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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-02-22 11:40:36 UTC

Update Date

2023-02-21 17:15:51 UTC

HMDB ID

HMDB0001861

Secondary Accession Numbers

HMDB01861

Metabolite Identification

Common Name

3-Methylhistamine

Description

3-Methylhistamine 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. 3-Methylhistamine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 3-methylhistamine a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on 3-Methylhistamine.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
L-Histamine deriv. 1	HMDB
N(T)-Methylhistamine	HMDB
N(Tau)-methylhistamine	HMDB
N-Tau-methylhistamine	HMDB, MeSH
Tau-methylhistamine	HMDB, MeSH
3-Methylhistamine dihydrochloride	MeSH, HMDB
3-Methylhistamine	MeSH

Chemical Formula

C₆H₁₁N₃

Average Molecular Weight

125.1716

Monoisotopic Molecular Weight

125.095297367

IUPAC Name

2-(1-methyl-1H-imidazol-5-yl)ethan-1-amine

Traditional Name

3-methylhistamine

CAS Registry Number

644-42-8

SMILES

CN1C=NC=C1CCN

InChI Identifier

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

InChI Key

CPAGZVLINCPJEH-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

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0001861)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0001861)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0001861)

Source

Endogenous

Endogenous (HMDB: HMDB0001861)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
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)

Equine

Horse (FooDB: FOOD00378)

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)

Process

Not Available

Role

Not Available

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	126.533	30932474
[M+H]+	MetCCS_train_pos	123.752	30932474
[M+H]+	Not Available	124.4	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000539

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.85 g/L	ALOGPS
logP	-0.83	ALOGPS
logP	-0.82	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Basic)	9.78	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	43.84 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	37.13 m³·mol⁻¹	ChemAxon
Polarizability	13.92 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]+	124.256	31661259
DarkChem	[M-H]-	120.558	31661259
AllCCS	[M+H]+	126.859	32859911
AllCCS	[M-H]-	125.901	32859911
DeepCCS	[M+H]+	124.465	30932474
DeepCCS	[M-H]-	121.882	30932474
DeepCCS	[M-2H]-	158.307	30932474
DeepCCS	[M+Na]+	133.295	30932474
AllCCS	[M+H]+	126.9	32859911
AllCCS	[M+H-H2O]+	122.2	32859911
AllCCS	[M+NH4]+	131.2	32859911
AllCCS	[M+Na]+	132.5	32859911
AllCCS	[M-H]-	125.9	32859911
AllCCS	[M+Na-2H]-	128.1	32859911
AllCCS	[M+HCOO]-	130.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Methylhistamine	CN1C=NC=C1CCN	2167.4	Standard polar	33892256
3-Methylhistamine	CN1C=NC=C1CCN	1436.1	Standard non polar	33892256
3-Methylhistamine	CN1C=NC=C1CCN	1372.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Methylhistamine,1TMS,isomer #1	CN1C=NC=C1CCN[Si](C)(C)C	1496.1	Semi standard non polar	33892256
3-Methylhistamine,1TMS,isomer #1	CN1C=NC=C1CCN[Si](C)(C)C	1561.9	Standard non polar	33892256
3-Methylhistamine,1TMS,isomer #1	CN1C=NC=C1CCN[Si](C)(C)C	1878.7	Standard polar	33892256
3-Methylhistamine,2TMS,isomer #1	CN1C=NC=C1CCN([Si](C)(C)C)[Si](C)(C)C	1742.7	Semi standard non polar	33892256
3-Methylhistamine,2TMS,isomer #1	CN1C=NC=C1CCN([Si](C)(C)C)[Si](C)(C)C	1777.3	Standard non polar	33892256
3-Methylhistamine,2TMS,isomer #1	CN1C=NC=C1CCN([Si](C)(C)C)[Si](C)(C)C	1849.8	Standard polar	33892256
3-Methylhistamine,1TBDMS,isomer #1	CN1C=NC=C1CCN[Si](C)(C)C(C)(C)C	1739.9	Semi standard non polar	33892256
3-Methylhistamine,1TBDMS,isomer #1	CN1C=NC=C1CCN[Si](C)(C)C(C)(C)C	1801.0	Standard non polar	33892256
3-Methylhistamine,1TBDMS,isomer #1	CN1C=NC=C1CCN[Si](C)(C)C(C)(C)C	1996.9	Standard polar	33892256
3-Methylhistamine,2TBDMS,isomer #1	CN1C=NC=C1CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2131.8	Semi standard non polar	33892256
3-Methylhistamine,2TBDMS,isomer #1	CN1C=NC=C1CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2202.8	Standard non polar	33892256
3-Methylhistamine,2TBDMS,isomer #1	CN1C=NC=C1CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2028.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methylhistamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001j-9200000000-052f704135f11d74ed40	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methylhistamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-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 - 3-Methylhistamine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-056s-2900000000-c9f454504e6359b0b0be	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylhistamine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0002-9200000000-8ce6c84f30341c8124e9	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylhistamine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-00lr-9000000000-dbef26b4250bbde784a8	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylhistamine , positive-QTOF	splash10-004i-0900000000-05db0a907f55fd5697b3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylhistamine 35V, Positive-QTOF	splash10-004i-0900000000-6bb37dbd89e15ed1ff0b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylhistamine 10V, Positive-QTOF	splash10-004i-1900000000-054aff5c788523f9fb69	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylhistamine 35V, Positive-QTOF	splash10-004i-0900000000-b1a73061bf275ded0bb6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylhistamine 35V, Positive-QTOF	splash10-004i-0900000000-7f98177798dededd8b8a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylhistamine 40V, Positive-QTOF	splash10-0fr2-9000000000-d746354f237ae0d5c8ca	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylhistamine 20V, Positive-QTOF	splash10-0002-9200000000-515b613508cc66073320	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylhistamine 40V, Positive-QTOF	splash10-0002-9000000000-d86d2dcd3ee01a3bb1d1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylhistamine 10V, Positive-QTOF	splash10-004i-1900000000-0e1bd2d92202d959dd58	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylhistamine 20V, Positive-QTOF	splash10-0002-9200000000-f506556ec8dce3bed55d	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylhistamine 10V, Positive-QTOF	splash10-056r-0900000000-70a4f63c7c70678531b6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylhistamine 20V, Positive-QTOF	splash10-0a4i-3900000000-bb58b80ce0d729f81a6c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylhistamine 40V, Positive-QTOF	splash10-014i-9000000000-863d517768f138904f02	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylhistamine 10V, Negative-QTOF	splash10-00di-1900000000-a6d65a6f86b3c40f4626	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylhistamine 20V, Negative-QTOF	splash10-00di-3900000000-58dfa354fec01badb28b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylhistamine 40V, Negative-QTOF	splash10-0a6r-9100000000-601c15d8230e0983d2e9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylhistamine 10V, Positive-QTOF	splash10-056r-2900000000-ab3814c48d66a74e0117	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylhistamine 20V, Positive-QTOF	splash10-0a59-8900000000-f5a1919f413b6efc109d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylhistamine 40V, Positive-QTOF	splash10-05o3-9000000000-0b568a6f55699dc3d877	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylhistamine 10V, Negative-QTOF	splash10-00di-3900000000-14f3c97f00ccfa6fa446	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylhistamine 20V, Negative-QTOF	splash10-0603-9500000000-084b1cab57e4da1aac12	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylhistamine 40V, Negative-QTOF	splash10-06r6-9000000000-56ef0c724afe8a89402b	2021-09-22	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	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 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
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 (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.011 +/- 0.03 uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	0.13 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	19309105	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

FDB022715

KNApSAcK ID

Not Available

Chemspider ID

62725

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Methylhistamine

METLIN ID

6355

PubChem Compound

69520

PDB ID

Not Available

ChEBI ID

114444

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)

Download (PDF)

General References

Keyzer JJ, Breukelman H, Wolthers BG, Richardson FJ, de Monchy JG: Measurement of N tau-methylhistamine concentrations in plasma and urine as a parameter for histamine release during anaphylactoid reactions. Agents Actions. 1985 Apr;16(3-4):76-9. [PubMed:2409780 ]
Murray S, Wellings R, Taylor IK, Fuller RW, Taylor GW: Gas chromatographic-mass spectrometric assay to measure urinary N tau-methylhistamine excretion in man. J Chromatogr. 1991 Jul 5;567(2):289-98. [PubMed:1939463 ]
Mita H, Yasueda H, Shida T: Simultaneous determination of histamine and N tau-methylhistamine in human plasma and urine by gas chromatography--mass spectrometry. J Chromatogr. 1980 Nov 14;221(1):1-7. [PubMed:7451611 ]

Showing metabocard for 3-Methylhistamine (HMDB0001861)

MOL for HMDB0001861 (3-Methylhistamine)

3D MOL for HMDB0001861 (3-Methylhistamine)

3D SDF for HMDB0001861 (3-Methylhistamine)

3D-SDF for HMDB0001861 (3-Methylhistamine)

PDB for HMDB0001861 (3-Methylhistamine)

3D PDB for HMDB0001861 (3-Methylhistamine)

SMILES for HMDB0001861 (3-Methylhistamine)

INCHI for HMDB0001861 (3-Methylhistamine)

Structure for HMDB0001861 (3-Methylhistamine)

3D Structure for HMDB0001861 (3-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