Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:26:43 UTC

Update Date

2021-09-26 22:55:29 UTC

HMDB ID

HMDB0246424

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-Fluoroamphetamine

Description

1-(4-fluorophenyl)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. 1-(4-fluorophenyl)propan-2-amine is a very strong basic compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-fluoroamphetamine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-Fluoroamphetamine 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
2-Fluoroamphetamine	MeSH
4-Fluoroamphetamine	MeSH
4-Fluoroamphetamine hydrochloride	MeSH
4-Fluoroamphetamine hydrochloride, (+-)-isomer	MeSH
4-Fluoroamphetamine, (+-)-isomer	MeSH
4-Fluoroamphetamine, (R)-isomer	MeSH
Para-fluoroamphetamine	MeSH

Chemical Formula

C₉H₁₂FN

Average Molecular Weight

153.2

Monoisotopic Molecular Weight

153.095377553

IUPAC Name

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

Traditional Name

4-fluoroamphetamine

CAS Registry Number

Not Available

SMILES

CC(N)CC1=CC=C(F)C=C1

InChI Identifier

InChI=1S/C9H12FN/c1-7(11)6-8-2-4-9(10)5-3-8/h2-5,7H,6,11H2,1H3

InChI Key

DGXWNDGLEOIEGT-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
Aralkylamine
Fluorobenzene
Halobenzene
Aryl fluoride
Aryl halide
Amine
Organofluoride
Organohalogen compound
Primary aliphatic amine
Organonitrogen compound
Primary amine
Hydrocarbon derivative
Organopnictogen compound
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)

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	1.95	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Basic)	10.02	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	2	ChemAxon
Refractivity	43.92 m³·mol⁻¹	ChemAxon
Polarizability	16.29 Å³	ChemAxon
Number of Rings	1	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+H]+	139.177	30932474
DeepCCS	[M-H]-	135.518	30932474
DeepCCS	[M-2H]-	173.106	30932474
DeepCCS	[M+Na]+	148.644	30932474
AllCCS	[M+H]+	133.4	32859911
AllCCS	[M+H-H2O]+	128.9	32859911
AllCCS	[M+NH4]+	137.6	32859911
AllCCS	[M+Na]+	138.8	32859911
AllCCS	[M-H]-	133.6	32859911
AllCCS	[M+Na-2H]-	135.0	32859911
AllCCS	[M+HCOO]-	136.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Fluoroamphetamine	CC(N)CC1=CC=C(F)C=C1	1969.3	Standard polar	33892256
4-Fluoroamphetamine	CC(N)CC1=CC=C(F)C=C1	1105.1	Standard non polar	33892256
4-Fluoroamphetamine	CC(N)CC1=CC=C(F)C=C1	1149.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Fluoroamphetamine,1TMS,isomer #1	CC(CC1=CC=C(F)C=C1)N[Si](C)(C)C	1312.1	Semi standard non polar	33892256
4-Fluoroamphetamine,1TMS,isomer #1	CC(CC1=CC=C(F)C=C1)N[Si](C)(C)C	1387.1	Standard non polar	33892256
4-Fluoroamphetamine,1TMS,isomer #1	CC(CC1=CC=C(F)C=C1)N[Si](C)(C)C	1533.2	Standard polar	33892256
4-Fluoroamphetamine,2TMS,isomer #1	CC(CC1=CC=C(F)C=C1)N([Si](C)(C)C)[Si](C)(C)C	1536.2	Semi standard non polar	33892256
4-Fluoroamphetamine,2TMS,isomer #1	CC(CC1=CC=C(F)C=C1)N([Si](C)(C)C)[Si](C)(C)C	1575.1	Standard non polar	33892256
4-Fluoroamphetamine,2TMS,isomer #1	CC(CC1=CC=C(F)C=C1)N([Si](C)(C)C)[Si](C)(C)C	1562.0	Standard polar	33892256
4-Fluoroamphetamine,1TBDMS,isomer #1	CC(CC1=CC=C(F)C=C1)N[Si](C)(C)C(C)(C)C	1550.3	Semi standard non polar	33892256
4-Fluoroamphetamine,1TBDMS,isomer #1	CC(CC1=CC=C(F)C=C1)N[Si](C)(C)C(C)(C)C	1591.0	Standard non polar	33892256
4-Fluoroamphetamine,1TBDMS,isomer #1	CC(CC1=CC=C(F)C=C1)N[Si](C)(C)C(C)(C)C	1689.2	Standard polar	33892256
4-Fluoroamphetamine,2TBDMS,isomer #1	CC(CC1=CC=C(F)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1987.3	Semi standard non polar	33892256
4-Fluoroamphetamine,2TBDMS,isomer #1	CC(CC1=CC=C(F)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1978.5	Standard non polar	33892256
4-Fluoroamphetamine,2TBDMS,isomer #1	CC(CC1=CC=C(F)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1805.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Fluoroamphetamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9500000000-b5ae6d378d8d935e5563	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Fluoroamphetamine 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-Fluoroamphetamine 10V, Positive-QTOF	splash10-0udr-0900000000-5532fb60d9887bf7a1cb	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Fluoroamphetamine 20V, Positive-QTOF	splash10-0f79-0900000000-bf9f79dbfe65a1358fda	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Fluoroamphetamine 40V, Positive-QTOF	splash10-05tu-7900000000-618d3c702c18f2a59c25	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Fluoroamphetamine 10V, Negative-QTOF	splash10-0udi-0900000000-eff9bc0e26eb98029549	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Fluoroamphetamine 20V, Negative-QTOF	splash10-0udi-0900000000-e290c273cfbacec3330c	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Fluoroamphetamine 40V, Negative-QTOF	splash10-00kr-1900000000-a3e1718286f712891417	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Fluoroamphetamine 10V, Positive-QTOF	splash10-0f79-0900000000-f416dc41b585d5a764bb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Fluoroamphetamine 20V, Positive-QTOF	splash10-0a4i-0900000000-ee7248d1762826e37dd0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Fluoroamphetamine 40V, Positive-QTOF	splash10-0a4i-5900000000-60585ac5c63cba66debb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Fluoroamphetamine 10V, Negative-QTOF	splash10-0zfr-0900000000-b7a93da74a44b553c332	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Fluoroamphetamine 20V, Negative-QTOF	splash10-0pbi-0900000000-b03ede44acc846ba6bc1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Fluoroamphetamine 40V, Negative-QTOF	splash10-0a4i-6900000000-b743f40a6a9b69fc8455	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

9986

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-Fluoroamphetamine (HMDB0246424)

MOL for HMDB0246424 (4-Fluoroamphetamine)

3D MOL for HMDB0246424 (4-Fluoroamphetamine)

3D SDF for HMDB0246424 (4-Fluoroamphetamine)

3D-SDF for HMDB0246424 (4-Fluoroamphetamine)

PDB for HMDB0246424 (4-Fluoroamphetamine)

3D PDB for HMDB0246424 (4-Fluoroamphetamine)

SMILES for HMDB0246424 (4-Fluoroamphetamine)

INCHI for HMDB0246424 (4-Fluoroamphetamine)

Structure for HMDB0246424 (4-Fluoroamphetamine)

3D Structure for HMDB0246424 (4-Fluoroamphetamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra