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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 18:58:09 UTC

Update Date

2023-02-21 17:30:14 UTC

HMDB ID

HMDB0060765

Secondary Accession Numbers

HMDB60765

Metabolite Identification

Common Name

4-Hydroxyamphetamine

Description

4-Hydroxyamphetamine is a metabolite of methamphetamine. Methamphetamine, also known as methamfetamine, meth, N-methylamphetamine, methylamphetamine, and desoxyephedrine, is a psychostimulant of the phenethylamine and amphetamine class of psychoactive drugs. Methamphetamine increases alertness, concentration, energy, and in high doses, can induce euphoria, enhance self-esteem and increase libido. (Wikipedia )

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
HYDROXYAMFETAMINE	HMDB
Hydrobromide, hydroxyamphetamine	HMDB
Hydroxyamphetamin	HMDB
Hydroxyamphetamine hydrobromide	HMDB
Norpholedrin	HMDB
Oxyamphetamine	HMDB
p-Hydroxyamphetamine	HMDB
Para hydroxyamphetamine	HMDB
Hydroxyphenylisopropylamine	HMDB
Paredrine	HMDB
p Hydroxyamphetamine	HMDB
Para-hydroxyamphetamine	HMDB
Methyltyramine	HMDB
Hydroxyamphetamine	HMDB

Chemical Formula

C₉H₁₃NO

Average Molecular Weight

151.2056

Monoisotopic Molecular Weight

151.099714043

IUPAC Name

4-(2-aminopropyl)phenol

Traditional Name

p-hydroxyamphetamine

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C9H13NO/c1-7(10)6-8-2-4-9(11)5-3-8/h2-5,7,11H,6,10H2,1H3

InChI Key

GIKNHHRFLCDOEU-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
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Phenol
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Amine
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 (HMDB: HMDB0060765)

Organ

Kidney (HMDB: HMDB0060765)
Liver (HMDB: HMDB0060765)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060765)

Cellular substructure

Cytoplasm (HMDB: HMDB0060765)

Source

Endogenous

Endogenous (HMDB: HMDB0060765)

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
Water Solubility	3.13 g/L	ALOGPS
logP	0.58	ALOGPS
logP	1	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	10.48	ChemAxon
pKa (Strongest Basic)	9.8	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	46.25 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	45.69 m³·mol⁻¹	ChemAxon
Polarizability	17.17 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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
DarkChem	[M+H]+	133.604	31661259
DarkChem	[M-H]-	131.086	31661259
DeepCCS	[M+H]+	137.472	30932474
DeepCCS	[M-H]-	133.749	30932474
DeepCCS	[M-2H]-	171.411	30932474
DeepCCS	[M+Na]+	146.949	30932474
AllCCS	[M+H]+	133.7	32859911
AllCCS	[M+H-H2O]+	129.2	32859911
AllCCS	[M+NH4]+	137.9	32859911
AllCCS	[M+Na]+	139.1	32859911
AllCCS	[M-H]-	134.5	32859911
AllCCS	[M+Na-2H]-	136.0	32859911
AllCCS	[M+HCOO]-	137.6	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. Predicted by Afia on May 17, 2022.	1.76 minutes	32390414
Predicted by Siyang on May 30, 2022	9.3779 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.3 minutes	32390414

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxyamphetamine	CC(N)CC1=CC=C(O)C=C1	2607.9	Standard polar	33892256
4-Hydroxyamphetamine	CC(N)CC1=CC=C(O)C=C1	1410.6	Standard non polar	33892256
4-Hydroxyamphetamine	CC(N)CC1=CC=C(O)C=C1	1475.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxyamphetamine,1TMS,isomer #1	CC(N)CC1=CC=C(O[Si](C)(C)C)C=C1	1500.5	Semi standard non polar	33892256
4-Hydroxyamphetamine,1TMS,isomer #2	CC(CC1=CC=C(O)C=C1)N[Si](C)(C)C	1665.3	Semi standard non polar	33892256
4-Hydroxyamphetamine,2TMS,isomer #1	CC(CC1=CC=C(O[Si](C)(C)C)C=C1)N[Si](C)(C)C	1629.4	Semi standard non polar	33892256
4-Hydroxyamphetamine,2TMS,isomer #1	CC(CC1=CC=C(O[Si](C)(C)C)C=C1)N[Si](C)(C)C	1629.4	Standard non polar	33892256
4-Hydroxyamphetamine,2TMS,isomer #1	CC(CC1=CC=C(O[Si](C)(C)C)C=C1)N[Si](C)(C)C	1768.6	Standard polar	33892256
4-Hydroxyamphetamine,2TMS,isomer #2	CC(CC1=CC=C(O)C=C1)N([Si](C)(C)C)[Si](C)(C)C	1817.4	Semi standard non polar	33892256
4-Hydroxyamphetamine,2TMS,isomer #2	CC(CC1=CC=C(O)C=C1)N([Si](C)(C)C)[Si](C)(C)C	1876.1	Standard non polar	33892256
4-Hydroxyamphetamine,2TMS,isomer #2	CC(CC1=CC=C(O)C=C1)N([Si](C)(C)C)[Si](C)(C)C	1972.4	Standard polar	33892256
4-Hydroxyamphetamine,3TMS,isomer #1	CC(CC1=CC=C(O[Si](C)(C)C)C=C1)N([Si](C)(C)C)[Si](C)(C)C	1867.0	Semi standard non polar	33892256
4-Hydroxyamphetamine,3TMS,isomer #1	CC(CC1=CC=C(O[Si](C)(C)C)C=C1)N([Si](C)(C)C)[Si](C)(C)C	1791.0	Standard non polar	33892256
4-Hydroxyamphetamine,3TMS,isomer #1	CC(CC1=CC=C(O[Si](C)(C)C)C=C1)N([Si](C)(C)C)[Si](C)(C)C	1786.5	Standard polar	33892256
4-Hydroxyamphetamine,1TBDMS,isomer #1	CC(N)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	1723.5	Semi standard non polar	33892256
4-Hydroxyamphetamine,1TBDMS,isomer #2	CC(CC1=CC=C(O)C=C1)N[Si](C)(C)C(C)(C)C	1877.3	Semi standard non polar	33892256
4-Hydroxyamphetamine,2TBDMS,isomer #1	CC(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N[Si](C)(C)C(C)(C)C	2127.5	Semi standard non polar	33892256
4-Hydroxyamphetamine,2TBDMS,isomer #1	CC(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N[Si](C)(C)C(C)(C)C	2086.7	Standard non polar	33892256
4-Hydroxyamphetamine,2TBDMS,isomer #1	CC(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N[Si](C)(C)C(C)(C)C	2058.7	Standard polar	33892256
4-Hydroxyamphetamine,2TBDMS,isomer #2	CC(CC1=CC=C(O)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2250.8	Semi standard non polar	33892256
4-Hydroxyamphetamine,2TBDMS,isomer #2	CC(CC1=CC=C(O)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2315.1	Standard non polar	33892256
4-Hydroxyamphetamine,2TBDMS,isomer #2	CC(CC1=CC=C(O)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2135.8	Standard polar	33892256
4-Hydroxyamphetamine,3TBDMS,isomer #1	CC(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2567.9	Semi standard non polar	33892256
4-Hydroxyamphetamine,3TBDMS,isomer #1	CC(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2414.1	Standard non polar	33892256
4-Hydroxyamphetamine,3TBDMS,isomer #1	CC(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2132.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyamphetamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9800000000-be314d40e4f3eec02c64	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyamphetamine GC-MS (1 TMS) - 70eV, Positive	splash10-0006-9520000000-27b26e501065c88f2e44	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyamphetamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyamphetamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyamphetamine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyamphetamine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyamphetamine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	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-Hydroxyamphetamine 10V, Positive-QTOF	splash10-0udr-0900000000-ce983c3333043fa75138	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyamphetamine 20V, Positive-QTOF	splash10-0f79-1900000000-a25d07320a871a151c90	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyamphetamine 40V, Positive-QTOF	splash10-0670-8900000000-01eef85998096c783c89	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyamphetamine 10V, Negative-QTOF	splash10-0udi-0900000000-9127f6d37951111e3ca5	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyamphetamine 20V, Negative-QTOF	splash10-0udi-0900000000-63b9d3f1a2d2019491a4	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyamphetamine 40V, Negative-QTOF	splash10-001i-3900000000-82c27ad632334acd666f	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyamphetamine 10V, Negative-QTOF	splash10-0zfr-0900000000-82f62a52cf320914dd1e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyamphetamine 20V, Negative-QTOF	splash10-0pb9-0900000000-a9f0104927f0505bdb7e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyamphetamine 40V, Negative-QTOF	splash10-0006-9400000000-c422ecbb2ca5cb2ab89d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyamphetamine 10V, Positive-QTOF	splash10-0f79-0900000000-1559527532c5eafbb7ee	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyamphetamine 20V, Positive-QTOF	splash10-0a4i-3900000000-a43fa60f8dfe5ea4df1f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyamphetamine 40V, Positive-QTOF	splash10-004i-9100000000-5033c3c68adccf158b05	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB09352

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3525

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

4-Hydroxyamphetamine

METLIN ID

Not Available

PubChem Compound

3651

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

Not Available

Showing metabocard for 4-Hydroxyamphetamine (HMDB0060765)

MOL for HMDB0060765 (4-Hydroxyamphetamine)

3D MOL for HMDB0060765 (4-Hydroxyamphetamine)

3D SDF for HMDB0060765 (4-Hydroxyamphetamine)

3D-SDF for HMDB0060765 (4-Hydroxyamphetamine)

PDB for HMDB0060765 (4-Hydroxyamphetamine)

3D PDB for HMDB0060765 (4-Hydroxyamphetamine)

SMILES for HMDB0060765 (4-Hydroxyamphetamine)

INCHI for HMDB0060765 (4-Hydroxyamphetamine)

Structure for HMDB0060765 (4-Hydroxyamphetamine)

3D Structure for HMDB0060765 (4-Hydroxyamphetamine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra