Basic information
- Standard SMILES
O=C(O)C1=CCCNC1- InChIKey
QTDZOWFRBNTPQR-UHFFFAOYSA-N- Molecular formula
- C6H9NO2
- Average molar mass
- 127.14 g/mol
- Monoisotopic mass
- 127.06332853
Overview
Guvacine is a alpha,beta-unsaturated monocarboxylic acid that is nicotinic acid which has been hydrogenated at the 1-2 and 5-6 positions of the pyridine ring. It has a role as a plant metabolite and a GABA reuptake inhibitor. It is a pyridine alkaloid, a tetrahydropyridine, a beta-amino acid, a secondary amino compound and an alpha,beta-unsaturated monocarboxylic acid.
Names & identifiers
- Preferred name
- Guvacine
- IUPAC
- 1,2,3,6-tetrahydropyridine-5-carboxylic acid
- English name
- Guvacine
- Molecular formula
- C6H9NO2
- Molecular weight
- 127.14
Names & synonyms
Guvacine498-96-41,2,5,6-tetrahydropyridine-3-carboxylic acid1,2,5,6-Tetrahydro-3-pyridinecarboxylic acid1,2,5,6-Tetrahydronicotinic acid1,2,3,6-tetrahydropyridine-5-carboxylic acidCHEBI:557641538P325KDTXSID50871702RefChem:783281DTXCID808193391,2,3,6-tetrahydropyridin-1-ium-5-carboxylate
Show more names
GUVACINE-HCL3-Pyridinecarboxylic acid, 1,2,5,6-tetrahydro-1,2,5,6-TETRAHYDROPYRIDINE-3-CARBOXYLIC ACID HYDROCHLORIDE1,2,5,6-tetrahydropyridine-3-carboxylic acid(SALTDATA: HCl)
1,2,5,6-Tetrahydro-pyridine-3-carboxylic acidMFCD01365700MLS000859975SMR000326834UNII-41538P325KSpectrum_001426Tocris-0234SpecPlus_000808
Database identifiers
- CAS
498-96-4- PubChem CID
- 3532
- DTXSID
DTXSID50871702- ChEMBL
CHEMBL76768- ChEBI
CHEBI:5576- UNII
- 41538P325K
- Nikkaji
- J11.591F
Properties
Computed structural properties
- XLogP
- -2.5
- Topological polar surface area
- 49.3 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 1
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 151
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
SolubilitySoluble in water, and almost insoluble in 100% alcohol, ether, chloroform, and benzene.
Physicochemical properties
- Melting point
- 295 °C · 295°C (rough estimate)
- Boiling point
- 235.91 °C · 235.91°C (rough estimate)
- Density
- 1.1931 · 1.1931 (rough estimate)
- refractive index
- 1.4645 · 1.4645 (estimate)
- storage temp.
- Store at RT
- solubility
- 2 O: · H2O: soluble
- form
- solid
- pka
- 3.61 · 3.61±0.20(Predicted)
- color
- white
- InChI
- InChI=1S/C6H9NO2/c8-6(9)5-2-1-3-7-4-5/h2,7H,1,3-4H2,(H,8,9)
- InChIKey
- QTDZOWFRBNTPQR-UHFFFAOYSA-N
- SMILES
- C1NCCC=C1C(O)=O
- CAS DataBase Reference
- 498 · 498-96-4
- FDA UNII
- 41538 P325K · 41538P325K
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36
- WGK Germany
- 3 · 3
- HazardClass
- IRRITANT
Safety & regulation
Safety data
- wgk
- 3
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 26-36
- hazard_class
- IRRITANT
Chemistry & industry
Pharmacology
PharmacodynamicsExperimental studies are still being investigated to determine all of the physiological effects of guvacine.
Mechanism of Action
Experimental studies are still being investigated to determine the exact mechanisms of action of guvacine. What is known is that guvacine binds selectively to presynaptic GABA reuptake transporters and prevents the reuptake of GABA, but has no affinity for GABA postsynaptic receptors.
Applications
UsesGuvacine Hydrochloride is a GABA uptake inhibitor (hGABA T-1, rGABA T-2, hGABA T-3 and hBGT-1) (1,2,3). Gamma-Aminobutyric acid (GABA) is the major inhibitory neurotransmitter in the mammalian brain (4). Guvacine Hydrochloride may be useful for treating neuropsychiatric disorders.
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Additional notes
DefinitionChEBI: A alpha,beta-unsaturated monocarboxylic acid that is nicotinic acid which has been hydrogenated at the 1-2 and 5-6 positions of the pyridine ring.
Related reactions
1 records
Linked notes
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