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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:17 UTC

HMDB ID

HMDB0000898

Secondary Accession Numbers

HMDB0000976
HMDB00898
HMDB00976

Metabolite Identification

Common Name

1-Methylhistamine

Description

1-Methylhistamine, also known as H137, belongs to the class of organic compounds known as 2-arylethylamines. These are primary amines that have the general formula RCCNH2, where R is an organic group. 1-Methylhistamine exists in all living organisms, ranging from bacteria to humans. Within humans, 1-methylhistamine participates in a number of enzymatic reactions. In particular, S-adenosylhomocysteine and 1-methylhistamine can be biosynthesized from S-adenosylmethionine and histamine; which is mediated by the enzyme histamine N-methyltransferase. In addition, 1-methylhistamine can be converted into methylimidazole acetaldehyde through its interaction with the enzyme amine oxidase [flavin-containing] a. In humans, 1-methylhistamine is involved in histidine metabolism. 1-Methylhistamine is a potentially toxic compound.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-Methyl-1H-imidazole-4-ethanamine	ChEBI
1-Methyl-4-(2-aminoethyl)imidazole	ChEBI
3-Methylhistamine	ChEBI
4-(1-Aminoethyl)-1-methyl-1H-imidazole	ChEBI
Methylhistamine	ChEBI
N-Methylhistamine	ChEBI
N(1)-Methylhistamine	ChEBI
Ntau-methylhistamine	ChEBI
tele-Methylhistamine	ChEBI
tele-Methylhistamine dihydrochloride	HMDB
1-Methyl-4-(beta-aminoethyl)imidazole	HMDB
1,4-Methylhistamine	HMDB
N-tele Methylhistamine	HMDB
1-Methyl-4-(b-aminoethyl)imidazole	HMDB
1-Methyl-4-histamine	HMDB
2-(1-Methyl-1H-imidazol-4-yl)ethanamine	HMDB
2-(1-Methyl-1H-imidazol-4-yl)ethylamine	HMDB
4-(2-Aminoethyl)-1-methyl-imidazole	HMDB
4-(2-Aminoethyl)-1-methylimidazole	HMDB
H137	HMDB
N( 1)-Methylhistamine	HMDB
N(T)-Methylhistamine	HMDB
N-tele-Methylhistamine	HMDB
N-Telle-methylhistamine	HMDB
N1-Methylhistamine	HMDB
NT-Methylhistamine	HMDB

Chemical Formula

C₆H₁₁N₃

Average Molecular Weight

125.1716

Monoisotopic Molecular Weight

125.095297367

IUPAC Name

2-(1-methyl-1H-imidazol-4-yl)ethan-1-amine

Traditional Name

methylhistamine

CAS Registry Number

501-75-7

SMILES

CN1C=NC(CCN)=C1

InChI Identifier

InChI=1S/C6H11N3/c1-9-4-6(2-3-7)8-5-9/h4-5H,2-3,7H2,1H3

InChI Key

FHQDWPCFSJMNCT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylethylamines. These are primary amines that have the general formula RCCNH2, where R is an organic group.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

2-arylethylamines

Alternative Parents

Substituents

2-arylethylamine
Aralkylamine
N-substituted imidazole
Heteroaromatic compound
Imidazole
Azole
Azacycle
Organoheterocyclic compound
Organopnictogen compound
Hydrocarbon derivative
Primary aliphatic amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

imidazoles (CHEBI:29009 )
primary amino compound (CHEBI:29009 )

Ontology

Physiological effect

Health effect

Nervous system disorder

Central nervous system disorder

Psychiatric disorder

Schizophrenia (HMDB: HMDB0000898)

Circulatory system disorder

Blood and lymphatic system disorder

Leukocytic disorder

Mastocytosis (HMDB: HMDB0000898)

Skin and subcutaneous tissue disorder

Skin disorder

Dermal fibroproliferative disorder (HMDB: HMDB0000898)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 9234842)
Saliva (HMDB: HMDB0000898)
Cerebrospinal Fluid (CSF) (PMID: 7886118)
Cerebrospinal fluid (HMDB: HMDB0000898)

Cell

Mast cell (HMDB: HMDB0000898)
Mast cell (HMDB: HMDB0000898)

Tissue

Connective tissue

Bone marrow (HMDB: HMDB0000898)
Bone marrow (HMDB: HMDB0000898)

Organ

Brain (HMDB: HMDB0000898)

Excreta

Biofluid or Excreta

Urine (PMID: 10027644)
Feces (PMID: 27609529)

Cellular substructure

Cytoplasm (HMDB: HMDB0000898)
Extracellular (HMDB: HMDB0000898)

Source

Endogenous

Endogenous (HMDB: HMDB0000898)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Histidine Metabolism (HMDB: HMDB0000898)
Histidine Metabolism (HMDB: HMDB0000898)

Disease pathway

Histidinemia (HMDB: HMDB0000898)

Role

Biological role

Human metabolite (HMDB: HMDB0000898)

Industrial application

Pharmaceutical industry

Biomarker

Mastocytosis (MarkerDB: MDB00000278)
Dermal fibroproliferative disorder (MarkerDB: MDB00000278)

Physical Properties

State

Solid

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

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Baker	122.555	30932474
[M+H]+	MetCCS_train_pos	121.302	30932474
[M+H]+	Not Available	121.9	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000535

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.12 g/L	ALOGPS
logP	-0.57	ALOGPS
logP	-0.48	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Basic)	9.57	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	43.84 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	36.56 m³·mol⁻¹	ChemAxon
Polarizability	14.24 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]+	126.156	31661259
DarkChem	[M+H]+	126.156	31661259
DarkChem	[M-H]-	123.869	31661259
DarkChem	[M-H]-	123.869	31661259
AllCCS	[M+H]+	127.188	32859911
AllCCS	[M-H]-	127.172	32859911
DeepCCS	[M+H]+	122.348	30932474
DeepCCS	[M-H]-	119.101	30932474
DeepCCS	[M-2H]-	155.745	30932474
DeepCCS	[M+Na]+	130.917	30932474
AllCCS	[M+H]+	127.2	32859911
AllCCS	[M+H-H2O]+	122.5	32859911
AllCCS	[M+NH4]+	131.5	32859911
AllCCS	[M+Na]+	132.8	32859911
AllCCS	[M-H]-	127.2	32859911
AllCCS	[M+Na-2H]-	129.4	32859911
AllCCS	[M+HCOO]-	131.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-Methylhistamine	CN1C=NC(CCN)=C1	2150.0	Standard polar	33892256
1-Methylhistamine	CN1C=NC(CCN)=C1	1375.0	Standard non polar	33892256
1-Methylhistamine	CN1C=NC(CCN)=C1	1277.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1-Methylhistamine,1TMS,isomer #1	CN1C=NC(CCN[Si](C)(C)C)=C1	1513.1	Semi standard non polar	33892256
1-Methylhistamine,1TMS,isomer #1	CN1C=NC(CCN[Si](C)(C)C)=C1	1559.5	Standard non polar	33892256
1-Methylhistamine,1TMS,isomer #1	CN1C=NC(CCN[Si](C)(C)C)=C1	1930.0	Standard polar	33892256
1-Methylhistamine,2TMS,isomer #1	CN1C=NC(CCN([Si](C)(C)C)[Si](C)(C)C)=C1	1793.8	Semi standard non polar	33892256
1-Methylhistamine,2TMS,isomer #1	CN1C=NC(CCN([Si](C)(C)C)[Si](C)(C)C)=C1	1764.3	Standard non polar	33892256
1-Methylhistamine,2TMS,isomer #1	CN1C=NC(CCN([Si](C)(C)C)[Si](C)(C)C)=C1	1892.4	Standard polar	33892256
1-Methylhistamine,1TBDMS,isomer #1	CN1C=NC(CCN[Si](C)(C)C(C)(C)C)=C1	1743.8	Semi standard non polar	33892256
1-Methylhistamine,1TBDMS,isomer #1	CN1C=NC(CCN[Si](C)(C)C(C)(C)C)=C1	1791.7	Standard non polar	33892256
1-Methylhistamine,1TBDMS,isomer #1	CN1C=NC(CCN[Si](C)(C)C(C)(C)C)=C1	2045.2	Standard polar	33892256
1-Methylhistamine,2TBDMS,isomer #1	CN1C=NC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2147.2	Semi standard non polar	33892256
1-Methylhistamine,2TBDMS,isomer #1	CN1C=NC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2184.9	Standard non polar	33892256
1-Methylhistamine,2TBDMS,isomer #1	CN1C=NC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2060.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 1-Methylhistamine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-0fki-3900000000-8197b65f233a917f6f5d	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1-Methylhistamine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00dr-3900000000-4a05dead99e371226a6c	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1-Methylhistamine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00di-9700000000-b8108f1cb31c26ab942f	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1-Methylhistamine GC-MS (2 TMS)	splash10-0fe0-5900000000-c04c884eec0846197eb8	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1-Methylhistamine EI-B (Non-derivatized)	splash10-00di-2910000000-3458f7def44a74d73f7b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1-Methylhistamine GC-EI-TOF (Non-derivatized)	splash10-0fki-3900000000-8197b65f233a917f6f5d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1-Methylhistamine GC-EI-TOF (Non-derivatized)	splash10-00dr-3900000000-4a05dead99e371226a6c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1-Methylhistamine GC-EI-TOF (Non-derivatized)	splash10-00di-9700000000-b8108f1cb31c26ab942f	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1-Methylhistamine GC-MS (Non-derivatized)	splash10-0fe0-5900000000-c04c884eec0846197eb8	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Methylhistamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001j-9200000000-f6dbf3d86200b3f6be5f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Methylhistamine 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methylhistamine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0a4i-0900000000-b77c6433a2a8bdb852dd	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methylhistamine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0aor-9600000000-a2a8c75c945ca81ded8a	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methylhistamine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-001i-9200000000-fa9fad79e09f38a3450d	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methylhistamine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF	splash10-004i-0900000000-b9f4341a558b04495c54	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methylhistamine LC-ESI-QTOF , positive-QTOF	splash10-004i-0900000000-b9f4341a558b04495c54	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methylhistamine 10V, Positive-QTOF	splash10-056r-0900000000-b9f2ff9fde6f1a170d38	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methylhistamine 20V, Positive-QTOF	splash10-0a4i-1900000000-0ad300b172fcdc68e104	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methylhistamine 40V, Positive-QTOF	splash10-0le9-9000000000-fe751072b0ecf7a0d5bf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methylhistamine 10V, Negative-QTOF	splash10-00di-0900000000-c7b86cf59142756c4f91	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methylhistamine 20V, Negative-QTOF	splash10-00di-3900000000-0bed565bcfefeb389d2b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methylhistamine 40V, Negative-QTOF	splash10-0arv-9100000000-fc2c7dc356034fe098ae	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methylhistamine 10V, Positive-QTOF	splash10-0a4i-0900000000-317df42b1c6c53a3cd83	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methylhistamine 20V, Positive-QTOF	splash10-0a4i-6900000000-e29c16ae4d103e7eaa01	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methylhistamine 40V, Positive-QTOF	splash10-066u-9000000000-2d8cc6d1c8601ed4eed0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methylhistamine 10V, Negative-QTOF	splash10-00di-1900000000-c5c45bb41ea05838fa94	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methylhistamine 20V, Negative-QTOF	splash10-00di-5900000000-68ef55e857c894f92309	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methylhistamine 40V, Negative-QTOF	splash10-014i-9000000000-434d60e1525fedada46a	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	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]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva
Urine

Tissue Locations

Bone Marrow
Brain

Pathways

Name	SMPDB/PathBank	KEGG
Histidine metabolism
Histidinemia		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.00034 (0.00021-0.00047) uM	Adult (>18 years old)	Both	Normal	9234842	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.002 +/- 0.0005 (0.0015 - 0.0025) uM	Adult (>18 years old)	Both	Normal	7164933	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.005 +/- 0.0006 (0.003-0.006) uM	Children (1-13 years old)	Both	Normal	7886118	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	1.12 +/- 0.22 uM	Adult (>18 years old)	Both	Normal	7711000	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.007 +/- 0.0005 (0.006 - 0.008) uM	Children (1-13 years old)	Not Specified	Normal	7886118	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.002209 +/- 0.000463 uM	Adult (>18 years old)	Not Specified	Normal	20932951	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00214 +/- 0.0001 uM	Not Specified	Not Specified	Normal	20858978	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Normal	27609529	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Saliva	Detected and Quantified	0.0117 +/- 0.0359 uM	Adult (>18 years old)	Both	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.0125 +/- 0.0348 uM	Adult (>18 years old)	Both	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.0301 +/- 0.0193 uM	Adult (>18 years old)	Both	Normal	Sugimoto et al. (...	details
Urine	Detected and Quantified	0.13 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	19309105	details
Urine	Detected and Quantified	0.098 (0.032-0.18) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ... West Cadwell, N.J... Basel, Switzerlan...	details
Urine	Detected and Quantified	0.065 (0.32-0.98) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	10027644	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00078 (0.00055-0.00100) uM	Adult (>18 years old)	Both	Dermal fibroproliferative disorder (hypertrophic scarring)	9234842	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.002431 +/- 0.000461 uM	Adult (>18 years old)	Not Specified	sporadic narcolepsy-cataplexy	20932951	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00276 +/- 0.00013 uM	Adult (>18 years old)	Not Specified	Alzheimer's disease	20858978	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00290 +/- 0.00027 uM	Adult (>18 years old)	Both	Schizophrenia	7711000	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	2.90 +/- 0.27 uM	Adult (>18 years old)	Both	Schizophrenia	7711000	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Crohns disease	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Ulcerative colitis	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Unclassified IBD	27609529	details
Saliva	Detected and Quantified	0.0203 +/- 0.0254 uM	Adult (>18 years old)	Both	Oral cavity disorders	Sugimoto et al. (...	details
Urine	Detected and Quantified	0.73 umol/mmol creatinine	Adult (>18 years old)	Both	Mastocytosis	10027644	details

Associated Disorders and Diseases

Disease References

Dermal fibroproliferative disorder
Tredget EE, Iwashina T, Scott PG, Ghahary A: Determination of plasma Ntau-methylhistamine in vivo by isotope dilution using benchtop gas chromatography-mass spectrometry. J Chromatogr B Biomed Sci Appl. 1997 Jun 20;694(1):1-9. [PubMed:9234842 ]
Alzheimer's disease
Motawaj M, Peoc'h K, Callebert J, Arrang JM: CSF levels of the histamine metabolite tele-methylhistamine are only slightly decreased in Alzheimer's disease. J Alzheimers Dis. 2010;22(3):861-71. doi: 10.3233/JAD-2010-100381. [PubMed:20858978 ]
Schizophrenia
Prell GD, Green JP, Kaufmann CA, Khandelwal JK, Morrishow AM, Kirch DG, Linnoila M, Wyatt RJ: Histamine metabolites in cerebrospinal fluid of patients with chronic schizophrenia: their relationships to levels of other aminergic transmitters and ratings of symptoms. Schizophr Res. 1995 Jan;14(2):93-104. [PubMed:7711000 ]
Crohn's disease
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Ulcerative colitis
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Mastocytosis
Martens-Lobenhoffer J, Neumann HJ: Determination of 1-methylhistamine and 1-methylimidazoleacetic acid in human urine as a tool for the diagnosis of mastocytosis. J Chromatogr B Biomed Sci Appl. 1999 Jan 8;721(1):135-40. [PubMed:10027644 ]

Associated OMIM IDs

104300 (Alzheimer's disease)
181500 (Schizophrenia)
266600 (Crohn's disease)
154800 (Mastocytosis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022306

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

29009

Food Biomarker Ontology

Not Available

VMH ID

MHISTA

MarkerDB ID

MDB00000278

Good Scents ID

Not Available

References

Synthesis Reference

Rothschild, Zuleika; Schayer, Richard W. Synthesis and metabolism of a histamine metabolite, 1-methyl-4-(b-aminoethyl)imidazole. Biochimica et Biophysica Acta (1958), 30 23-7.

Material Safety Data Sheet (MSDS)

Not Available

General References

Ito C: The role of the central histaminergic system on schizophrenia. Drug News Perspect. 2004 Jul-Aug;17(6):383-7. [PubMed:15334189 ]
Khandelwal JK, Hough LB, Morrishow AM, Green JP: Measurement of tele-methylhistamine and histamine in human cerebrospinal fluid, urine, and plasma. Agents Actions. 1982 Dec;12(5-6):583-90. [PubMed:7164933 ]
Winterkamp S, Weidenhiller M, Otte P, Stolper J, Schwab D, Hahn EG, Raithel M: Urinary excretion of N-methylhistamine as a marker of disease activity in inflammatory bowel disease. Am J Gastroenterol. 2002 Dec;97(12):3071-7. [PubMed:12492192 ]
Elmore BO, Bollinger JA, Dooley DM: Human kidney diamine oxidase: heterologous expression, purification, and characterization. J Biol Inorg Chem. 2002 Jun;7(6):565-79. Epub 2002 Feb 13. [PubMed:12072962 ]
Robbins IM, Barst RJ, Rubin LJ, Gaine SP, Price PV, Morrow JD, Christman BW: Increased levels of prostaglandin D(2) suggest macrophage activation in patients with primary pulmonary hypertension. Chest. 2001 Nov;120(5):1639-44. [PubMed:11713147 ]
O'Sullivan S, Roquet A, Dahlen B, Dahlen S, Kumlin M: Urinary excretion of inflammatory mediators during allergen-induced early and late phase asthmatic reactions. Clin Exp Allergy. 1998 Nov;28(11):1332-9. [PubMed:9824404 ]
Martens-Lobenhoffer J, Neumann HJ: Determination of 1-methylhistamine and 1-methylimidazoleacetic acid in human urine as a tool for the diagnosis of mastocytosis. J Chromatogr B Biomed Sci Appl. 1999 Jan 8;721(1):135-40. [PubMed:10027644 ]
Theoharides TC, Sant GR, el-Mansoury M, Letourneau R, Ucci AA Jr, Meares EM Jr: Activation of bladder mast cells in interstitial cystitis: a light and electron microscopic study. J Urol. 1995 Mar;153(3 Pt 1):629-36. [PubMed:7861501 ]
Brumsen C, Papapoulos SE, Lentjes EG, Kluin PM, Hamdy NA: A potential role for the mast cell in the pathogenesis of idiopathic osteoporosis in men. Bone. 2002 Nov;31(5):556-61. [PubMed:12477568 ]
Rozniecki JJ, Hauser SL, Stein M, Lincoln R, Theoharides TC: Elevated mast cell tryptase in cerebrospinal fluid of multiple sclerosis patients. Ann Neurol. 1995 Jan;37(1):63-6. [PubMed:7818259 ]
Alakarppa K, Tupala E, Mantere T, Sarkioja T, Rasanen P, Tarhanen J, Tiihonen J, Tuomisto L: Effect of alcohol abuse on human brain histamine and tele-methylhistamine. Inflamm Res. 2002 Apr;51 Suppl 1:S40-1. [PubMed:12013402 ]
Tredget EE, Iwashina T, Scott PG, Ghahary A: Determination of plasma Ntau-methylhistamine in vivo by isotope dilution using benchtop gas chromatography-mass spectrometry. J Chromatogr B Biomed Sci Appl. 1997 Jun 20;694(1):1-9. [PubMed:9234842 ]
van Toorenenbergen AW, Oranje AP: Comparison of serum tryptase and urine N-methylhistamine in patients with suspected mastocytosis. Clin Chim Acta. 2005 Sep;359(1-2):72-7. [PubMed:15913591 ]
Droogendijk HJ, Kluin-Nelemans HJ, van Doormaal JJ, Oranje AP, van de Loosdrecht AA, van Daele PL: Imatinib mesylate in the treatment of systemic mastocytosis: a phase II trial. Cancer. 2006 Jul 15;107(2):345-51. [PubMed:16779792 ]
Oranje AP, Mulder PG, Heide R, Tank B, Riezebos P, van Toorenenbergen AW: Urinary N-methylhistamine as an indicator of bone marrow involvement in mastocytosis. Clin Exp Dermatol. 2002 Sep;27(6):502-6. [PubMed:12372095 ]
Rinne JO, Anichtchik OV, Eriksson KS, Kaslin J, Tuomisto L, Kalimo H, Roytta M, Panula P: Increased brain histamine levels in Parkinson's disease but not in multiple system atrophy. J Neurochem. 2002 Jun;81(5):954-60. [PubMed:12065607 ]
Fitzpatrick MF, Mackay T, Walters C, Tai PC, Church MK, Holgate ST, Douglas NJ: Circulating histamine and eosinophil cationic protein levels in nocturnal asthma. Clin Sci (Lond). 1992 Aug;83(2):227-32. [PubMed:1327639 ]
Butterfield JH, Tefferi A, Kozuh GF: Successful treatment of systemic mastocytosis with high-dose interferon-alfa: long-term follow-up of a case. Leuk Res. 2005 Feb;29(2):131-4. [PubMed:15607359 ]
Winterkamp S, Weidenhiller M, Wilken V, Donhauser N, Schultis HW, Buchwald F, Hahn EG, Raithel M: Standardised evaluation of urinary excretion of N-tele-methylhistamine in different periods of age in a healthy population. Inflamm Res. 2003 Apr;52 Suppl 1:S57-8. [PubMed:12755411 ]
Coruzzi G, Morini G, Adami M, Grandi D: Role of histamine H3 receptors in the regulation of gastric functions. J Physiol Pharmacol. 2001 Dec;52(4 Pt 1):539-53. [PubMed:11787757 ]

Enzymes

Enzyme Details

1. Amine oxidase [flavin-containing] B

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:: MAOB
Uniprot ID:: P27338
Molecular weight:: 58762.475

Reactions

1-Methylhistamine + Water + Oxygen → Methylimidazole acetaldehyde + Ammonia + Hydrogen peroxide	details

Enzyme Details

2. Amine oxidase [flavin-containing] A

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:: MAOA
Uniprot ID:: P21397
Molecular weight:: 59681.27

Reactions

1-Methylhistamine + Water + Oxygen → Methylimidazole acetaldehyde + Ammonia + Hydrogen peroxide	details

Enzyme Details

3. Histamine N-methyltransferase

General function:: Involved in histamine N-methyltransferase activity
Specific function:: Inactivates histamine by N-methylation. Plays an important role in degrading histamine and in regulating the airway response to histamine.
Gene Name:: HNMT
Uniprot ID:: P50135
Molecular weight:: 6045.9

Reactions

S-Adenosylmethionine + Histamine → S-Adenosylhomocysteine + 1-Methylhistamine	details

Showing metabocard for 1-Methylhistamine (HMDB0000898)

MOL for HMDB0000898 (1-Methylhistamine)

3D MOL for HMDB0000898 (1-Methylhistamine)

3D SDF for HMDB0000898 (1-Methylhistamine)

3D-SDF for HMDB0000898 (1-Methylhistamine)

PDB for HMDB0000898 (1-Methylhistamine)

3D PDB for HMDB0000898 (1-Methylhistamine)

SMILES for HMDB0000898 (1-Methylhistamine)

INCHI for HMDB0000898 (1-Methylhistamine)

Structure for HMDB0000898 (1-Methylhistamine)

3D Structure for HMDB0000898 (1-Methylhistamine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions

Reactions