ContaminantDB: 1-Methylhistamine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (3)XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:37:37 UTC

Update Date

2026-04-06 11:04:26 UTC

Accession Number

CHEM003340

Identification

Common Name

1-Methylhistamine

Class

Small Molecule

Description

1-Methylhistamine is a histamine metabolite. It is a product of histamine 1-methyltransferase [EC 2.1.1.8] in the pathway histidine metabolism (KEGG).

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine
T3DB toxins

Contaminant Type

Amine
Animal Toxin
Food Toxin
Metabolite
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

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 Mass

125.172 g/mol

Monoisotopic Mass

125.095 g/mol

CAS Registry Number

501-75-7

IUPAC Name

Not Available

Traditional Name

methylhistamine

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 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Bone Marrow
Brain
Mast Cell

Pathways

Name	SMPDB Link	KEGG Link
Histidine Metabolism	SMP00044	map00340
Histidinemia	SMP00191	Not Available

Applications

Not Available

Biological Roles

human metabolite

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted 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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-0fki-3900000000-8197b65f233a917f6f5d	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00dr-3900000000-4a05dead99e371226a6c	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00di-9700000000-b8108f1cb31c26ab942f	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0fe0-5900000000-c04c884eec0846197eb8	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-2910000000-3458f7def44a74d73f7b	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0fki-3900000000-8197b65f233a917f6f5d	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00dr-3900000000-4a05dead99e371226a6c	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9700000000-b8108f1cb31c26ab942f	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0fe0-5900000000-c04c884eec0846197eb8	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001j-9200000000-f6dbf3d86200b3f6be5f	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0a4i-0900000000-b77c6433a2a8bdb852dd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0aor-9600000000-a2a8c75c945ca81ded8a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-001i-9200000000-fa9fad79e09f38a3450d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-004i-0900000000-b9f4341a558b04495c54	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-004i-0900000000-b9f4341a558b04495c54	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-0900000000-b9f2ff9fde6f1a170d38	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-1900000000-0ad300b172fcdc68e104	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0le9-9000000000-fe751072b0ecf7a0d5bf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-c7b86cf59142756c4f91	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-3900000000-0bed565bcfefeb389d2b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0arv-9100000000-fc2c7dc356034fe098ae	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-317df42b1c6c53a3cd83	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-6900000000-e29c16ae4d103e7eaa01	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-066u-9000000000-2d8cc6d1c8601ed4eed0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-1900000000-c5c45bb41ea05838fa94	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-5900000000-68ef55e857c894f92309	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-9000000000-434d60e1525fedada46a	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0000898

FooDB ID

FDB022306

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

45171

BioCyc ID

N-METHYL-HISTAMINE

METLIN ID

5854

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

M2MDB005083

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.

MSDS

Link

General References

1. 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.

2. 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.

3. 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.

4. Ito C: The role of the central histaminergic system on schizophrenia. Drug News Perspect. 2004 Jul-Aug;17(6):383-7.

5. 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.

6. 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.

7. 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.

8. 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.

9. 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.