Basic information
- Standard SMILES
O=C(O)c1cnccn1- InChIKey
NIPZZXUFJPQHNH-UHFFFAOYSA-N- Molecular formula
- C5H4N2O2
- Average molar mass
- 124.1 g/mol
- Monoisotopic mass
- 124.02727737
Overview
Pyrazine-2-carboxylic acid is the parent compound of the class of pyrazinecarboxylic acids, that is pyrazine bearing a single carboxy substituent. The active metabolite of the antitubercular drug pyrazinamide. It has a role as an antitubercular agent and a drug metabolite. It is a conjugate acid of a pyrazine-2-carboxylate.
Names & identifiers
- Preferred name
- 2-Pyrazinecarboxylic acid
- IUPAC
- pyrazine-2-carboxylic acid
- English name
- 2-Pyrazinecarboxylic acid
- Molecular formula
- C5H4N2O2
- Molecular weight
- 124.1
Names & synonyms
Pyrazine-2-carboxylic acid2-Pyrazinecarboxylic acid98-97-5pyrazinoic acidpyrazinecarboxylic acidParadiazinecarboxylic acidpyrazinemonocarboxylic acidNSC-13146CHEBI:71311DTXSID302433672WB23298SPRefChem:177455
Show more names
NSC 13146NSC 27192NSC 13146-d3NSC 27192-d3Pyrazoic acidPyrazinecarboxyL
CHEBI:48345DTXCID30165858202-718-1Pyrazinic acid2-Carboxypyrazine2-Pyrazine carboxylic acid2-Pyrazinoic acidPiazinecarboxylic acid
Database identifiers
- CAS
98-97-5- PubChem CID
- 1047
- DTXSID
DTXSID30243367- ChEMBL
CHEMBL613- ChEBI
CHEBI:71311- UNII
- 2WB23298SP
- EC Number
- 202-718-1
- Nikkaji
- J11.623H
Properties
Computed structural properties
- XLogP
- 0.1
- Topological polar surface area
- 63.1 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 1
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 116
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Pyrazines
SpringerMaterials Properties15N nuclear magnetic resonance spectrum
Physical DescriptionWhite solid; [Merck Index] White or off-white powder; [Alfa Aesar MSDS]
Physicochemical properties
- Melting point
- 222 · 222-225 °C (dec.)(lit.)
- Boiling point
- 230.85 °C · 230.85°C (rough estimate)
- Density
- 1.4317 · 1.4317 (rough estimate)
- vapor pressure
- 0.011 Pa · 0.011Pa at 25℃
- refractive index
- 1.48 · 1.4800 (estimate)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- DMSO (Slightly), Methanol (Slightly, Heated)
- form
- Crystalline Powder
- pka
- pK (25°) 2.92
- color
- White to off-white
- Water Solubility
- SOLUBLE IN COLD WATER
- Merck
- 14 · 14,8970
- BRN
- 112305 · 112305
- InChI
- 1S/C5H4N2O2/c8-5(9)4-3-6-1-2-7-4/h1-3H,(H,8,9)
- InChIKey
- NIPZZXUFJPQHNH-UHFFFAOYSA-N
- SMILES
- OC(=O)c1cnccn1
- LogP
- -0.18 · -0.18
- CAS DataBase Reference
- 98 · 98-97-5(CAS DataBase Reference)
- FDA UNII
- 2 WB23298SP · 2WB23298SP
- NIST Chemistry Reference
- Pyrazinoic acid(98-97-5)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P305+P351+P338
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Hazard Codes
- Xi,C,F
- Risk Statements
- 11 · 11-34
- Safety Statements
- 22 · 22-24/25-45-36/37/39-26-16
- WGK Germany
- 3 · 3
- HS Code
- 29339990 · 29339990
- Storage Class
- 11 · 11 - Combustible Solids
- REACH Registrations
- Inactive
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 82.4% (14 of 17) of all reports.
Warning
H315 (17.6%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 17 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Pyrazinecarboxylic acid
Status: Cease Manufacture Update: 28-06-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/19785
Pyrazinecarboxylic acid: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryMay cause irritation; [Alfa Aesar MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (17.6%)
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- hs_code
- 29339990
- risk_code
- 11-34
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi,C,F
- safety_code
- 22-24/25-45-36/37/39-26-16
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- REACH Registrations
- Inactive
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Pharmacology
Tissue LocationsKidney
Cellular LocationsCytoplasm
Applications
UsesPyrazinecarboxylic Acid is a very potent urate retaining drug. Pyrazinecarboxylic Acid is a metabolite of the antibacterial agent Pyrazinamide (P840600).
UsesLabelled analogue of Pyrazinecarboxylic Acid, a very potent urate retaining drug. Pyrazinecarboxylic Acid is a metabolite of the antibacterial agent Pyrazinamide (P840600).
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionChEBI: The parent compound of the class of pyrazinecarboxylic acids, that is pyrazine bearing a single carboxy substituent. The active metabolite of the antitubercular drug pyrazinamide.
Related reactions
926 records
Linked notes
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