T-HCA

T-HCA
Clinical data
Other namestrans-4-hydroxycrotonic acid
ATC code
  • None
Identifiers
  • (2E)-4-hydroxybut-2-enoic acid
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC4H6O3
Molar mass102.089 g·mol−1
3D model (JSmol)
  • O=C(O)\C=C\CO
  • 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 GABAB receptor. Because of this, T-HCA does not produce sedation. T-HCA has been shown to cause receptor activation-evoked increases in extracellular glutamate concentrations, notably in the hippocampus.