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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 20:54:48 UTC

Update Date

2021-09-26 22:50:51 UTC

HMDB ID

HMDB0243669

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(R)-alpha-Methylhistamine

Description

alpha-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. alpha-methylhistamine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on alpha-methylhistamine. This compound has been identified in human blood as reported by (PMID: 31557052 ). (r)-alpha-methylhistamine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (R)-alpha-Methylhistamine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
a-Methylhistamine	Generator
Α-methylhistamine	Generator
alpha-Methylhistamine, (R)-isomer	MeSH
alpha-Methylhistamine dihydrochloride	MeSH
alpha-Methylhistamine, (S)-isomer	MeSH

Chemical Formula

C₆H₁₁N₃

Average Molecular Weight

125.175

Monoisotopic Molecular Weight

125.095297366

IUPAC Name

1-(1H-imidazol-5-yl)propan-2-amine

Traditional Name

α-methylhistamine

CAS Registry Number

Not Available

SMILES

CC(N)CC1=CN=CN1

InChI Identifier

InChI=1S/C6H11N3/c1-5(7)2-6-3-8-4-9-6/h3-5H,2,7H2,1H3,(H,8,9)

InChI Key

XNQIOISZPFVUFG-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
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Primary aliphatic amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

imidazoles (CHEBI:74759 )
aralkylamino compound (CHEBI:74759 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

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
logP	-0.39	ALOGPS
logP	-0.62	ChemAxon
logS	0.17	ALOGPS
pKa (Strongest Acidic)	13.48	ChemAxon
pKa (Strongest Basic)	10.01	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	54.7 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	36.65 m³·mol⁻¹	ChemAxon
Polarizability	13.71 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
DeepCCS	[M+H]+	126.689	30932474
DeepCCS	[M-H]-	124.043	30932474
DeepCCS	[M-2H]-	160.736	30932474
DeepCCS	[M+Na]+	135.484	30932474
AllCCS	[M+H]+	127.8	32859911
AllCCS	[M+H-H2O]+	123.1	32859911
AllCCS	[M+NH4]+	132.2	32859911
AllCCS	[M+Na]+	133.4	32859911
AllCCS	[M-H]-	126.1	32859911
AllCCS	[M+Na-2H]-	128.3	32859911
AllCCS	[M+HCOO]-	130.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	8.2966 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.23 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	378.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	281.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	51.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	174.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	55.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	282.6 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	225.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	816.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	545.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	33.7 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	562.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	183.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	278.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	651.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	626.6 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	311.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(R)-alpha-Methylhistamine	CC(N)CC1=CN=CN1	2228.6	Standard polar	33892256
(R)-alpha-Methylhistamine	CC(N)CC1=CN=CN1	1350.8	Standard non polar	33892256
(R)-alpha-Methylhistamine	CC(N)CC1=CN=CN1	1422.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(R)-alpha-Methylhistamine,1TMS,isomer #1	CC(CC1=CN=C[NH]1)N[Si](C)(C)C	1507.9	Semi standard non polar	33892256
(R)-alpha-Methylhistamine,1TMS,isomer #1	CC(CC1=CN=C[NH]1)N[Si](C)(C)C	1530.9	Standard non polar	33892256
(R)-alpha-Methylhistamine,1TMS,isomer #1	CC(CC1=CN=C[NH]1)N[Si](C)(C)C	1876.8	Standard polar	33892256
(R)-alpha-Methylhistamine,1TMS,isomer #2	CC(N)CC1=CN=CN1[Si](C)(C)C	1480.5	Semi standard non polar	33892256
(R)-alpha-Methylhistamine,1TMS,isomer #2	CC(N)CC1=CN=CN1[Si](C)(C)C	1519.6	Standard non polar	33892256
(R)-alpha-Methylhistamine,1TMS,isomer #2	CC(N)CC1=CN=CN1[Si](C)(C)C	2082.8	Standard polar	33892256
(R)-alpha-Methylhistamine,2TMS,isomer #1	CC(CC1=CN=CN1[Si](C)(C)C)N[Si](C)(C)C	1605.3	Semi standard non polar	33892256
(R)-alpha-Methylhistamine,2TMS,isomer #1	CC(CC1=CN=CN1[Si](C)(C)C)N[Si](C)(C)C	1598.8	Standard non polar	33892256
(R)-alpha-Methylhistamine,2TMS,isomer #1	CC(CC1=CN=CN1[Si](C)(C)C)N[Si](C)(C)C	1787.0	Standard polar	33892256
(R)-alpha-Methylhistamine,2TMS,isomer #2	CC(CC1=CN=C[NH]1)N([Si](C)(C)C)[Si](C)(C)C	1677.2	Semi standard non polar	33892256
(R)-alpha-Methylhistamine,2TMS,isomer #2	CC(CC1=CN=C[NH]1)N([Si](C)(C)C)[Si](C)(C)C	1734.5	Standard non polar	33892256
(R)-alpha-Methylhistamine,2TMS,isomer #2	CC(CC1=CN=C[NH]1)N([Si](C)(C)C)[Si](C)(C)C	1877.3	Standard polar	33892256
(R)-alpha-Methylhistamine,3TMS,isomer #1	CC(CC1=CN=CN1[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1827.0	Semi standard non polar	33892256
(R)-alpha-Methylhistamine,3TMS,isomer #1	CC(CC1=CN=CN1[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1780.6	Standard non polar	33892256
(R)-alpha-Methylhistamine,3TMS,isomer #1	CC(CC1=CN=CN1[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1804.0	Standard polar	33892256
(R)-alpha-Methylhistamine,1TBDMS,isomer #1	CC(CC1=CN=C[NH]1)N[Si](C)(C)C(C)(C)C	1731.5	Semi standard non polar	33892256
(R)-alpha-Methylhistamine,1TBDMS,isomer #1	CC(CC1=CN=C[NH]1)N[Si](C)(C)C(C)(C)C	1771.4	Standard non polar	33892256
(R)-alpha-Methylhistamine,1TBDMS,isomer #1	CC(CC1=CN=C[NH]1)N[Si](C)(C)C(C)(C)C	2011.7	Standard polar	33892256
(R)-alpha-Methylhistamine,1TBDMS,isomer #2	CC(N)CC1=CN=CN1[Si](C)(C)C(C)(C)C	1712.8	Semi standard non polar	33892256
(R)-alpha-Methylhistamine,1TBDMS,isomer #2	CC(N)CC1=CN=CN1[Si](C)(C)C(C)(C)C	1718.1	Standard non polar	33892256
(R)-alpha-Methylhistamine,1TBDMS,isomer #2	CC(N)CC1=CN=CN1[Si](C)(C)C(C)(C)C	2188.7	Standard polar	33892256
(R)-alpha-Methylhistamine,2TBDMS,isomer #1	CC(CC1=CN=CN1[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	2084.7	Semi standard non polar	33892256
(R)-alpha-Methylhistamine,2TBDMS,isomer #1	CC(CC1=CN=CN1[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	2017.4	Standard non polar	33892256
(R)-alpha-Methylhistamine,2TBDMS,isomer #1	CC(CC1=CN=CN1[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	1994.4	Standard polar	33892256
(R)-alpha-Methylhistamine,2TBDMS,isomer #2	CC(CC1=CN=C[NH]1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2079.5	Semi standard non polar	33892256
(R)-alpha-Methylhistamine,2TBDMS,isomer #2	CC(CC1=CN=C[NH]1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2179.4	Standard non polar	33892256
(R)-alpha-Methylhistamine,2TBDMS,isomer #2	CC(CC1=CN=C[NH]1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2050.5	Standard polar	33892256
(R)-alpha-Methylhistamine,3TBDMS,isomer #1	CC(CC1=CN=CN1[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2471.8	Semi standard non polar	33892256
(R)-alpha-Methylhistamine,3TBDMS,isomer #1	CC(CC1=CN=CN1[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2403.1	Standard non polar	33892256
(R)-alpha-Methylhistamine,3TBDMS,isomer #1	CC(CC1=CN=CN1[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2100.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-alpha-Methylhistamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-000x-9200000000-70b0b40b472e0dde1bd1	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-alpha-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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-alpha-Methylhistamine 10V, Positive-QTOF	splash10-0a4i-0900000000-d676ce468826ebee4e51	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-alpha-Methylhistamine 20V, Positive-QTOF	splash10-0a59-4900000000-11c85f73b47bebfca37f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-alpha-Methylhistamine 40V, Positive-QTOF	splash10-0f8c-9000000000-c40a45bc2e46ce61279a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-alpha-Methylhistamine 10V, Negative-QTOF	splash10-001i-9300000000-cc0d9983cc52c9eb8e29	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-alpha-Methylhistamine 20V, Negative-QTOF	splash10-053u-9500000000-54606326c1180cb8bba2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-alpha-Methylhistamine 40V, Negative-QTOF	splash10-014l-9000000000-84edaaeba68abc27f518	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3489

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Alpha-Methylhistamine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

74759

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for (R)-alpha-Methylhistamine (HMDB0243669)

MOL for HMDB0243669 ((R)-alpha-Methylhistamine)

3D MOL for HMDB0243669 ((R)-alpha-Methylhistamine)

3D SDF for HMDB0243669 ((R)-alpha-Methylhistamine)

3D-SDF for HMDB0243669 ((R)-alpha-Methylhistamine)

PDB for HMDB0243669 ((R)-alpha-Methylhistamine)

3D PDB for HMDB0243669 ((R)-alpha-Methylhistamine)

SMILES for HMDB0243669 ((R)-alpha-Methylhistamine)

INCHI for HMDB0243669 ((R)-alpha-Methylhistamine)

Structure for HMDB0243669 ((R)-alpha-Methylhistamine)

3D Structure for HMDB0243669 ((R)-alpha-Methylhistamine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra