T-HCA

T-HCA
Clinical data
Other names	trans-4-hydroxycrotonic acid
Identifiers
	IUPAC name (2E)-4-hydroxybut-2-enoic acid;
CAS Number	24587-49-3 ;
PubChem CID	6155526;
ChemSpider	4825947 ;
ChEMBL	ChEMBL507046 ;
Chemical and physical data
Formula	C4H6O3
Molar mass	102.09 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	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+ ; Key:RMQJECWPWQIIPW-OWOJBTEDSA-N ;
	(what is this?) (verify)

T-HCA, or trans-4-hydroxycrotonic acid, is a drug used in scientific research. It is structurally related to GHB and binds to the GHB receptor with 4-fold higher affinity than GHB itself,^[1] but is not an agonist for the primary sedative target of GHB, the GABA_B receptor, and so does not produce sedative effects, instead causing convulsions thought to be mediated through increased glutamate release.^[2] It may also be naturally produced in the mammalian CNS and is suspected to be an endogenous ligand for the GHB receptor.^[3]

References

^ Wellendorph P, Høg S, Greenwood JR, de Lichtenberg A, Nielsen B, Frølund B, Brehm L, Clausen RP, Bräuner-Osborne H (2005). "Novel Cyclic γ-Hydroxybutyrate (GHB) Analogs with High Affinity and Stereoselectivity of Binding to GHB Sites in Rat Brain" (pdf). The Journal of Pharmacology and Experimental Therapeutics. 315 (1): 346–351. doi:10.1124/jpet.105.090472. PMID 16014570.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ Castelli MP, Ferraro L, Mocci I; et al. (2003). "Selective γ-hydroxybutyric acid receptor ligands increase extracellular glutamate in the hippocampus, but fail to activate G protein and to produce the sedative/hypnotic effect of γ-hydroxybutyric acid". Journal of Neurochemistry. 87 (3): 722–732. doi:10.1046/j.1471-4159.2003.02037.x. PMID 14535954. {{cite journal}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: authors list (link)
^ Vayer P, Dessort D, Bourguignon JJ, Wermuth CG, Mandel P, Maitre M (1985). "Natural occurrence of trans-γ hydroxycrotonic acid in rat brain". Biochemical Pharmacology. 34 (13): 2401–2404. doi:10.1016/0006-2952(85)90804-4. PMID 4015683.{{cite journal}}: CS1 maint: multiple names: authors list (link)

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[1] Wellendorph P, Høg S, Greenwood JR, de Lichtenberg A, Nielsen B, Frølund B, Brehm L, Clausen RP, Bräuner-Osborne H (2005). "Novel Cyclic γ-Hydroxybutyrate (GHB) Analogs with High Affinity and Stereoselectivity of Binding to GHB Sites in Rat Brain" (pdf). The Journal of Pharmacology and Experimental Therapeutics. 315 (1): 346–351. doi:10.1124/jpet.105.090472. PMID 16014570.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[nsngtu-2] Castelli MP, Ferraro L, Mocci I; et al. (2003). "Selective γ-hydroxybutyric acid receptor ligands increase extracellular glutamate in the hippocampus, but fail to activate G protein and to produce the sedative/hypnotic effect of γ-hydroxybutyric acid". Journal of Neurochemistry. 87 (3): 722–732. doi:10.1046/j.1471-4159.2003.02037.x. PMID 14535954. {{cite journal}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: authors list (link)

[3] Vayer P, Dessort D, Bourguignon JJ, Wermuth CG, Mandel P, Maitre M (1985). "Natural occurrence of trans-γ hydroxycrotonic acid in rat brain". Biochemical Pharmacology. 34 (13): 2401–2404. doi:10.1016/0006-2952(85)90804-4. PMID 4015683.{{cite journal}}: CS1 maint: multiple names: authors list (link)

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[2]

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See also

References