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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2014-04-16 18:06:21 UTC

Update Date

2023-02-21 17:30:25 UTC

HMDB ID

HMDB0061685

Secondary Accession Numbers

HMDB61685

Metabolite Identification

Common Name

N-Methylhistamine

Description

N-Methylhistamine belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group. N-Methylhistamine is a very strong basic compound (based on its pKa).

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Nalpha-methylhistamine	HMDB
N-a-Methylhistamine	HMDB
N-Α-methylhistamine	HMDB
N(alpha)-Methylhistamine	HMDB
N-Methylhistamine	MeSH

Chemical Formula

C₆H₁₁N₃

Average Molecular Weight

125.1716

Monoisotopic Molecular Weight

125.095297367

IUPAC Name

[2-(1H-imidazol-5-yl)ethyl](methyl)amine

Traditional Name

[2-(3H-imidazol-4-yl)ethyl](methyl)amine

CAS Registry Number

Not Available

SMILES

CNCCC1=CN=CN1

InChI Identifier

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

InChI Key

PHSPJQZRQAJPPF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Aralkylamines

Alternative Parents

Substituents

Aralkylamine
Heteroaromatic compound
Imidazole
Azole
Azacycle
Organoheterocyclic compound
Secondary amine
Secondary aliphatic amine
Organopnictogen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0061685)

