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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:30:44 UTC

Update Date

2021-09-26 22:55:37 UTC

HMDB ID

HMDB0246494

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-Methoxyamphetamine

Description

4-Methoxyamphetamine belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine. 4-Methoxyamphetamine has been detected, but not quantified in, potatos (Solanum tuberosum). This could make 4-methoxyamphetamine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 4-Methoxyamphetamine. This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-methoxyamphetamine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-Methoxyamphetamine 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                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1472                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       4.414  -4.089   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       5.748   4.381   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       4.414   2.071   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.748   2.841   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.414   0.531   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.081   2.071   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.748  -0.239   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.080  -0.239   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.748  -1.779   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.080  -1.779   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414  -2.549   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.080  -4.859   0.000  0.00  0.00           C+0
CONECT    1   11   12                                                       
CONECT    2    4                                                            
CONECT    3    4    5                                                       
CONECT    4    2    3    6                                                  
CONECT    5    3    7    8                                                  
CONECT    6    4                                                            
CONECT    7    5    9                                                       
CONECT    8    5   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   11                                                       
CONECT   11    1    9   10                                                  
CONECT   12    1                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

COMPND    HMDB0246996
HETATM    1  C1  UNL     1       4.467   0.464  -0.118  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.666  -0.624   0.338  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.307  -0.626   0.066  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.722   0.409  -0.639  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.368   0.397  -0.905  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.371  -0.676  -0.446  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.829  -0.698  -0.726  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.562  -0.015   0.396  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.113   1.418   0.534  1.00  0.00           C  
HETATM   10  N1  UNL     1      -3.988  -0.022   0.168  1.00  0.00           N  
HETATM   11  C9  UNL     1       0.226  -1.718   0.266  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.581  -1.703   0.531  1.00  0.00           C  
HETATM   13  H1  UNL     1       5.538   0.246   0.033  1.00  0.00           H  
HETATM   14  H2  UNL     1       4.307   0.554  -1.208  1.00  0.00           H  
HETATM   15  H3  UNL     1       4.141   1.348   0.456  1.00  0.00           H  
HETATM   16  H4  UNL     1       2.317   1.260  -1.003  1.00  0.00           H  
HETATM   17  H5  UNL     1      -0.110   1.206  -1.461  1.00  0.00           H  
HETATM   18  H6  UNL     1      -2.177  -1.743  -0.809  1.00  0.00           H  
HETATM   19  H7  UNL     1      -1.991  -0.187  -1.678  1.00  0.00           H  
HETATM   20  H8  UNL     1      -2.378  -0.570   1.347  1.00  0.00           H  
HETATM   21  H9  UNL     1      -2.224   1.888  -0.466  1.00  0.00           H  
HETATM   22  H10 UNL     1      -2.828   1.918   1.231  1.00  0.00           H  
HETATM   23  H11 UNL     1      -1.110   1.501   0.949  1.00  0.00           H  
HETATM   24  H12 UNL     1      -4.201   0.599  -0.636  1.00  0.00           H  
HETATM   25  H13 UNL     1      -4.429   0.431   1.011  1.00  0.00           H  
HETATM   26  H14 UNL     1      -0.383  -2.551   0.617  1.00  0.00           H  
HETATM   27  H15 UNL     1       2.054  -2.507   1.083  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
beta-Methoxyamphetamine	HMDB
b-Methoxyamphetamine	HMDB
Β-methoxyamphetamine	HMDB
4-Methoxyamphetamine sulfate	HMDB
4-Methoxyamphetamine, (+-)-isomer	HMDB
4-Methoxyamphetamine, (R)-isomer	HMDB
p-Methoxyamphetamine	HMDB
4-Methoxyamphetamine hydrochloride, (S)-isomer	HMDB
4-Methoxyamphetamine, (S)-isomer	HMDB
p-Methoxy-alpha-methylphenethylamine	HMDB
Para-methoxyamphetamine	HMDB
4-Methoxyamphetamine hydrochloride	HMDB
4-Methoxyamphetamine hydrochloride, (+-)-isomer	HMDB
4-Methoxyamphetamine hydrochloride, (R)-isomer	HMDB
Paramethoxyamphetamine	HMDB

Chemical Formula

C₁₀H₁₅NO

Average Molecular Weight

165.2322

Monoisotopic Molecular Weight

165.115364107

IUPAC Name

1-(4-methoxyphenyl)propan-2-amine

Traditional Name

P-methoxyamphetamine

CAS Registry Number

Not Available

SMILES

COC1=CC=C(CC(C)N)C=C1

InChI Identifier

InChI=1S/C10H15NO/c1-8(11)7-9-3-5-10(12-2)6-4-9/h3-6,8H,7,11H2,1-2H3

InChI Key

NEGYEDYHPHMHGK-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
Anisole
Phenol ether
Phenoxy compound
Methoxybenzene
Aralkylamine
Alkyl aryl ether
Ether
Primary amine
Organic nitrogen compound
Amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (FooDB: )

Food

Vegetable

Tuber

Potato (FooDB: FOOD00175)

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	1.74	ALOGPS
logP	1.65	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Basic)	10.04	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	35.25 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	50.17 m³·mol⁻¹	ChemAxon
Polarizability	19.29 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]+	140.462	30932474
DeepCCS	[M-H]-	136.634	30932474
DeepCCS	[M-2H]-	174.196	30932474
DeepCCS	[M+Na]+	149.734	30932474
AllCCS	[M+H]+	137.6	32859911
AllCCS	[M+H-H2O]+	133.2	32859911
AllCCS	[M+NH4]+	141.6	32859911
AllCCS	[M+Na]+	142.8	32859911
AllCCS	[M-H]-	139.9	32859911
AllCCS	[M+Na-2H]-	141.1	32859911
AllCCS	[M+HCOO]-	142.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	10.4847 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.04 minutes	32390414

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Methoxyamphetamine	COC1=CC=C(CC(C)N)C=C1	1404.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Methoxyamphetamine,1TMS,isomer #1	COC1=CC=C(CC(C)N[Si](C)(C)C)C=C1	1545.4	Semi standard non polar	33892256
4-Methoxyamphetamine,1TMS,isomer #1	COC1=CC=C(CC(C)N[Si](C)(C)C)C=C1	1545.5	Standard non polar	33892256
4-Methoxyamphetamine,1TMS,isomer #1	COC1=CC=C(CC(C)N[Si](C)(C)C)C=C1	1912.1	Standard polar	33892256
4-Methoxyamphetamine,2TMS,isomer #1	COC1=CC=C(CC(C)N([Si](C)(C)C)[Si](C)(C)C)C=C1	1754.5	Semi standard non polar	33892256
4-Methoxyamphetamine,2TMS,isomer #1	COC1=CC=C(CC(C)N([Si](C)(C)C)[Si](C)(C)C)C=C1	1766.5	Standard non polar	33892256
4-Methoxyamphetamine,2TMS,isomer #1	COC1=CC=C(CC(C)N([Si](C)(C)C)[Si](C)(C)C)C=C1	1947.0	Standard polar	33892256
4-Methoxyamphetamine,1TBDMS,isomer #1	COC1=CC=C(CC(C)N[Si](C)(C)C(C)(C)C)C=C1	1796.8	Semi standard non polar	33892256
4-Methoxyamphetamine,1TBDMS,isomer #1	COC1=CC=C(CC(C)N[Si](C)(C)C(C)(C)C)C=C1	1784.3	Standard non polar	33892256
4-Methoxyamphetamine,1TBDMS,isomer #1	COC1=CC=C(CC(C)N[Si](C)(C)C(C)(C)C)C=C1	2048.5	Standard polar	33892256
4-Methoxyamphetamine,2TBDMS,isomer #1	COC1=CC=C(CC(C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	2220.1	Semi standard non polar	33892256
4-Methoxyamphetamine,2TBDMS,isomer #1	COC1=CC=C(CC(C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	2176.0	Standard non polar	33892256
4-Methoxyamphetamine,2TBDMS,isomer #1	COC1=CC=C(CC(C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	2145.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methoxyamphetamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9700000000-876eb781b532ecce8226	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methoxyamphetamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methoxyamphetamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methoxyamphetamine 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-Methoxyamphetamine 10V, Positive-QTOF	splash10-014j-0900000000-b680ee40bd095675b913	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methoxyamphetamine 20V, Positive-QTOF	splash10-00kb-0900000000-2481399cc6def79573d8	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methoxyamphetamine 40V, Positive-QTOF	splash10-015c-4900000000-16b938d7f7ae439b4d1e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methoxyamphetamine 10V, Negative-QTOF	splash10-03di-0900000000-6428f777f5e960e5908e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methoxyamphetamine 20V, Negative-QTOF	splash10-03di-0900000000-2599bad4f4523458850f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methoxyamphetamine 40V, Negative-QTOF	splash10-00l2-2900000000-e5de3dabba0d7ff286d9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methoxyamphetamine 10V, Positive-QTOF	splash10-014i-1900000000-0ca07d0b345963ca3c6c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methoxyamphetamine 20V, Positive-QTOF	splash10-00xr-3900000000-ac739fc99b2103ec3a48	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methoxyamphetamine 40V, Positive-QTOF	splash10-004l-9200000000-68a6ef19d08ef98dade6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methoxyamphetamine 10V, Negative-QTOF	splash10-0229-0900000000-1515a440dfe22d85bac2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methoxyamphetamine 20V, Negative-QTOF	splash10-08ml-1900000000-fddfa0469e01375f7e2b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methoxyamphetamine 40V, Negative-QTOF	splash10-0536-5900000000-16887d3fed37ca94e199	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

DB01472

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001873

KNApSAcK ID

Not Available

Chemspider ID

29417

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Para-Methoxyamphetamine

METLIN ID

Not Available

PubChem Compound

31721

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-Methoxyamphetamine (HMDB0246494)

MOL for HMDB0246494 (4-Methoxyamphetamine)

3D MOL for HMDB0246494 (4-Methoxyamphetamine)

3D SDF for HMDB0246494 (4-Methoxyamphetamine)

3D-SDF for HMDB0246494 (4-Methoxyamphetamine)

PDB for HMDB0246494 (4-Methoxyamphetamine)

3D PDB for HMDB0246494 (4-Methoxyamphetamine)

SMILES for HMDB0246494 (4-Methoxyamphetamine)

INCHI for HMDB0246494 (4-Methoxyamphetamine)

Structure for HMDB0246494 (4-Methoxyamphetamine)

3D Structure for HMDB0246494 (4-Methoxyamphetamine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra