MiMeDB: Showing metabocard for 1-Methylhistamine (MMDBc0000557)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:40:28 UTC

Update Date

2024-04-30 19:32:59 UTC

Metabolite ID

MMDBc0000557

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

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

Molecular Formula

C₆H₁₁N₃

Average Mass

125.1716

Monoisotopic Mass

125.095297367

IUPAC Name

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

Traditional Name

methylhistamine

CAS Registry Number

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

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	Yes	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	Deposition Date	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	2014-06-16	View 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	2014-06-16	View 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	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0fe0-5900000000-c04c884eec0846197eb8	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-2910000000-3458f7def44a74d73f7b	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0fki-3900000000-8197b65f233a917f6f5d	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00dr-3900000000-4a05dead99e371226a6c	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9700000000-b8108f1cb31c26ab942f	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0fe0-5900000000-c04c884eec0846197eb8	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001j-9200000000-f6dbf3d86200b3f6be5f	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0a4i-0900000000-b77c6433a2a8bdb852dd	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0aor-9600000000-a2a8c75c945ca81ded8a	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-001i-9200000000-fa9fad79e09f38a3450d	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-004i-0900000000-b9f4341a558b04495c54	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-004i-0900000000-b9f4341a558b04495c54	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-0900000000-b9f2ff9fde6f1a170d38	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-1900000000-0ad300b172fcdc68e104	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0le9-9000000000-fe751072b0ecf7a0d5bf	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-c7b86cf59142756c4f91	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-3900000000-0bed565bcfefeb389d2b	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0arv-9100000000-fc2c7dc356034fe098ae	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-317df42b1c6c53a3cd83	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-6900000000-e29c16ae4d103e7eaa01	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-066u-9000000000-2d8cc6d1c8601ed4eed0	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-1900000000-c5c45bb41ea05838fa94	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-5900000000-68ef55e857c894f92309	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-9000000000-434d60e1525fedada46a	2021-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Bone Marrow
Brain
Cerebrospinal Fluid (CSF)
Feces
Saliva
Urine

Tissue Locations

Bone Marrow
Brain

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191832	Amine oxidase [flavin-containing] B	Unknown	P27338	Homo sapiens
MMDBp0191840	Amine oxidase [flavin-containing] A	Unknown	P21397	Homo sapiens
MMDBp0192093	Histamine N-methyltransferase	Unknown	P50135	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0001654	1-Methylhistamine	Methylimidazole acetaldehyde	amine oxidase, copper containing 1		VMH	12072962 15035803 8920635 9653080
MMDBr0002089	S-Adenosylmethionine	S-Adenosylhomocysteine	histamine N-methyltransferase		VMH; KEGG	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Alzheimer's disease	Slight Increase	Association	Human Cerebrospinal Fluid (CSF)	HMDB	20858978
Dermal fibroproliferative disorder	Increased	Association	Human Blood	HMDB	9234842
Mastocytosis	Increased	Association	Human Urine	HMDB	10027644
Schizophrenia		Association	Human Cerebrospinal Fluid (CSF)	HMDB	7711000

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human ; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Firmicutes	1	Human ; Human mucosa	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.00276	0.00013			uM	Adult (>18 years old)	Not Specified	Alzheimer's disease	HMDB	20858978
Human Blood	Detected and Quantified	0.00078		0.00055	0.00100	uM	Adult (>18 years old)	Both	Dermal fibroproliferative disorder (hypertrophic scarring)	HMDB	9234842
Human Urine	Detected and Quantified	0.73				umol/mmol creatinine	Adult (>18 years old)	Both	Mastocytosis	HMDB	10027644
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.00290	0.00027			uM	Adult (>18 years old)	Both	Schizophrenia	HMDB	7711000
Human Cerebrospinal fluid (csf)	Detected and Quantified	2.90	0.27			uM	Adult (>18 years old)	Both	Schizophrenia	HMDB	7711000
Human Urine	Detected and Quantified	0.13				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	19309105
Human Blood	Detected and Quantified	0.00034		0.00021	0.00047	uM	Adult (>18 years old)	Both	Normal	HMDB	9234842
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.002 +/- 0.0005		0.0015	0.0025	uM	Adult (>18 years old)	Both	Normal	HMDB	7164933
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.00214	0.0001			uM	Not Specified	Not Specified	Normal	HMDB	20858978
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.002209	0.000463			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	20932951
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.005 +/- 0.0006		0.003	0.006	uM	Children (1-13 years old)	Both	Normal	HMDB	7886118
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.007 +/- 0.0005		0.006	0.008	uM	Children (1-13 years old)	Not Specified	Normal	HMDB	7886118
Human Urine	Detected and Quantified	0.065		0.32	0.98	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	10027644
Human Cerebrospinal fluid (csf)	Detected and Quantified	1.12	0.22			uM	Adult (>18 years old)	Both	Normal	HMDB	7711000
Human Urine	Detected and Quantified	0.098		0.032	0.18	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Saliva	Detected and Quantified	0.0117	0.0359			uM	Adult (>18 years old)	Both	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.0125	0.0348			uM	Adult (>18 years old)	Both	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.0301	0.0193			uM	Adult (>18 years old)	Both	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Bone marrow	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Brain	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified						Children (6 - 18 years old)	Not Specified	Normal	HMDB	27609529
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000898

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

References

Synthesis Reference

Not Available

General References

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. doi: 10.1042/cs0830227. [PubMed:1327639 ]
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. doi: 10.1007/BF01965064. [PubMed:7164933 ]
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. doi: 10.1002/ana.410370112. [PubMed:7818259 ]
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. doi: 10.1097/00005392-199503000-00021. [PubMed:7861501 ]
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. doi: 10.1016/s0378-4347(97)00122-9. [PubMed:9234842 ]
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. doi: 10.1046/j.1365-2222.1998.00368.x. [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. doi: 10.1016/s0378-4347(98)00481-2. [PubMed:10027644 ]
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. doi: 10.1378/chest.120.5.1639. [PubMed:11713147 ]
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 ]
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. doi: 10.1007/pl00022438. [PubMed:12013402 ]
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. doi: 10.1046/j.1471-4159.2002.00871.x. [PubMed:12065607 ]
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. doi: 10.1007/s00775-001-0331-1. Epub 2002 Feb 13. [PubMed:12072962 ]
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. doi: 10.1046/j.1365-2230.2002.01072.x. [PubMed:12372095 ]
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. doi: 10.1016/s8756-3282(02)00875-x. [PubMed:12477568 ]
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. doi: 10.1111/j.1572-0241.2002.07028.x. [PubMed:12492192 ]
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. doi: 10.1007/s000110300054. [PubMed:12755411 ]
Ito C: The role of the central histaminergic system on schizophrenia. Drug News Perspect. 2004 Jul-Aug;17(6):383-7. doi: 10.1358/dnp.2004.17.6.829029. [PubMed:15334189 ]
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. doi: 10.1016/j.leukres.2004.05.003. [PubMed:15607359 ]
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. doi: 10.1016/j.cccn.2005.03.041. [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. doi: 10.1002/cncr.21996. [PubMed:16779792 ]

Showing metabocard for 1-Methylhistamine (MMDBc0000557)

MOL for #<Metabolite:0x00007fdb503cc638>

3D MOL for #<Metabolite:0x00007fdb503cc638>

3D SDF for #<Metabolite:0x00007fdb503cc638>

3D-SDF for #<Metabolite:0x00007fdb503cc638>

PDB for #<Metabolite:0x00007fdb503cc638>

3D PDB for #<Metabolite:0x00007fdb503cc638>

SMILES for #<Metabolite:0x00007fdb503cc638>

INCHI for #<Metabolite:0x00007fdb503cc638>

Structure for #<Metabolite:0x00007fdb503cc638>

3D Structure for #<Metabolite:0x00007fdb503cc638>