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	130 g/L	ALOGPS
logP	-0.37	ALOGPS
logP	-0.61	ChemAxon
logS	0.02	ALOGPS
pKa (Strongest Acidic)	13.5	ChemAxon
pKa (Strongest Basic)	9.85	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.71 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	37 m³·mol⁻¹	ChemAxon
Polarizability	14.05 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]+	125.088	31661259
DarkChem	[M-H]-	119.743	31661259
DeepCCS	[M+H]+	125.465	30932474
DeepCCS	[M-H]-	123.086	30932474
DeepCCS	[M-2H]-	159.239	30932474
DeepCCS	[M+Na]+	133.719	30932474
AllCCS	[M+H]+	127.2	32859911
AllCCS	[M+H-H2O]+	122.6	32859911
AllCCS	[M+NH4]+	131.6	32859911
AllCCS	[M+Na]+	132.8	32859911
AllCCS	[M-H]-	127.3	32859911
AllCCS	[M+Na-2H]-	129.5	32859911
AllCCS	[M+HCOO]-	132.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.61 minutes	32390414
Predicted by Siyang on May 30, 2022	7.9459 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	7.57 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	360.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	274.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	53.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	181.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	61.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	276.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	229.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	909.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	527.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	36.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	599.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	190.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	264.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	739.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	601.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	257.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Methylhistamine	CNCCC1=CN=CN1	2114.7	Standard polar	33892256
N-Methylhistamine	CNCCC1=CN=CN1	1335.6	Standard non polar	33892256
N-Methylhistamine	CNCCC1=CN=CN1	1367.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Methylhistamine,1TMS,isomer #1	CN(CCC1=CN=C[NH]1)[Si](C)(C)C	1463.4	Semi standard non polar	33892256
N-Methylhistamine,1TMS,isomer #1	CN(CCC1=CN=C[NH]1)[Si](C)(C)C	1583.4	Standard non polar	33892256
N-Methylhistamine,1TMS,isomer #1	CN(CCC1=CN=C[NH]1)[Si](C)(C)C	1908.9	Standard polar	33892256
N-Methylhistamine,1TMS,isomer #2	CNCCC1=CN=CN1[Si](C)(C)C	1439.7	Semi standard non polar	33892256
N-Methylhistamine,1TMS,isomer #2	CNCCC1=CN=CN1[Si](C)(C)C	1440.3	Standard non polar	33892256
N-Methylhistamine,1TMS,isomer #2	CNCCC1=CN=CN1[Si](C)(C)C	1844.5	Standard polar	33892256
N-Methylhistamine,2TMS,isomer #1	CN(CCC1=CN=CN1[Si](C)(C)C)[Si](C)(C)C	1663.5	Semi standard non polar	33892256
N-Methylhistamine,2TMS,isomer #1	CN(CCC1=CN=CN1[Si](C)(C)C)[Si](C)(C)C	1660.4	Standard non polar	33892256
N-Methylhistamine,2TMS,isomer #1	CN(CCC1=CN=CN1[Si](C)(C)C)[Si](C)(C)C	1769.5	Standard polar	33892256
N-Methylhistamine,1TBDMS,isomer #1	CN(CCC1=CN=C[NH]1)[Si](C)(C)C(C)(C)C	1661.3	Semi standard non polar	33892256
N-Methylhistamine,1TBDMS,isomer #1	CN(CCC1=CN=C[NH]1)[Si](C)(C)C(C)(C)C	1850.2	Standard non polar	33892256
N-Methylhistamine,1TBDMS,isomer #1	CN(CCC1=CN=C[NH]1)[Si](C)(C)C(C)(C)C	2050.3	Standard polar	33892256
N-Methylhistamine,1TBDMS,isomer #2	CNCCC1=CN=CN1[Si](C)(C)C(C)(C)C	1681.0	Semi standard non polar	33892256
N-Methylhistamine,1TBDMS,isomer #2	CNCCC1=CN=CN1[Si](C)(C)C(C)(C)C	1665.9	Standard non polar	33892256
N-Methylhistamine,1TBDMS,isomer #2	CNCCC1=CN=CN1[Si](C)(C)C(C)(C)C	1966.8	Standard polar	33892256
N-Methylhistamine,2TBDMS,isomer #1	CN(CCC1=CN=CN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2104.3	Semi standard non polar	33892256
N-Methylhistamine,2TBDMS,isomer #1	CN(CCC1=CN=CN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2108.6	Standard non polar	33892256
N-Methylhistamine,2TBDMS,isomer #1	CN(CCC1=CN=CN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1986.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Methylhistamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-1e85a9d5fe04d6a70ec5	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-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 - N-Methylhistamine 35V, Positive-QTOF	splash10-000t-9000000000-4400f17c1a3795139b3f	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylhistamine 10V, Positive-QTOF	splash10-004j-5900000000-79bb5ea9b1bfe0168c87	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylhistamine 20V, Positive-QTOF	splash10-002b-9300000000-f4a3a6252857a3b4cf1b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylhistamine 40V, Positive-QTOF	splash10-0gba-9000000000-9042f89af7ddba0f8f41	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylhistamine 10V, Negative-QTOF	splash10-00di-1900000000-2f2da436eedbebff67c8	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylhistamine 20V, Negative-QTOF	splash10-00di-6900000000-ffea31778ce93c31ff91	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylhistamine 40V, Negative-QTOF	splash10-0f8c-9000000000-ff331d70a1512232c106	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylhistamine 10V, Negative-QTOF	splash10-00di-0900000000-cbe069dfb788d58d0971	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylhistamine 20V, Negative-QTOF	splash10-00di-9500000000-57cea8ca9b44e46a9920	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylhistamine 40V, Negative-QTOF	splash10-014l-9000000000-29e08ea8119d60df1eb0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylhistamine 10V, Positive-QTOF	splash10-004j-9800000000-b654a1a628a844259145	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylhistamine 20V, Positive-QTOF	splash10-0002-9000000000-f61007d883cb6f7de18f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylhistamine 40V, Positive-QTOF	splash10-0537-9000000000-51f19a5de5ce39500b39	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Methylhistamine

METLIN ID

Not Available

PubChem Compound

912

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 N-Methylhistamine (HMDB0061685)

MOL for HMDB0061685 (N-Methylhistamine)

3D MOL for HMDB0061685 (N-Methylhistamine)

3D SDF for HMDB0061685 (N-Methylhistamine)

3D-SDF for HMDB0061685 (N-Methylhistamine)

PDB for HMDB0061685 (N-Methylhistamine)

3D PDB for HMDB0061685 (N-Methylhistamine)

SMILES for HMDB0061685 (N-Methylhistamine)

INCHI for HMDB0061685 (N-Methylhistamine)

Structure for HMDB0061685 (N-Methylhistamine)

3D Structure for HMDB0061685 (N-Methylhistamine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra