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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:04:40 UTC
HMDB IDHMDB01432
Secondary Accession Numbers
  • HMDB60259
Metabolite Identification
Common NameAgmatine
DescriptionAgmatine ((4-aminobutyl)guanidine, NH2-CH2-CH2-CH2-CH2-NH-C(-NH2)(=NH)) is the decarboxylation product of the amino acid arginine and is an intermediate in polyamine biosynthesis. It is a putative neurotransmitter. It is synthesized in the brain, stored in synaptic vesicles, accumulated by uptake, released by membrane depolarization, and inactivated by agmatinase. Agmatine binds to 2-adrenergic receptor and imidazoline binding sites, and blocks NMDA receptors and other cation ligand-gated channels. Agmatine inhibits nitric oxide synthase (NOS), and induces the release of some peptide hormones. Treatment with exogenous agmatine exerts neuroprotective effects in animal models of neurotrauma. -- Wikipedia.
Structure
Thumb
Synonyms
ValueSource
(4-Aminobutyl) guanidineChEBI
(4-Aminobutyl)guanidineChEBI
N-(4-Aminobutyl)guanidineChEBI
(4-Aminobutyl)-guanidineHMDB
1-(4-Aminobutyl)guanidineHMDB
1-amino-4-GuanidinobutaneHMDB
1-amino-4-GuanidobutaneHMDB
4-guanidino-1-ButanamineHMDB
AgmatiniumHMDB
ArgmatineHMDB
N-(Aminoiminomethyl)-1,4-butanediamineHMDB
N-4-AminobutylguanidineHMDB
Chemical FormulaC5H14N4
Average Molecular Weight130.1915
Monoisotopic Molecular Weight130.121846468
IUPAC Name1-(4-aminobutyl)guanidine
Traditional Nameagmatine
CAS Registry Number306-60-5
SMILES
NCCCCNC(N)=N
InChI Identifier
InChI=1S/C5H14N4/c6-3-1-2-4-9-5(7)8/h1-4,6H2,(H4,7,8,9)
InChI KeyInChIKey=QYPPJABKJHAVHS-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as guanidines. These are compounds containing a guanidine moiety, with the general structure (R1R2N)(R3R4N)C=N-R5.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassGuanidines
Sub ClassNot Available
Direct ParentGuanidines
Alternative Parents
Substituents
  • Guanidine
  • Carboximidamide
  • Hydrocarbon derivative
  • Primary amine
  • Primary aliphatic amine
  • Imine
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Arginine and proline metabolism
ApplicationNot Available
Cellular locations
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.61 mg/mLALOGPS
logP-1ALOGPS
logP-1.2ChemAxon
logS-1.6ALOGPS
pKa (Strongest Basic)12.61ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area87.92 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity48.09 m3·mol-1ChemAxon
Polarizability15.01 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0002-0900000000-a9f6a71ff1ddda580ea9View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-00di-1910000000-4c97cf5e84d752009d1aView in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00di-1910000000-de398de0f062b85c083cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00e9-9700000000-dcb266f2466b6490a487View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9000000000-e4747ffbbb1c0aa02f4eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-9000000000-e97e998997ab8bfcedb5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-001i-0900000000-4843789c1dd06e41493dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-9200000000-a6b84c1241179a3739f8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00di-9000000000-57f390519e8ddbcb80a8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00di-9000000000-e38858b8c1a4fb2a6b14View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-00di-9000000000-2e6fd942608b84941a7dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-001i-0900000000-075bad34dbbb7544e053View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00di-9600000000-368edccb095766335b38View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-3900000000-21dc8634e0e5c79fc825View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9300000000-55aa9e9ef7923b67457fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9000000000-ec5b24cf1199482a883dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-9500000000-f8e119f2ba53222591a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-c4883e27e32ef6874c13View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-2b9c32eb2684272e86a2View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Mitochondria
Biofluid Locations
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • Brain
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.310 +/- 0.0699 uMAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected and Quantified0.0232 +/- 0.0382 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.0403 +/- 0.0425 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.0578 +/- 0.0466 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.170 +/- 0.210 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified0.025 (0.02-0.03) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB008310
KNApSAcK IDC00001400
Chemspider ID194
KEGG Compound IDC00179
BioCyc IDAGMATHINE
BiGG ID34153
Wikipedia LinkAgmatine
NuGOwiki LinkHMDB01432
Metagene LinkHMDB01432
METLIN ID3523
PubChem Compound199
PDB IDAG2
ChEBI ID17431
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Halaris A, Piletz JE: Relevance of imidazoline receptors and agmatine to psychiatry: a decade of progress. Ann N Y Acad Sci. 2003 Dec;1009:1-20. [15028565 ]
  2. Feng Y, Halaris AE, Piletz JE: Determination of agmatine in brain and plasma using high-performance liquid chromatography with fluorescence detection. J Chromatogr B Biomed Sci Appl. 1997 Apr 11;691(2):277-86. [9174263 ]
  3. Atlas D: Molecular and physiological properties of clonidine-displacing substance. Ann N Y Acad Sci. 1995 Jul 12;763:314-24. [7677341 ]
  4. Zhao S, Wang B, Yuan H, Xiao D: Determination of agmatine in biological samples by capillary electrophoresis with optical fiber light-emitting-diode-induced fluorescence detection. J Chromatogr A. 2006 Aug 4;1123(1):138-41. Epub 2006 Jul 3. [16820162 ]
  5. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 Mar 3. doi: 10.1038/nbt.2488. [23455439 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Decarboxylates L-arginine to agmatine. Truncated splice isoforms probably lack activity.
Gene Name:
ADC
Uniprot ID:
Q96A70
Molecular weight:
49979.185
Reactions
L-Arginine → Agmatine + CO(2)details
L-Arginine → Agmatine + Carbon dioxidedetails
General function:
Involved in agmatinase activity
Specific function:
Not Available
Gene Name:
AGMAT
Uniprot ID:
Q9BSE5
Molecular weight:
37660.065
Reactions
Agmatine + Water → Putrescine + Ureadetails
General function:
Involved in transporter activity
Specific function:
Probably transports organic cations. Appears not to be the agmatine transporter
Gene Name:
SLC22A15
Uniprot ID:
Q8IZD6
Molecular weight:
60539.5