Showing Metabocard for agmatine (BASm0003233)
| Common Name | Agmatine |
|---|---|
| Description | Agmatine ((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. |
| Structure | |
| Molecular Formula | C5H14N4 |
| Average Mass | 130.19150 |
| Monoisotopic Mass | 130.12185 |
| IUPAC Name | 1-(4-aminobutyl)guanidine |
| Traditional Name | Agmatine |
| CAS Registry Number | 306-60-5 |
| SMILES | NC(=[NH2+])NCCCC[NH3+] |
| InChI Identifier | InChI=1S/C5H14N4/c6-3-1-2-4-9-5(7)8/h1-4,6H2,(H4,7,8,9) |
| InChI Key | QYPPJABKJHAVHS-UHFFFAOYSA-N |
| CHEBI ID | CHEBI:58145 |
| HMDB ID | HMDB0001432 |
| State | Solid |
| Water Solubility | 3.61e+00 g/l |
| logP | -1.01 |
| logS | -1.56 |
| pKa (Strongest Acidic) | Not Available |
| pKa (Strongest Basic) | 12.61 |
| Hydrogen Acceptor Count | 4 |
| Hydrogen Donor Count | 4 |
| Polar Surface Area | 87.92 Ų |
| Rotatable Bond Count | 4 |
| Physiological Charge | 2 |
| Formal Charge | 0 |
| Refractivity | 48.09 m³·mol⁻¹ |
| Polarizability | 15.01 |