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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:18:22 UTC

Update Date

2021-09-26 22:51:38 UTC

HMDB ID

HMDB0244116

Secondary Accession Numbers

None

Metabolite Identification

Common Name

1,2,3,4-Tetrahydro-1-naphthylamine

Description

1,2,3,4-tetrahydronaphthalen-1-amine belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane. 1,2,3,4-tetrahydronaphthalen-1-amine is a very strong basic compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). 1,2,3,4-tetrahydro-1-naphthylamine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 1,2,3,4-Tetrahydro-1-naphthylamine 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 Stereo Labels

Synonyms

Value	Source
1-Aminotetralin, (+-)-isomer	MeSH
1-Aminotetralin	MeSH
1-Aminotetrahydronaphthalene	MeSH
1-Aminotetralin hydrochloride	MeSH

Chemical Formula

C₁₀H₁₃N

Average Molecular Weight

147.221

Monoisotopic Molecular Weight

147.104799423

IUPAC Name

1,2,3,4-tetrahydronaphthalen-1-amine

Traditional Name

1,2,3,4-tetrahydronaphthalen-1-amine

CAS Registry Number

Not Available

SMILES

NC1CCCC2=CC=CC=C12

InChI Identifier

InChI=1S/C10H13N/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-2,4,6,10H,3,5,7,11H2

InChI Key

JRZGPXSSNPTNMA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Tetralins

Sub Class

Not Available

Direct Parent

Tetralins

Alternative Parents

Substituents

Tetralin
Aralkylamine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organonitrogen compound
Primary aliphatic amine
Amine
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	1.95	ALOGPS
logP	2.09	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Basic)	9.55	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	0	ChemAxon
Refractivity	46.71 m³·mol⁻¹	ChemAxon
Polarizability	17.26 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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-2H]-	165.628	30932474
DeepCCS	[M+Na]+	140.636	30932474
AllCCS	[M+H]+	133.4	32859911
AllCCS	[M+H-H2O]+	128.8	32859911
AllCCS	[M+NH4]+	137.7	32859911
AllCCS	[M+Na]+	139.0	32859911
AllCCS	[M-H]-	134.0	32859911
AllCCS	[M+Na-2H]-	135.0	32859911
AllCCS	[M+HCOO]-	136.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	2.74 minutes	32390414
Predicted by Siyang on May 30, 2022	10.7064 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.65 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1192.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	347.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	134.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	211.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	140.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	364.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	362.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	320.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	931.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	328.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	953.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	249.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	277.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	501.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	297.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	74.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,2,3,4-Tetrahydro-1-naphthylamine	NC1CCCC2=CC=CC=C12	1900.9	Standard polar	33892256
1,2,3,4-Tetrahydro-1-naphthylamine	NC1CCCC2=CC=CC=C12	1335.1	Standard non polar	33892256
1,2,3,4-Tetrahydro-1-naphthylamine	NC1CCCC2=CC=CC=C12	1353.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1,2,3,4-Tetrahydro-1-naphthylamine,1TMS,isomer #1	C[Si](C)(C)NC1CCCC2=CC=CC=C21	1545.1	Semi standard non polar	33892256
1,2,3,4-Tetrahydro-1-naphthylamine,1TMS,isomer #1	C[Si](C)(C)NC1CCCC2=CC=CC=C21	1482.1	Standard non polar	33892256
1,2,3,4-Tetrahydro-1-naphthylamine,1TMS,isomer #1	C[Si](C)(C)NC1CCCC2=CC=CC=C21	1886.7	Standard polar	33892256
1,2,3,4-Tetrahydro-1-naphthylamine,2TMS,isomer #1	C[Si](C)(C)N(C1CCCC2=CC=CC=C21)[Si](C)(C)C	1711.6	Semi standard non polar	33892256
1,2,3,4-Tetrahydro-1-naphthylamine,2TMS,isomer #1	C[Si](C)(C)N(C1CCCC2=CC=CC=C21)[Si](C)(C)C	1698.5	Standard non polar	33892256
1,2,3,4-Tetrahydro-1-naphthylamine,2TMS,isomer #1	C[Si](C)(C)N(C1CCCC2=CC=CC=C21)[Si](C)(C)C	1946.8	Standard polar	33892256
1,2,3,4-Tetrahydro-1-naphthylamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1CCCC2=CC=CC=C21	1788.2	Semi standard non polar	33892256
1,2,3,4-Tetrahydro-1-naphthylamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1CCCC2=CC=CC=C21	1805.7	Standard non polar	33892256
1,2,3,4-Tetrahydro-1-naphthylamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1CCCC2=CC=CC=C21	2073.0	Standard polar	33892256
1,2,3,4-Tetrahydro-1-naphthylamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1CCCC2=CC=CC=C21)[Si](C)(C)C(C)(C)C	2125.3	Semi standard non polar	33892256
1,2,3,4-Tetrahydro-1-naphthylamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1CCCC2=CC=CC=C21)[Si](C)(C)C(C)(C)C	2259.0	Standard non polar	33892256
1,2,3,4-Tetrahydro-1-naphthylamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1CCCC2=CC=CC=C21)[Si](C)(C)C(C)(C)C	2158.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2,3,4-Tetrahydro-1-naphthylamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0159-0900000000-f245c26fcacd2b1ac073	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2,3,4-Tetrahydro-1-naphthylamine 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 - 1,2,3,4-Tetrahydro-1-naphthylamine 10V, Positive-QTOF	splash10-000t-0900000000-60c9022b28d3bef74c09	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-1-naphthylamine 20V, Positive-QTOF	splash10-000t-1900000000-99423ba0eef5daa393dd	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-1-naphthylamine 40V, Positive-QTOF	splash10-0f76-8900000000-d047f16e4d0c4186cad0	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-1-naphthylamine 10V, Negative-QTOF	splash10-0002-0900000000-f8c54039eb487f81b8e1	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-1-naphthylamine 20V, Negative-QTOF	splash10-0002-0900000000-dbf82fd7ff6dcf6ca5e0	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-1-naphthylamine 40V, Negative-QTOF	splash10-0007-3900000000-6a9b27034ba02611cf59	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-1-naphthylamine 10V, Positive-QTOF	splash10-000t-0900000000-be4c2492a269bb46b9b7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-1-naphthylamine 20V, Positive-QTOF	splash10-001l-3900000000-d232fda4b7f3baba270c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-1-naphthylamine 40V, Positive-QTOF	splash10-0006-9200000000-25a51bfbbbe24b9c3352	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-1-naphthylamine 10V, Negative-QTOF	splash10-002b-0900000000-bfe1613970ed92638afc	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-1-naphthylamine 20V, Negative-QTOF	splash10-0002-0900000000-55cfbffe91aa3170d21b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-1-naphthylamine 40V, Negative-QTOF	splash10-002f-9800000000-13c721fe89bb64e46df0	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

18066

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 1,2,3,4-Tetrahydro-1-naphthylamine (HMDB0244116)

MOL for HMDB0244116 (1,2,3,4-Tetrahydro-1-naphthylamine)

3D MOL for HMDB0244116 (1,2,3,4-Tetrahydro-1-naphthylamine)

3D SDF for HMDB0244116 (1,2,3,4-Tetrahydro-1-naphthylamine)

3D-SDF for HMDB0244116 (1,2,3,4-Tetrahydro-1-naphthylamine)

PDB for HMDB0244116 (1,2,3,4-Tetrahydro-1-naphthylamine)

3D PDB for HMDB0244116 (1,2,3,4-Tetrahydro-1-naphthylamine)

SMILES for HMDB0244116 (1,2,3,4-Tetrahydro-1-naphthylamine)

INCHI for HMDB0244116 (1,2,3,4-Tetrahydro-1-naphthylamine)

Structure for HMDB0244116 (1,2,3,4-Tetrahydro-1-naphthylamine)

3D Structure for HMDB0244116 (1,2,3,4-Tetrahydro-1-naphthylamine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra