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T-HCA

Clinical data
Other names	trans-4-hydroxycrotonic acid
ATC code	None
Identifiers
IUPAC name (2E)-4-hydroxybut-2-enoic acid
CAS Number	24587-49-3
PubChem CID	6155526
ChemSpider	4825947
UNII	NTM454U33F
ChEMBL	ChEMBL507046
CompTox Dashboard (EPA)	DTXSID901027169
Chemical and physical data
Formula	C4H6O3
Molar mass	102.089 g·mol
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
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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. T-HCA has been shown to cause receptor activation-evoked increases in extracellular glutamate concentrations, notably in the hippocampus.

See also

• HOCPCA
• γ-Crotonolactone

References

1. ^ Tunnicliff G, Cash CD (2 September 2003). Gamma-Hydroxybutyrate: Pharmacological and Functional Aspects. CRC Press. pp. 24, 104. ISBN 978-0-203-30099-2.
2. Quang LS, Desai MC, Kraner JC, Shannon MW, Woolf AD, Maher TJ (June 2002). "Enzyme and receptor antagonists for preventing toxicity from the gamma-hydroxybutyric acid precursor 1,4-butanediol in CD-1 mice". Annals of the New York Academy of Sciences. 965 (1): 461–472. Bibcode:2002NYASA.965..461Q. doi:10.1111/j.1749-6632.2002.tb04187.x. PMID 12105121. S2CID 25644267.
3. ^ Bourguignon JJ, Schoenfelder A, Schmitt M, Wermuth CG, Hechler V, Charlier B, Maitre M (May 1988). "Analogues of gamma-hydroxybutyric acid. Synthesis and binding studies". Journal of Medicinal Chemistry. 31 (5): 893–897. doi:10.1021/jm00400a001. PMID 3361576.
4. Maher TJ (24 January 2012). "Amino Acid Neurotransmitters in the Central Nervous System". In Lemke TL, Williams DA (eds.). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 414–. ISBN 978-1-60913-345-0.
5. Vayer P, Dessort D, Bourguignon JJ, Wermuth CG, Mandel P, Maitre M (July 1985). "Natural occurrence of trans-gamma hydroxycrotonic acid in rat brain". Biochemical Pharmacology. 34 (13): 2401–2404. doi:10.1016/0006-2952(85)90804-4. PMID 4015683.
6. Wellendorph P, Høg S, Greenwood JR, de Lichtenberg A, Nielsen B, Frølund B, et al. (October 2005). "Novel cyclic gamma-hydroxybutyrate (GHB) analogs with high affinity and stereoselectivity of binding to GHB sites in rat brain". The Journal of Pharmacology and Experimental Therapeutics. 315 (1): 346–351. doi:10.1124/jpet.105.090472. PMID 16014570. S2CID 10332754.
7. Patrylo PR (27 May 2009). "Epilepsy and Seizure Susceptibility in the Aging Brain". In Schwartzkron PD (ed.). Encyclopedia of Basic Epilepsy Research. Academic Press. pp. 44–. ISBN 978-0-12-373961-2.
8. ^ Castelli MP, Ferraro L, Mocci I, Carta F, Carai MA, Antonelli T, et al. (November 2003). "Selective gamma-hydroxybutyric acid receptor ligands increase extracellular glutamate in the hippocampus, but fail to activate G protein and to produce the sedative/hypnotic effect of gamma-hydroxybutyric acid". Journal of Neurochemistry. 87 (3): 722–732. doi:10.1046/j.1471-4159.2003.02037.x. PMID 14535954. S2CID 82175813.

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