(2S)-2-ammonio-3-(1H-imidazol-4-yl)propanoate
Basic information
- CAS
71-00-1- Standard SMILES
[NH3+][C@@H](Cc1cnc[nH]1)C(=O)[O-]- InChIKey
HNDVDQJCIGZPNO-YFKPBYRVSA-N- Molecular formula
- C6H9N3O2
- Average molar mass
- 155.15 g/mol
- Monoisotopic mass
- 155.06947654
Overview
L-histidine zwitterion is zwitterionic form of L-histidine having an anionic carboxy group and a protonated alpha-amino group. It is an amino-acid zwitterion and a polar amino acid zwitterion. It is a tautomer of a L-histidine.
Names & identifiers
- Preferred name
- (2S)-2-ammonio-3-(1H-imidazol-4-yl)propanoate
- IUPAC
- (2S)-2-azaniumyl-3-(1H-imidazol-5-yl)propanoate
- English name
- L-Histidine
- Molecular formula
- C6H9N3O2
- Molecular weight
- 155.15
Names & synonyms
L-histidine zwitterion2q2cCHEBI:57595alpha-amino-4-imidazoleproprionic acid(2S)-2-ammonio-3-(1H-imidazol-4-yl)propanoate(2S)-2-azaniumyl-3-(1H-imidazol-4-yl)propanoateHISHISTIDINEH-HIS-OHL-HISL-His-OHL-HISTIDINE BASE
Show more names
HistidinL-Histidin(S)-2-aMino-3-(1H-iMidazol-4-yl)propanoic acidH-L-HIS-OH
Database identifiers
- CAS
71-00-1- PubChem CID
- 6971009
- ChEBI
CHEBI:57595
Properties
Computed structural properties
- XLogP
- -2.6
- Topological polar surface area
- 96.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 145
Experimental & physicochemical properties
LogP-3.32
Solubility45.6 mg/mL
Melting Point287 °C
Physical DescriptionSolid
Dissociation Constants2.76 (at 0 °C)
Physicochemical properties
- Melting point
- 282 °C · 282 °C (dec.)(lit.)
- alpha
- 12.4 · 12.4 º (c=11,6N HCl)
- Boiling point
- 278.95 °C · 278.95°C (rough estimate)
- Density
- 1.3092 · 1.3092 (rough estimate)
- bulk density
- 430 kg/m3 · 430kg/m3
- refractive index
- 13 ° · 13 ° (C=11, 6mol/L HCl)
- FEMA
- 3694 · 3694 | L-HISTIDINE
- FLAVIS Number
- 17.008 · 17.008 | L-Histidine
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 10-23
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- MS3070000
- hs_code
- 29332990
- Toxicity
- LD50 orally in Rabbit: > 5110 mg/kg
- risk_code
- 22-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 24/25-36/37-26-22
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- REACH Registrations
- Active
- Precautionary statements
- P261-P280-P301+P312-P302+P352-P305+P351+P338
- Hazardous Substances Data
- 71-00-1(Hazardous Substances Data)
Chemistry & industry
Pharmacology
PharmacodynamicsIs found abundantly in hemoglobin; has been used in the treatment of rheumatoid arthritis, allergic diseases, ulcers and anemia. A deficiency can cause poor hearing.
Mechanism of Action
Since the actions of supplemental L-histidine are unclear, any postulated mechanism is entirely speculative. However, some facts are known about L-histidine and some of its metabolites, such as histamine and trans-urocanic acid, which suggest that supplemental L-histidine may one day be shown to have immunomodulatory and/or antioxidant activities. Low free histidine has been found in the serum of some rheumatoid arthritis patients. Serum concentrations of other amino acids have been found to be normal in these patients. L-histidine is an excellent chelating agent for such metals as copper, iron and zinc. Copper and iron participate in a reaction (Fenton reaction) that generates potent reactive oxygen species that could be destructive to tissues, including joints. L-histidine is the obligate precursor of histamine, which is produced via the decarboxylation of the amino acid. In experimental animals, tissue histamine levels increase as the amount of dietary L-histidine increases. It is likely that this would be the case in humans as well. Histamine is known to possess immunomodulatory and antioxidant activity. Suppressor T cells have H2 receptors, and histamine activates them. Promotion of suppressor T cell activity could be beneficial in rheumatoid arthritis. Further, histamine has been shown to down-regulate the production of reactive oxygen species in phagocytic cells, such as monocytes, by binding to the H2 receptors on these cells. Decreased reactive oxygen species production by phagocytes could play antioxidant, anti-inflammatory and immunomodulatory roles in such diseases as rheumatoid arthritis. This latter mechanism is the rationale for the use of histamine itself in several clinical trials studying histamine for the treatment of certain types of cancer and viral diseases. In these trials, down-regulation by histamine of reactive oxygen species formation appears to inhibit the suppression of natural killer (NK) cells and cytotoxic T lymphocytes, allowing these cells to be more effective in attacking cancer cells and virally infected cells.
Absorption, Distribution and ExcretionAbsorbed from the small intestine via an active transport mechanism requiring the presence of sodium.
Related reactions
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Compound notes
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