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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:32:11 UTC

Update Date

2021-09-26 22:55:39 UTC

HMDB ID

HMDB0246519

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-Methylthioamphetamine

Description

1-[4-(methylsulfanyl)phenyl]propan-2-amine belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine. Based on a literature review very few articles have been published on 1-[4-(methylsulfanyl)phenyl]propan-2-amine. This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-methylthioamphetamine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-Methylthioamphetamine 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

HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.000   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   12  S   UNK     0       1.334   3.850   0.000  0.00  0.00           S+0
CONECT    1    8                                                            
CONECT    2   12                                                            
CONECT    3    5    9                                                       
CONECT    4    6    9                                                       
CONECT    5    3   10                                                       
CONECT    6    4   10                                                       
CONECT    7    8    9                                                       
CONECT    8    1    7   11                                                  
CONECT    9    3    4    7                                                  
CONECT   10    5    6   12                                                  
CONECT   11    8                                                            
CONECT   12    2   10                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

COMPND    HMDB0246519
HETATM    1  C1  UNL     1       5.206   0.013   0.037  1.00  0.00           C  
HETATM    2  S1  UNL     1       3.981   1.354   0.148  1.00  0.00           S  
HETATM    3  C2  UNL     1       2.304   0.674   0.121  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.634   0.491  -1.052  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.352  -0.030  -1.070  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.283  -0.377   0.095  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.640  -0.926   0.055  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.726   0.104   0.134  1.00  0.00           C  
HETATM    9  C8  UNL     1      -4.060  -0.614   0.081  1.00  0.00           C  
HETATM   10  N1  UNL     1      -2.694   1.034  -0.976  1.00  0.00           N  
HETATM   11  C9  UNL     1       0.386  -0.194   1.279  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.685   0.332   1.300  1.00  0.00           C  
HETATM   13  H1  UNL     1       5.600  -0.198   1.056  1.00  0.00           H  
HETATM   14  H2  UNL     1       6.043   0.402  -0.570  1.00  0.00           H  
HETATM   15  H3  UNL     1       4.814  -0.883  -0.447  1.00  0.00           H  
HETATM   16  H4  UNL     1       2.081   0.745  -2.000  1.00  0.00           H  
HETATM   17  H5  UNL     1      -0.170  -0.169  -2.031  1.00  0.00           H  
HETATM   18  H6  UNL     1      -1.826  -1.536  -0.875  1.00  0.00           H  
HETATM   19  H7  UNL     1      -1.834  -1.654   0.892  1.00  0.00           H  
HETATM   20  H8  UNL     1      -2.706   0.666   1.087  1.00  0.00           H  
HETATM   21  H9  UNL     1      -4.880  -0.001   0.502  1.00  0.00           H  
HETATM   22  H10 UNL     1      -3.966  -1.564   0.612  1.00  0.00           H  
HETATM   23  H11 UNL     1      -4.302  -0.867  -0.983  1.00  0.00           H  
HETATM   24  H12 UNL     1      -1.739   1.418  -1.148  1.00  0.00           H  
HETATM   25  H13 UNL     1      -3.419   1.752  -0.864  1.00  0.00           H  
HETATM   26  H14 UNL     1      -0.069  -0.452   2.232  1.00  0.00           H  
HETATM   27  H15 UNL     1       2.227   0.483   2.223  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3
CONECT    3    4    4   12
CONECT    4    5   16
CONECT    5    6    6   17
CONECT    6    7   11
CONECT    7    8   18   19
CONECT    8    9   10   20
CONECT    9   21   22   23
CONECT   10   24   25
CONECT   11   12   12   26
CONECT   12   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-[4-(Methylsulphanyl)phenyl]propan-2-amine	Generator
alpha-Methyl-P-(methylthio)phenethylamine	MeSH
P-Methylthioamphetamine	MeSH

Chemical Formula

C₁₀H₁₅NS

Average Molecular Weight

181.3

Monoisotopic Molecular Weight

181.092520661

IUPAC Name

1-[4-(methylsulfanyl)phenyl]propan-2-amine

Traditional Name

4-methylthioamphetamine

CAS Registry Number

Not Available

SMILES

CSC1=CC=C(CC(C)N)C=C1

InChI Identifier

InChI=1S/C10H15NS/c1-8(11)7-9-3-5-10(12-2)6-4-9/h3-6,8H,7,11H2,1-2H3

InChI Key

OLEWMKVPSUCNLG-UHFFFAOYSA-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenethylamines

Direct Parent

Amphetamines and derivatives

Alternative Parents

Substituents

Amphetamine or derivatives
Phenylpropane
Aryl thioether
Thiophenol ether
Aralkylamine
Alkylarylthioether
Thioether
Sulfenyl compound
Amine
Primary amine
Organopnictogen compound
Organosulfur compound
Organonitrogen compound
Primary aliphatic amine
Hydrocarbon derivative
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

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	2.52	ALOGPS
logP	2.43	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Basic)	10.01	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	26.02 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	56.46 m³·mol⁻¹	ChemAxon
Polarizability	21.43 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
DeepCCS	[M+H]+	142.95	30932474
DeepCCS	[M-H]-	139.123	30932474
DeepCCS	[M-2H]-	176.591	30932474
DeepCCS	[M+Na]+	152.13	30932474
AllCCS	[M+H]+	139.9	32859911
AllCCS	[M+H-H2O]+	135.7	32859911
AllCCS	[M+NH4]+	143.8	32859911
AllCCS	[M+Na]+	145.0	32859911
AllCCS	[M-H]-	144.8	32859911
AllCCS	[M+Na-2H]-	146.0	32859911
AllCCS	[M+HCOO]-	147.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Methylthioamphetamine	CSC1=CC=C(CC(C)N)C=C1	2227.3	Standard polar	33892256
4-Methylthioamphetamine	CSC1=CC=C(CC(C)N)C=C1	1494.0	Standard non polar	33892256
4-Methylthioamphetamine	CSC1=CC=C(CC(C)N)C=C1	1567.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Methylthioamphetamine,1TMS,isomer #1	CSC1=CC=C(CC(C)N[Si](C)(C)C)C=C1	1750.3	Semi standard non polar	33892256
4-Methylthioamphetamine,1TMS,isomer #1	CSC1=CC=C(CC(C)N[Si](C)(C)C)C=C1	1663.1	Standard non polar	33892256
4-Methylthioamphetamine,1TMS,isomer #1	CSC1=CC=C(CC(C)N[Si](C)(C)C)C=C1	1925.4	Standard polar	33892256
4-Methylthioamphetamine,2TMS,isomer #1	CSC1=CC=C(CC(C)N([Si](C)(C)C)[Si](C)(C)C)C=C1	1888.1	Semi standard non polar	33892256
4-Methylthioamphetamine,2TMS,isomer #1	CSC1=CC=C(CC(C)N([Si](C)(C)C)[Si](C)(C)C)C=C1	1843.1	Standard non polar	33892256
4-Methylthioamphetamine,2TMS,isomer #1	CSC1=CC=C(CC(C)N([Si](C)(C)C)[Si](C)(C)C)C=C1	1969.9	Standard polar	33892256
4-Methylthioamphetamine,1TBDMS,isomer #1	CSC1=CC=C(CC(C)N[Si](C)(C)C(C)(C)C)C=C1	1985.7	Semi standard non polar	33892256
4-Methylthioamphetamine,1TBDMS,isomer #1	CSC1=CC=C(CC(C)N[Si](C)(C)C(C)(C)C)C=C1	1880.8	Standard non polar	33892256
4-Methylthioamphetamine,1TBDMS,isomer #1	CSC1=CC=C(CC(C)N[Si](C)(C)C(C)(C)C)C=C1	2066.6	Standard polar	33892256
4-Methylthioamphetamine,2TBDMS,isomer #1	CSC1=CC=C(CC(C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	2369.1	Semi standard non polar	33892256
4-Methylthioamphetamine,2TBDMS,isomer #1	CSC1=CC=C(CC(C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	2255.8	Standard non polar	33892256
4-Methylthioamphetamine,2TBDMS,isomer #1	CSC1=CC=C(CC(C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	2177.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methylthioamphetamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-8900000000-eb647fea9a669e0ce5d3	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methylthioamphetamine 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 - 4-Methylthioamphetamine 10V, Positive-QTOF	splash10-00lr-0900000000-0dfd1a52ebcca889412c	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylthioamphetamine 20V, Positive-QTOF	splash10-0159-0900000000-1e20e561a1103ccf3f2a	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylthioamphetamine 40V, Positive-QTOF	splash10-00xs-3900000000-c8f285e4f95e1a9ae5ad	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylthioamphetamine 10V, Negative-QTOF	splash10-001i-3900000000-430a56c57d7983feaac0	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylthioamphetamine 20V, Negative-QTOF	splash10-001i-2900000000-af8197908c2ed53c15d6	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylthioamphetamine 40V, Negative-QTOF	splash10-0002-9000000000-3271a04eefe53b210769	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylthioamphetamine 10V, Positive-QTOF	splash10-001i-0900000000-c4d51e99700040bdc15d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylthioamphetamine 20V, Positive-QTOF	splash10-001i-2900000000-e1d23a4dd55efc99690b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylthioamphetamine 40V, Positive-QTOF	splash10-0006-9100000000-f03955395344e76232df	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylthioamphetamine 10V, Negative-QTOF	splash10-001i-0900000000-e3d9888575f8fa44960d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylthioamphetamine 20V, Negative-QTOF	splash10-001r-2900000000-78a68814a399600fb852	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylthioamphetamine 40V, Negative-QTOF	splash10-01bd-8900000000-b9c86ce57c1f10a7b6a5	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

133883

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

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 4-Methylthioamphetamine (HMDB0246519)

MOL for HMDB0246519 (4-Methylthioamphetamine)

3D MOL for HMDB0246519 (4-Methylthioamphetamine)

3D SDF for HMDB0246519 (4-Methylthioamphetamine)

3D-SDF for HMDB0246519 (4-Methylthioamphetamine)

PDB for HMDB0246519 (4-Methylthioamphetamine)

3D PDB for HMDB0246519 (4-Methylthioamphetamine)

SMILES for HMDB0246519 (4-Methylthioamphetamine)

INCHI for HMDB0246519 (4-Methylthioamphetamine)

Structure for HMDB0246519 (4-Methylthioamphetamine)

3D Structure for HMDB0246519 (4-Methylthioamphetamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra