HOCPCA | CAS#867178-11-8 | GHB ligand

MedKoo Cat#: 562419 | Name: HOCPCA

Description:

WARNING: This product is for research use only, not for human or veterinary use.

HOCPCA is a potent and selective ligand for the GHB binding sites. It acts by binding with 27 times better affinity than GHB itself and crossing the blood brain barrier in vitro and in vivo.

Chemical Structure

HOCPCA

CAS#867178-11-8

Theoretical Analysis

MedKoo Cat#: 562419

Name: HOCPCA

CAS#: 867178-11-8

Chemical Formula: C6H8O3

Exact Mass: 128.0473

Molecular Weight: 128.12

Elemental Analysis: C, 56.25; H, 6.29; O, 37.46

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

HOCPCA;

IUPAC/Chemical Name

3-Hydroxycyclopent-1-enecarboxylic acid

InChi Key

VKJGQKRRULDFCI-UHFFFAOYSA-N

InChi Code

InChI=1S/C6H8O3/c7-5-2-1-4(3-5)6(8)9/h3,5,7H,1-2H2,(H,8,9)

SMILES Code

OC1C=C(C(O)=O)CC1

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 128.12 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Krall J, Jensen CH, Bavo F, Falk-Petersen CB, Haugaard AS, Vogensen SB, Tian Y, Nittegaard-Nielsen M, Sigurdardóttir SB, Kehler J, Kongstad KT, Gloriam DE, Clausen RP, Harpsøe K, Wellendorph P, Frølund B. Molecular Hybridization of Potent and Selective γ-Hydroxybutyric Acid (GHB) Ligands: Design, Synthesis, Binding Studies, and Molecular Modeling of Novel 3-Hydroxycyclopent-1-enecarboxylic Acid (HOCPCA) and trans-γ-Hydroxycrotonic Acid (T-HCA) Analogs. J Med Chem. 2017 Nov 9;60(21):9022-9039. doi: 10.1021/acs.jmedchem.7b01351. Epub 2017 Oct 30. PubMed PMID: 29028338. 2: Jensen CH, Hansen HD, Bay T, Vogensen SB, Lehel S, Thiesen L, Bundgaard C, Clausen RP, Knudsen GM, Herth MM, Wellendorph P, Frølund B. Radiosynthesis and Evaluation of [(11)C]3-Hydroxycyclopent-1-enecarboxylic Acid as Potential PET Ligand for the High-Affinity γ-Hydroxybutyric Acid Binding Sites. ACS Chem Neurosci. 2017 Jan 18;8(1):22-27. doi: 10.1021/acschemneuro.6b00335. Epub 2016 Nov 17. PubMed PMID: 28095676. 3: Klein AB, Bay T, Villumsen IS, Falk-Petersen CB, Marek A, Frølund B, Clausen RP, Hansen HD, Knudsen GM, Wellendorph P. Autoradiographic imaging and quantification of the high-affinity GHB binding sites in rodent brain using (3)H-HOCPCA. Neurochem Int. 2016 Nov;100:138-145. doi: 10.1016/j.neuint.2016.09.002. Epub 2016 Sep 8. PubMed PMID: 27615059. 4: Marek A, Pedersen MH, Vogensen SB, Clausen RP, Frølund B, Elbert T. The labeling of unsaturated γ-hydroxybutyric acid by heavy isotopes of hydrogen: iridium complex-mediated H/D exchange by C─H bond activation vs reduction by boro-deuterides/tritides. J Labelled Comp Radiopharm. 2016 Oct;59(12):476-483. doi: 10.1002/jlcr.3432. Epub 2016 Sep 4. PubMed PMID: 27593893. 5: Thiesen L, Kehler J, Clausen RP, Frølund B, Bundgaard C, Wellendorph P. In Vitro and In Vivo Evidence for Active Brain Uptake of the GHB Analog HOCPCA by the Monocarboxylate Transporter Subtype 1. J Pharmacol Exp Ther. 2015 Aug;354(2):166-74. doi: 10.1124/jpet.115.224543. Epub 2015 May 18. PubMed PMID: 25986445. 6: Eghorn LF, Hoestgaard-Jensen K, Kongstad KT, Bay T, Higgins D, Frølund B, Wellendorph P. Positive allosteric modulation of the GHB high-affinity binding site by the GABAA receptor modulator monastrol and the flavonoid catechin. Eur J Pharmacol. 2014 Oct 5;740:570-7. doi: 10.1016/j.ejphar.2014.06.028. Epub 2014 Jun 25. PubMed PMID: 24973695. 7: Bay T, Eghorn LF, Klein AB, Wellendorph P. GHB receptor targets in the CNS: focus on high-affinity binding sites. Biochem Pharmacol. 2014 Jan 15;87(2):220-8. doi: 10.1016/j.bcp.2013.10.028. Epub 2013 Nov 20. Review. PubMed PMID: 24269284. 8: Vogensen SB, Marek A, Bay T, Wellendorph P, Kehler J, Bundgaard C, Frølund B, Pedersen MH, Clausen RP. New synthesis and tritium labeling of a selective ligand for studying high-affinity γ-hydroxybutyrate (GHB) binding sites. J Med Chem. 2013 Oct 24;56(20):8201-5. doi: 10.1021/jm4011719. Epub 2013 Oct 4. PubMed PMID: 24053696; PubMed Central PMCID: PMC3888956. 9: Kohlmeier KA, Vardar B, Christensen MH. γ-Hydroxybutyric acid induces actions via the GABAB receptor in arousal and motor control-related nuclei: implications for therapeutic actions in behavioral state disorders. Neuroscience. 2013 Sep 17;248:261-77. doi: 10.1016/j.neuroscience.2013.06.011. Epub 2013 Jun 18. PubMed PMID: 23791974. 10: Wellendorph P, Høg S, Greenwood JR, de Lichtenberg A, Nielsen B, Frølund B, Brehm L, Clausen RP, Bräuner-Osborne H. Novel cyclic gamma-hydroxybutyrate (GHB) analogs with high affinity and stereoselectivity of binding to GHB sites in rat brain. J Pharmacol Exp Ther. 2005 Oct;315(1):346-51. Epub 2005 Jul 12. PubMed PMID: 16014570.