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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 18:58:14 UTC

Update Date

2023-02-21 17:30:14 UTC

HMDB ID

HMDB0060767

Secondary Accession Numbers

HMDB60767

Metabolite Identification

Common Name

4-Hydroxymethamphetamine

Description

4-Hydroxymethamphetamine 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

HEADER    PROTEIN                                 04-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUL-13         0                                  
HETATM    1  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       0.000  -4.620   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2   11                                                            
CONECT    3    5    9                                                       
CONECT    4    6    9                                                       
CONECT    5    3   10                                                       
CONECT    6    4   10                                                       
CONECT    7    8    9                                                       
CONECT    8    1    7   11                                                  
CONECT    9    3    4    7                                                  
CONECT   10    5    6   12                                                  
CONECT   11    2    8                                                       
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

COMPND    HMDB0060767
HETATM    1  C1  UNL     1      -2.571   0.328   1.845  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.564   0.575   0.862  1.00  0.00           N  
HETATM    3  C2  UNL     1      -1.557  -0.418  -0.211  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.900  -0.301  -0.900  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.441  -0.052  -1.166  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.880  -0.041  -0.530  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.657  -1.178  -0.496  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.909  -1.198   0.098  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.400  -0.033   0.681  1.00  0.00           C  
HETATM   10  O1  UNL     1       4.665  -0.102   1.267  1.00  0.00           O  
HETATM   11  C9  UNL     1       2.639   1.109   0.657  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.392   1.090   0.054  1.00  0.00           C  
HETATM   13  H1  UNL     1      -2.275   0.909   2.766  1.00  0.00           H  
HETATM   14  H2  UNL     1      -3.574   0.711   1.576  1.00  0.00           H  
HETATM   15  H3  UNL     1      -2.689  -0.743   2.110  1.00  0.00           H  
HETATM   16  H4  UNL     1      -1.790   1.491   0.395  1.00  0.00           H  
HETATM   17  H5  UNL     1      -1.439  -1.431   0.203  1.00  0.00           H  
HETATM   18  H6  UNL     1      -2.722   0.015  -1.946  1.00  0.00           H  
HETATM   19  H7  UNL     1      -3.434  -1.271  -0.934  1.00  0.00           H  
HETATM   20  H8  UNL     1      -3.553   0.473  -0.451  1.00  0.00           H  
HETATM   21  H9  UNL     1      -0.709   0.941  -1.623  1.00  0.00           H  
HETATM   22  H10 UNL     1      -0.477  -0.778  -2.015  1.00  0.00           H  
HETATM   23  H11 UNL     1       1.319  -2.109  -0.936  1.00  0.00           H  
HETATM   24  H12 UNL     1       3.500  -2.084   0.116  1.00  0.00           H  
HETATM   25  H13 UNL     1       5.472   0.111   0.674  1.00  0.00           H  
HETATM   26  H14 UNL     1       3.055   1.995   1.121  1.00  0.00           H  
HETATM   27  H15 UNL     1       0.806   1.991   0.042  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3   16
CONECT    3    4    5   17
CONECT    4   18   19   20
CONECT    5    6   21   22
CONECT    6    7    7   12
CONECT    7    8   23
CONECT    8    9    9   24
CONECT    9   10   11
CONECT   10   25
CONECT   11   12   12   26
CONECT   12   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Hydroxymethamphetamine	MeSH
Pholedrin-longo-isis	MeSH, HMDB
Pholedrin liquidum	MeSH, HMDB
Pholedrine sulfate (1:1)	MeSH, HMDB
Pholedrine, sulfate (1:1), (+-)-isomer	MeSH, HMDB
Pholedrine, sulfate (2:1), (+-)-isomer	MeSH, HMDB
Veritol	MeSH, HMDB
4-Hydroxy-N-methylamphetamine	MeSH, HMDB
P-Hydroxymethamphetamine	MeSH, HMDB
Pholedrine sulfate (2:1)	MeSH, HMDB
Pulsotyl	MeSH, HMDB

Chemical Formula

C₁₀H₁₅NO

Average Molecular Weight

165.2322

Monoisotopic Molecular Weight

165.115364107

IUPAC Name

4-[2-(methylamino)propyl]phenol

Traditional Name

pholedrine sulfate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

SBUQZKJEOOQSBV-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
Secondary amine
Secondary aliphatic amine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
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: HMDB0060767)

Organ

Kidney (HMDB: HMDB0060767)
Liver (HMDB: HMDB0060767)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060767)

Cellular substructure

Cytoplasm (HMDB: HMDB0060767)

Source

Endogenous

Endogenous (HMDB: HMDB0060767)

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	1.44 g/L	ALOGPS
logP	1.12	ALOGPS
logP	1.33	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	9.86	ChemAxon
pKa (Strongest Basic)	10.58	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	32.26 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	50.46 m³·mol⁻¹	ChemAxon
Polarizability	19.15 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
DarkChem	[M+H]+	138.488	31661259
DarkChem	[M-H]-	136.942	31661259
DeepCCS	[M+H]+	140.89	30932474
DeepCCS	[M-H]-	137.062	30932474
DeepCCS	[M-2H]-	174.755	30932474
DeepCCS	[M+Na]+	150.293	30932474
AllCCS	[M+H]+	137.5	32859911
AllCCS	[M+H-H2O]+	133.2	32859911
AllCCS	[M+NH4]+	141.6	32859911
AllCCS	[M+Na]+	142.8	32859911
AllCCS	[M-H]-	139.8	32859911
AllCCS	[M+Na-2H]-	141.1	32859911
AllCCS	[M+HCOO]-	142.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxymethamphetamine	CNC(C)CC1=CC=C(O)C=C1	2440.3	Standard polar	33892256
4-Hydroxymethamphetamine	CNC(C)CC1=CC=C(O)C=C1	1489.5	Standard non polar	33892256
4-Hydroxymethamphetamine	CNC(C)CC1=CC=C(O)C=C1	1523.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxymethamphetamine,1TMS,isomer #1	CNC(C)CC1=CC=C(O[Si](C)(C)C)C=C1	1524.8	Semi standard non polar	33892256
4-Hydroxymethamphetamine,1TMS,isomer #2	CC(CC1=CC=C(O)C=C1)N(C)[Si](C)(C)C	1686.2	Semi standard non polar	33892256
4-Hydroxymethamphetamine,2TMS,isomer #1	CC(CC1=CC=C(O[Si](C)(C)C)C=C1)N(C)[Si](C)(C)C	1728.6	Semi standard non polar	33892256
4-Hydroxymethamphetamine,2TMS,isomer #1	CC(CC1=CC=C(O[Si](C)(C)C)C=C1)N(C)[Si](C)(C)C	1695.5	Standard non polar	33892256
4-Hydroxymethamphetamine,2TMS,isomer #1	CC(CC1=CC=C(O[Si](C)(C)C)C=C1)N(C)[Si](C)(C)C	1767.8	Standard polar	33892256
4-Hydroxymethamphetamine,1TBDMS,isomer #1	CNC(C)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	1783.0	Semi standard non polar	33892256
4-Hydroxymethamphetamine,1TBDMS,isomer #2	CC(CC1=CC=C(O)C=C1)N(C)[Si](C)(C)C(C)(C)C	1911.9	Semi standard non polar	33892256
4-Hydroxymethamphetamine,2TBDMS,isomer #1	CC(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N(C)[Si](C)(C)C(C)(C)C	2223.0	Semi standard non polar	33892256
4-Hydroxymethamphetamine,2TBDMS,isomer #1	CC(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N(C)[Si](C)(C)C(C)(C)C	2159.4	Standard non polar	33892256
4-Hydroxymethamphetamine,2TBDMS,isomer #1	CC(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N(C)[Si](C)(C)C(C)(C)C	2052.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxymethamphetamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9200000000-aa543cec4c62e49e3a10	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxymethamphetamine GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-9220000000-88f9572807ab2592aec3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxymethamphetamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxymethamphetamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxymethamphetamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxymethamphetamine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxymethamphetamine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxymethamphetamine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	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-Hydroxymethamphetamine 10V, Positive-QTOF	splash10-014i-0900000000-12d562392b32df6e6d47	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxymethamphetamine 20V, Positive-QTOF	splash10-014r-2900000000-1ba90d221eae21d71931	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxymethamphetamine 40V, Positive-QTOF	splash10-0aor-9400000000-03e2b554733bbe0d58d7	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxymethamphetamine 10V, Negative-QTOF	splash10-03di-0900000000-56e2c9c0b6c095935e83	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxymethamphetamine 20V, Negative-QTOF	splash10-03di-0900000000-2a9fa588ebc52ed93375	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxymethamphetamine 40V, Negative-QTOF	splash10-0a4i-9800000000-0d6a3777120f6f83ba52	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxymethamphetamine 10V, Positive-QTOF	splash10-014i-0900000000-b87e49223bf28f5d7b51	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxymethamphetamine 20V, Positive-QTOF	splash10-0a4i-4900000000-1ee2a1a917fc6ab5fc0c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxymethamphetamine 40V, Positive-QTOF	splash10-004l-9200000000-cfce27a45900b9663c4e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxymethamphetamine 10V, Negative-QTOF	splash10-03di-0900000000-5a67776f4d9f6897ce74	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxymethamphetamine 20V, Negative-QTOF	splash10-03e9-0900000000-e799217bdcf4792f9100	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxymethamphetamine 40V, Negative-QTOF	splash10-066u-6900000000-7f72cd1b15aa20abbe04	2021-10-12	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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4494

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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-Hydroxymethamphetamine (HMDB0060767)

MOL for HMDB0060767 (4-Hydroxymethamphetamine)

3D MOL for HMDB0060767 (4-Hydroxymethamphetamine)

3D SDF for HMDB0060767 (4-Hydroxymethamphetamine)

3D-SDF for HMDB0060767 (4-Hydroxymethamphetamine)

PDB for HMDB0060767 (4-Hydroxymethamphetamine)

3D PDB for HMDB0060767 (4-Hydroxymethamphetamine)

SMILES for HMDB0060767 (4-Hydroxymethamphetamine)

INCHI for HMDB0060767 (4-Hydroxymethamphetamine)

Structure for HMDB0060767 (4-Hydroxymethamphetamine)

3D Structure for HMDB0060767 (4-Hydroxymethamphetamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra