T-HCA

T-HCA

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Systematic (IUPAC) name
(2E)-4-hydroxybut-2-enoic acid
Identifiers
CAS Number	24587-49-3 N
ATC code	None
PubChem	CID: 6155526
ChemSpider	4825947 Y
ChEMBL	CHEMBL507046 Y
Synonyms	trans-4-hydroxycrotonic acid
Chemical data
Formula	C4H6O3
Molecular mass	102.09 g/mol
SMILES O=C(O)\C=C\CO
InChI InChI=1S/C4H6O3/c5-3-1-2-4(6)7/h1-2,5H,3H2,(H,6,7)/b2-1+ Y Key:RMQJECWPWQIIPW-OWOJBTEDSA-N Y
NY (what is this?)  (verify)

trans-4-Hydroxycrotonic acid (T-HCA), also known as γ-hydroxycrotonic acid (GHC), is an agent used in scientific research to study the GHB receptor. It is an analogue of γ-hydroxybutyric acid (GHB), as well as an active metabolite of GHB. Similarly to GHB, T-HCA has been found to be endogenous to the rat central nervous system, and as a metabolite of GHB, is almost certain to be endogenous to humans as well. T-HCA binds to the high-affinity GHB receptor with 4-fold greater affinity than GHB itself, where it acts as an agonist, but does not bind to the low-affinity GHB binding site, the GABA_B receptor. Because of this, T-HCA does not produce sedation, and instead causes convulsions, which are thought to be caused by GHB receptor activation-evoked increases in extracellular glutamate concentrations, with one notable area where this occurs being the hippocampus.

See also

• HOCPCA
• γ-Crotonolactone