB0245024 (2-Aminopropiophenone)

3D Structure for HMDB0245024 (2-Aminopropiophenone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra