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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 22:49:23 UTC

Update Date

2021-09-26 22:54:26 UTC

HMDB ID

HMDB0245770

Secondary Accession Numbers

None

Metabolite Identification

Common Name

alpha-Methyltryptamine

Description

alpha-Methyltryptamine, also known as 3-(2-aminopropyl)indole or indopan, belongs to the class of organic compounds known as 3-alkylindoles. 3-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. Based on a literature review very few articles have been published on alpha-Methyltryptamine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Alpha-methyltryptamine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically alpha-Methyltryptamine 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: 1446                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       7.205  -2.763   0.000  0.00  0.00           N+0
HETATM    2  N   UNK     0       9.668   2.960   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       7.683   1.179   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.205  -0.285   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.190   1.497   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.748  -0.754   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.748  -2.294   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.104  -1.524   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.219   0.350   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414   0.016   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414  -3.064   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.080  -0.754   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.080  -2.294   0.000  0.00  0.00           C+0
CONECT    1    7    8                                                       
CONECT    2    5                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6    8                                                  
CONECT    5    2    3    9                                                  
CONECT    6    4    7   10                                                  
CONECT    7    1    6   11                                                  
CONECT    8    1    4                                                       
CONECT    9    5                                                            
CONECT   10    6   12                                                       
CONECT   11    7   13                                                       
CONECT   12   10   13                                                       
CONECT   13   11   12                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

COMPND    HMDB0245770
HETATM    1  C1  UNL     1      -2.490  -0.316   1.335  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.216   0.417   0.066  1.00  0.00           C  
HETATM    3  N1  UNL     1      -3.442   0.856  -0.588  1.00  0.00           N  
HETATM    4  C3  UNL     1      -1.415  -0.360  -0.935  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.093  -0.753  -0.436  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.269  -2.015  -0.016  1.00  0.00           C  
HETATM    7  N2  UNL     1       1.545  -2.018   0.372  1.00  0.00           N  
HETATM    8  C6  UNL     1       2.009  -0.763   0.205  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.264  -0.249   0.459  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.543   1.080   0.218  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.552   1.894  -0.283  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.298   1.374  -0.536  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.007   0.048  -0.298  1.00  0.00           C  
HETATM   14  H1  UNL     1      -2.827   0.455   2.089  1.00  0.00           H  
HETATM   15  H2  UNL     1      -1.535  -0.722   1.712  1.00  0.00           H  
HETATM   16  H3  UNL     1      -3.283  -1.075   1.270  1.00  0.00           H  
HETATM   17  H4  UNL     1      -1.609   1.325   0.330  1.00  0.00           H  
HETATM   18  H5  UNL     1      -3.752   0.170  -1.318  1.00  0.00           H  
HETATM   19  H6  UNL     1      -3.188   1.732  -1.112  1.00  0.00           H  
HETATM   20  H7  UNL     1      -1.976  -1.213  -1.337  1.00  0.00           H  
HETATM   21  H8  UNL     1      -1.253   0.333  -1.812  1.00  0.00           H  
HETATM   22  H9  UNL     1      -0.368  -2.889   0.003  1.00  0.00           H  
HETATM   23  H10 UNL     1       2.088  -2.855   0.742  1.00  0.00           H  
HETATM   24  H11 UNL     1       4.055  -0.901   0.860  1.00  0.00           H  
HETATM   25  H12 UNL     1       4.526   1.499   0.413  1.00  0.00           H  
HETATM   26  H13 UNL     1       2.785   2.948  -0.471  1.00  0.00           H  
HETATM   27  H14 UNL     1       0.505   1.998  -0.930  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    4   17
CONECT    3   18   19
CONECT    4    5   20   21
CONECT    5    6    6   13
CONECT    6    7   22
CONECT    7    8   23
CONECT    8    9    9   13
CONECT    9   10   24
CONECT   10   11   11   25
CONECT   11   12   26
CONECT   12   13   13   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(1H-indol-3-yl)-2-Propanamine	ChEBI
3-(2-Aminopropyl)indole	ChEBI
alpha-Methyl-1H-indole-3-ethanamine	ChEBI
alpha-Methyl-3-indoleethanamine	ChEBI
alpha-Methyl-beta-indoleethylamine	ChEBI
DL-3-(2-Aminopropyl)indole	ChEBI
Indopan	ChEBI
a-Methyl-1H-indole-3-ethanamine	Generator
Α-methyl-1H-indole-3-ethanamine	Generator
a-Methyl-3-indoleethanamine	Generator
Α-methyl-3-indoleethanamine	Generator
a-Methyl-b-indoleethylamine	Generator
Α-methyl-β-indoleethylamine	Generator
a-Methyltryptamine	Generator
Α-methyltryptamine	Generator

Chemical Formula

C₁₁H₁₄N₂

Average Molecular Weight

174.2423

Monoisotopic Molecular Weight

174.115698458

IUPAC Name

1-(1H-indol-3-yl)propan-2-amine

Traditional Name

α-methyltryptamine

CAS Registry Number

Not Available

SMILES

CC(N)CC1=CNC2=CC=CC=C12

InChI Identifier

InChI=1S/C11H14N2/c1-8(12)6-9-7-13-11-5-3-2-4-10(9)11/h2-5,7-8,13H,6,12H2,1H3

InChI Key

QSQQQURBVYWZKJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Aralkylamine
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organonitrogen compound
Primary aliphatic amine
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tryptamines (CHEBI:59020 )

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	ALOGPS
logP	1.9	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	17.14	ChemAxon
pKa (Strongest Basic)	9.96	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	41.81 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	54.79 m³·mol⁻¹	ChemAxon
Polarizability	20.19 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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-2H]-	172.582	30932474
DeepCCS	[M+Na]+	148.121	30932474
AllCCS	[M+H]+	139.3	32859911
AllCCS	[M+H-H2O]+	134.9	32859911
AllCCS	[M+NH4]+	143.4	32859911
AllCCS	[M+Na]+	144.6	32859911
AllCCS	[M-H]-	142.2	32859911
AllCCS	[M+Na-2H]-	142.7	32859911
AllCCS	[M+HCOO]-	143.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
alpha-Methyltryptamine	CC(N)CC1=CNC2=CC=CC=C12	2915.4	Standard polar	33892256
alpha-Methyltryptamine	CC(N)CC1=CNC2=CC=CC=C12	1732.4	Standard non polar	33892256
alpha-Methyltryptamine	CC(N)CC1=CNC2=CC=CC=C12	1842.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
alpha-Methyltryptamine,1TMS,isomer #1	CC(CC1=C[NH]C2=CC=CC=C12)N[Si](C)(C)C	1883.7	Semi standard non polar	33892256
alpha-Methyltryptamine,1TMS,isomer #1	CC(CC1=C[NH]C2=CC=CC=C12)N[Si](C)(C)C	1843.3	Standard non polar	33892256
alpha-Methyltryptamine,1TMS,isomer #1	CC(CC1=C[NH]C2=CC=CC=C12)N[Si](C)(C)C	2277.4	Standard polar	33892256
alpha-Methyltryptamine,1TMS,isomer #2	CC(N)CC1=CN([Si](C)(C)C)C2=CC=CC=C12	1890.1	Semi standard non polar	33892256
alpha-Methyltryptamine,1TMS,isomer #2	CC(N)CC1=CN([Si](C)(C)C)C2=CC=CC=C12	1936.7	Standard non polar	33892256
alpha-Methyltryptamine,1TMS,isomer #2	CC(N)CC1=CN([Si](C)(C)C)C2=CC=CC=C12	2351.6	Standard polar	33892256
alpha-Methyltryptamine,2TMS,isomer #1	CC(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)N[Si](C)(C)C	1953.0	Semi standard non polar	33892256
alpha-Methyltryptamine,2TMS,isomer #1	CC(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)N[Si](C)(C)C	1973.7	Standard non polar	33892256
alpha-Methyltryptamine,2TMS,isomer #1	CC(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)N[Si](C)(C)C	2100.4	Standard polar	33892256
alpha-Methyltryptamine,2TMS,isomer #2	CC(CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2084.6	Semi standard non polar	33892256
alpha-Methyltryptamine,2TMS,isomer #2	CC(CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2074.6	Standard non polar	33892256
alpha-Methyltryptamine,2TMS,isomer #2	CC(CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2266.6	Standard polar	33892256
alpha-Methyltryptamine,3TMS,isomer #1	CC(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2192.4	Semi standard non polar	33892256
alpha-Methyltryptamine,3TMS,isomer #1	CC(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2166.7	Standard non polar	33892256
alpha-Methyltryptamine,3TMS,isomer #1	CC(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2136.4	Standard polar	33892256
alpha-Methyltryptamine,1TBDMS,isomer #1	CC(CC1=C[NH]C2=CC=CC=C12)N[Si](C)(C)C(C)(C)C	2123.5	Semi standard non polar	33892256
alpha-Methyltryptamine,1TBDMS,isomer #1	CC(CC1=C[NH]C2=CC=CC=C12)N[Si](C)(C)C(C)(C)C	2047.8	Standard non polar	33892256
alpha-Methyltryptamine,1TBDMS,isomer #1	CC(CC1=C[NH]C2=CC=CC=C12)N[Si](C)(C)C(C)(C)C	2386.3	Standard polar	33892256
alpha-Methyltryptamine,1TBDMS,isomer #2	CC(N)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2105.1	Semi standard non polar	33892256
alpha-Methyltryptamine,1TBDMS,isomer #2	CC(N)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2113.6	Standard non polar	33892256
alpha-Methyltryptamine,1TBDMS,isomer #2	CC(N)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2435.5	Standard polar	33892256
alpha-Methyltryptamine,2TBDMS,isomer #1	CC(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)N[Si](C)(C)C(C)(C)C	2395.7	Semi standard non polar	33892256
alpha-Methyltryptamine,2TBDMS,isomer #1	CC(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)N[Si](C)(C)C(C)(C)C	2398.3	Standard non polar	33892256
alpha-Methyltryptamine,2TBDMS,isomer #1	CC(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)N[Si](C)(C)C(C)(C)C	2342.3	Standard polar	33892256
alpha-Methyltryptamine,2TBDMS,isomer #2	CC(CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2554.1	Semi standard non polar	33892256
alpha-Methyltryptamine,2TBDMS,isomer #2	CC(CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2490.0	Standard non polar	33892256
alpha-Methyltryptamine,2TBDMS,isomer #2	CC(CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2418.9	Standard polar	33892256
alpha-Methyltryptamine,3TBDMS,isomer #1	CC(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2835.2	Semi standard non polar	33892256
alpha-Methyltryptamine,3TBDMS,isomer #1	CC(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2771.1	Standard non polar	33892256
alpha-Methyltryptamine,3TBDMS,isomer #1	CC(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2420.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Methyltryptamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-8900000000-3e6ea7e25929a31274e9	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Methyltryptamine 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 - alpha-Methyltryptamine 10V, Positive-QTOF	splash10-056r-0900000000-c5df07dbd39adad8b23b	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Methyltryptamine 20V, Positive-QTOF	splash10-0a6r-0900000000-884f9728d3ba8b5645c3	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Methyltryptamine 40V, Positive-QTOF	splash10-00l6-3900000000-c5e4a82f4f763ab31ab7	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Methyltryptamine 10V, Negative-QTOF	splash10-00di-0900000000-aa836f2a0177d0e17bfb	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Methyltryptamine 20V, Negative-QTOF	splash10-00di-0900000000-f433f885904fad853c62	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Methyltryptamine 40V, Negative-QTOF	splash10-0a4i-2900000000-14c0ba2d6e24e7ad938d	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Methyltryptamine 10V, Positive-QTOF	splash10-056r-0900000000-cb4ec4331e5379fafa91	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Methyltryptamine 20V, Positive-QTOF	splash10-0a4i-1900000000-364e71a7e6a836f99db9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Methyltryptamine 40V, Positive-QTOF	splash10-0fsl-5900000000-ec55cdad08149c7a2432	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Methyltryptamine 10V, Negative-QTOF	splash10-00di-0900000000-b359d04dc6938a3508b3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Methyltryptamine 20V, Negative-QTOF	splash10-00e9-0900000000-5d01ba22939979fbda9c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Methyltryptamine 40V, Negative-QTOF	splash10-014i-0900000000-cc42fe05352137cdc8bf	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

DB01446

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8930

KEGG Compound ID

C20127

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Alpha-Methyltryptamine

METLIN ID

Not Available

PubChem Compound

9287

PDB ID

Not Available

ChEBI ID

59020

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 alpha-Methyltryptamine (HMDB0245770)

MOL for HMDB0245770 (alpha-Methyltryptamine)

3D MOL for HMDB0245770 (alpha-Methyltryptamine)

3D SDF for HMDB0245770 (alpha-Methyltryptamine)

3D-SDF for HMDB0245770 (alpha-Methyltryptamine)

PDB for HMDB0245770 (alpha-Methyltryptamine)

3D PDB for HMDB0245770 (alpha-Methyltryptamine)

SMILES for HMDB0245770 (alpha-Methyltryptamine)

INCHI for HMDB0245770 (alpha-Methyltryptamine)

Structure for HMDB0245770 (alpha-Methyltryptamine)

3D Structure for HMDB0245770 (alpha-Methyltryptamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra