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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:48:23 UTC

Update Date

2023-02-21 17:29:02 UTC

HMDB ID

HMDB0041927

Secondary Accession Numbers

HMDB41927

Metabolite Identification

Common Name

Methcathinone

Description

Injecting this substance has recently been associated with symptoms similar to those seen in patients with Parkinson's Disease (Manganism) due to the compound manganese dioxide which is a byproduct of synthesis with permanganate. Methcathinone (α-methylamino-propiophenone or ephedrone) is a psychoactive stimulant, sometimes used as a recreational drug and considered addictive. It is usually snorted, but can be smoked, injected, or taken orally. Methcathinone is currently a DEA Schedule I controlled substance in the United States. Methcathinone is a beta-keto N-methylampthetamine and is closely related to the naturally occurring compounds, cathinone and cathine. It is also very closely related to methamphetamine, differing by only the ketone substituent and differing from amphetamine by both a keto and N-methyl substituent. The C=O bond at the R-position (directly right of the benzene ring) is slightly polar, and as a result the drug does not cross the lipid blood-brain barrier quite as well as amphetamine. Nevertheless, it is a potent CNS stimulant and dopamine reuptake inhibitor. Chronic high dosage use may result in acute mental confusion ranging from mild paranoia to psychosis. These symptoms typically disappear quickly if use is stopped.

Structure

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

HEADER    PROTEIN                                 13-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-12         0                                  
HETATM    1  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       0.000   6.160   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2   11                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    9                                                       
CONECT    7    5    9                                                       
CONECT    8    1   10   11                                                  
CONECT    9    6    7   10                                                  
CONECT   10    8    9   12                                                  
CONECT   11    2    8                                                       
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-(Methylamino)-1-phenyl-1-propanone	HMDB
2-(Methylamino)propiophenone	HMDB
2-Methylamino-1-phenylpropanone	HMDB
alpha-Methylaminopropiophenone	HMDB
Cat	HMDB
Ephedrone	HMDB
Monomethylpropion	HMDB
Monomethylpropion hydrochloride, 14C-labeled	HMDB
Methcathinone	MeSH

Chemical Formula

C₁₀H₁₃NO

Average Molecular Weight

163.2163

Monoisotopic Molecular Weight

163.099714043

IUPAC Name

2-(methylamino)-1-phenylpropan-1-one

Traditional Name

methcathinone

CAS Registry Number

5650-44-2

SMILES

CNC(C)C(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C10H13NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,11H,1-2H3

InChI Key

LPLLVINFLBSFRP-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
Secondary amine
Secondary aliphatic amine
Hydrocarbon derivative
Amine
Organic nitrogen compound
Organonitrogen compound
Organopnictogen compound
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Not Available

Not Available

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
Water Solubility	2.22 g/L	ALOGPS
logP	1.01	ALOGPS
logP	1.61	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	18.52	ChemAxon
pKa (Strongest Basic)	8.02	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.1 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	49.09 m³·mol⁻¹	ChemAxon
Polarizability	18.4 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	137.921	31661259
DarkChem	[M-H]-	136.378	31661259
DeepCCS	[M+H]+	136.332	30932474
DeepCCS	[M-H]-	133.27	30932474
DeepCCS	[M-2H]-	170.145	30932474
DeepCCS	[M+Na]+	145.683	30932474
AllCCS	[M+H]+	136.1	32859911
AllCCS	[M+H-H2O]+	131.7	32859911
AllCCS	[M+NH4]+	140.2	32859911
AllCCS	[M+Na]+	141.4	32859911
AllCCS	[M-H]-	137.7	32859911
AllCCS	[M+Na-2H]-	138.9	32859911
AllCCS	[M+HCOO]-	140.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methcathinone	CNC(C)C(=O)C1=CC=CC=C1	1816.7	Standard polar	33892256
Methcathinone	CNC(C)C(=O)C1=CC=CC=C1	1330.9	Standard non polar	33892256
Methcathinone	CNC(C)C(=O)C1=CC=CC=C1	1345.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Methcathinone,1TMS,isomer #1	CC(C(=O)C1=CC=CC=C1)N(C)[Si](C)(C)C	1510.8	Semi standard non polar	33892256
Methcathinone,1TMS,isomer #1	CC(C(=O)C1=CC=CC=C1)N(C)[Si](C)(C)C	1543.7	Standard non polar	33892256
Methcathinone,1TBDMS,isomer #1	CC(C(=O)C1=CC=CC=C1)N(C)[Si](C)(C)C(C)(C)C	1754.8	Semi standard non polar	33892256
Methcathinone,1TBDMS,isomer #1	CC(C(=O)C1=CC=CC=C1)N(C)[Si](C)(C)C(C)(C)C	1739.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Methcathinone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9600000000-6c14437af014bdcfb878	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methcathinone 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 - Methcathinone 10V, Positive-QTOF	splash10-03di-0900000000-b830f4b3c6a469752107	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methcathinone 20V, Positive-QTOF	splash10-08fr-2900000000-f94999162ca270995fb4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methcathinone 40V, Positive-QTOF	splash10-0a4i-9200000000-498262f56f4584950115	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methcathinone 10V, Negative-QTOF	splash10-03di-0900000000-8a1da11eaefe5666ab20	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methcathinone 20V, Negative-QTOF	splash10-03di-2900000000-5683bb883eb6d0a34749	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methcathinone 40V, Negative-QTOF	splash10-057i-9700000000-963d03c02efd93af20b4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methcathinone 10V, Positive-QTOF	splash10-0002-0900000000-4fc7a5033b98bea30010	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methcathinone 20V, Positive-QTOF	splash10-0002-0900000000-c7048f9f6e93d1740d1d	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methcathinone 40V, Positive-QTOF	splash10-0059-8900000000-6dfb5e90314b491664e1	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methcathinone 10V, Negative-QTOF	splash10-03di-0900000000-3ff27c7ea240804db12c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methcathinone 20V, Negative-QTOF	splash10-01q9-2900000000-5ce17c5ed9868c9636b9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methcathinone 40V, Negative-QTOF	splash10-004i-9100000000-095e2d12cafae77ce952	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

1519

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Methcathinone

METLIN ID

Not Available

PubChem Compound

1576

PDB ID

Not Available

ChEBI ID

149677

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

Not Available

Showing metabocard for Methcathinone (HMDB0041927)

MOL for HMDB0041927 (Methcathinone)

3D MOL for HMDB0041927 (Methcathinone)

3D SDF for HMDB0041927 (Methcathinone)

3D-SDF for HMDB0041927 (Methcathinone)

PDB for HMDB0041927 (Methcathinone)

3D PDB for HMDB0041927 (Methcathinone)

SMILES for HMDB0041927 (Methcathinone)

INCHI for HMDB0041927 (Methcathinone)

Structure for HMDB0041927 (Methcathinone)

3D Structure for HMDB0041927 (Methcathinone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra