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MedKoo Cat#: 558259 | Name: ABP688

Description:

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

ABP688 is a noncompetitive and highly selective antagonist for the metabotropic glutamate receptor subtype (mGluR5). [11C]-ABP688 may be used for imaging purposes using PET.

Chemical Structure

ABP688
ABP688
CAS#1224977-89-2

Theoretical Analysis

MedKoo Cat#: 558259

Name: ABP688

CAS#: 1224977-89-2

Chemical Formula: C1411CH16N2O

Exact Mass: 239.1377

Molecular Weight: 239.31

Elemental Analysis: C, 74.87; H, 6.74; N, 11.71; O, 6.69

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.
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Related CAS #
No Data
Synonym
ABP688; ABP-688; ABP 688.
IUPAC/Chemical Name
(E)-3-((6-methylpyridin-2-yl)ethynyl)cyclohex-2-en-1-one O-methyl oxime
InChi Key
CNNZLFXCUQLKOB-BMRADRMJSA-N
InChi Code
InChI=1S/C15H16N2O/c1-12-5-3-7-14(16-12)10-9-13-6-4-8-15(11-13)17-18-2/h3,5,7,11H,4,6,8H2,1-2H3/b17-15+
SMILES Code
CC1=CC=CC(C#CC(CCC/2)=CC2=N\OC)=N1
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

Preparing Stock Solutions

The following data is based on the product molecular weight 239.31 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.

Recalculate based on batch purity %
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: Bdair H, Tsai IH, Smart K, Benkelfat C, Leyton M, Kostikov A. Radiosynthesis of the diastereomerically pure (E)-[11 C]ABP688. J Labelled Comp Radiopharm. 2019 Oct;62(12):860-864. doi: 10.1002/jlcr.3802. Epub 2019 Sep 18. PMID: 31418468. 2: Kawamura K, Yamasaki T, Kumata K, Furutsuka K, Takei M, Wakizaka H, Fujinaga M, Kariya K, Yui J, Hatori A, Xie L, Shimoda Y, Hashimoto H, Hayashi K, Zhang MR. Binding potential of (E)-[¹¹C]ABP688 to metabotropic glutamate receptor subtype 5 is decreased by the inclusion of its ¹¹C-labelled Z-isomer. Nucl Med Biol. 2014 Jan;41(1):17-23. doi: 10.1016/j.nucmedbio.2013.09.008. Epub 2013 Oct 8. PMID: 24183615. 3: Glorie D, Verhaeghe J, Miranda A, De Lombaerde S, Stroobants S, Staelens S. Quantification of Metabotropic Glutamate Receptor 5 Availability With Both [11C]ABP688 and [18F]FPEB Positron Emission Tomography in the Sapap3 Knockout Mouse Model for Obsessive-Compulsive-like Behavior. Biol Psychiatry Cogn Neurosci Neuroimaging. 2022 Jun;7(6):607-615. doi: 10.1016/j.bpsc.2021.11.010. Epub 2021 Nov 29. PMID: 34856382. 4: Smart K, Cox SML, Nagano-Saito A, Rosa-Neto P, Leyton M, Benkelfat C. Test- retest variability of [11 C]ABP688 estimates of metabotropic glutamate receptor subtype 5 availability in humans. Synapse. 2018 Sep;72(9):e22041. doi: 10.1002/syn.22041. Epub 2018 Jul 20. PMID: 29935121. 5: Bertoglio D, Kosten L, Verhaeghe J, Thomae D, Wyffels L, Stroobants S, Wityak J, Dominguez C, Mrzljak L, Staelens S. Longitudinal Characterization of mGluR5 Using 11C-ABP688 PET Imaging in the Q175 Mouse Model of Huntington Disease. J Nucl Med. 2018 Nov;59(11):1722-1727. doi: 10.2967/jnumed.118.210658. Epub 2018 May 24. PMID: 29794227. 6: Glorie D, Verhaeghe J, Miranda A, Kertesz I, Wyffels L, Stroobants S, Staelens S. Progression of obsessive compulsive disorder-like grooming in Sapap3 knockout mice: A longitudinal [11C]ABP688 PET study. Neuropharmacology. 2020 Oct 15;177:108160. doi: 10.1016/j.neuropharm.2020.108160. Epub 2020 May 23. PMID: 32454126. 7: Smart K, Cox SML, Scala SG, Tippler M, Jaworska N, Boivin M, Séguin JR, Benkelfat C, Leyton M. Sex differences in [11C]ABP688 binding: a positron emission tomography study of mGlu5 receptors. Eur J Nucl Med Mol Imaging. 2019 May;46(5):1179-1183. doi: 10.1007/s00259-018-4252-4. Epub 2019 Jan 9. PMID: 30627817; PMCID: PMC6451701. 8: Treyer V, Gietl AF, Suliman H, Gruber E, Meyer R, Buchmann A, Johayem A, Unschuld PG, Nitsch RM, Buck A, Ametamey SM, Hock C. Reduced uptake of [11C]-ABP688, a PET tracer for metabolic glutamate receptor 5 in hippocampus and amygdala in Alzheimer's dementia. Brain Behav. 2020 Jun;10(6):e01632. doi: 10.1002/brb3.1632. Epub 2020 Apr 18. PMID: 32304284; PMCID: PMC7303388. 9: DeLorenzo C, DellaGioia N, Bloch M, Sanacora G, Nabulsi N, Abdallah C, Yang J, Wen R, Mann JJ, Krystal JH, Parsey RV, Carson RE, Esterlis I. In vivo ketamine-induced changes in [¹¹C]ABP688 binding to metabotropic glutamate receptor subtype 5. Biol Psychiatry. 2015 Feb 1;77(3):266-275. doi: 10.1016/j.biopsych.2014.06.024. Epub 2014 Jul 10. PMID: 25156701; PMCID: PMC4277907. 10: Smart K, Cox SML, Kostikov A, Shalai A, Scala SG, Tippler M, Jaworska N, Boivin M, Séguin JR, Benkelfat C, Leyton M. Effect of (Z)-isomer content on [11C]ABP688 binding potential in humans. Eur J Nucl Med Mol Imaging. 2019 May;46(5):1175-1178. doi: 10.1007/s00259-018-4237-3. Epub 2019 Jan 3. PMID: 30607444. 11: Régio Brambilla C, Veselinović T, Rajkumar R, Mauler J, Matusch A, Ruch A, Orth L, Ramkiran S, Sbaihat H, Kaulen N, Khudeish NY, Wyss C, Heekeren K, Kawohl W, Rota Kops E, Tellmann L, Scheins J, Boers F, Neumaier B, Ermert J, Lang M, Stüsgen S, Herzog H, Langen KJ, Shah NJ, Lerche CW, Neuner I. mGluR5 binding changes during a mismatch negativity task in a multimodal protocol with [11C]ABP688 PET/MR-EEG. Transl Psychiatry. 2022 Jan 10;12(1):6. doi: 10.1038/s41398-021-01763-3. PMID: 35013095; PMCID: PMC8748790. 12: Ametamey SM, Kessler LJ, Honer M, Wyss MT, Buck A, Hintermann S, Auberson YP, Gasparini F, Schubiger PA. Radiosynthesis and preclinical evaluation of 11C-ABP688 as a probe for imaging the metabotropic glutamate receptor subtype 5. J Nucl Med. 2006 Apr;47(4):698-705. PMID: 16595505. 13: DuBois JM, Rousset OG, Rowley J, Porras-Betancourt M, Reader AJ, Labbe A, Massarweh G, Soucy JP, Rosa-Neto P, Kobayashi E. Characterization of age/sex and the regional distribution of mGluR5 availability in the healthy human brain measured by high-resolution [(11)C]ABP688 PET. Eur J Nucl Med Mol Imaging. 2016 Jan;43(1):152-162. doi: 10.1007/s00259-015-3167-6. Epub 2015 Aug 21. PMID: 26290423. 14: Verhaeghe J, Bertoglio D, Kosten L, Thomae D, Verhoye M, Van Der Linden A, Wyffels L, Stroobants S, Wityak J, Dominguez C, Mrzljak L, Staelens S. Noninvasive Relative Quantification of [11C]ABP688 PET Imaging in Mice Versus an Input Function Measured Over an Arteriovenous Shunt. Front Neurol. 2018 Jun 29;9:516. doi: 10.3389/fneur.2018.00516. PMID: 30013509; PMCID: PMC6036254. 15: Streffer J, Treyer V, Buck A, Ametamey SM, Blagoev M, Maguire RP, Gautier A, Auberson YP, Schmidt ME, Vranesic IT, Gomez-Mancilla B, Gasparini F. Regional brain mGlu5 receptor occupancy following single oral doses of mavoglurant as measured by [11C]-ABP688 PET imaging in healthy volunteers. Neuroimage. 2021 Apr 15;230:117785. doi: 10.1016/j.neuroimage.2021.117785. Epub 2021 Feb 2. PMID: 33545349. 16: Wyckhuys T, Verhaeghe J, Wyffels L, Langlois X, Schmidt M, Stroobants S, Staelens S. N-acetylcysteine- and MK-801-induced changes in glutamate levels do not affect in vivo binding of metabotropic glutamate 5 receptor radioligand 11C-ABP688 in rat brain. J Nucl Med. 2013 Nov;54(11):1954-61. doi: 10.2967/jnumed.113.121608. Epub 2013 Sep 19. PMID: 24050937. 17: Leung K. 3-(Pyridin-2-ylethynyl)-cyclohex-2-enone-O-[18F]fluoroethyl- oxime. 2007 Dec 3 [updated 2008 Jan 28]. In: Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004–2013. PMID: 20641843. 18: Kim SE, Joo YH, Son YD, Kim HK, Lee SY, Lee MW, Ido T, Kim JH. Association between human gray matter metabotropic glutamate receptor-5 availability in vivo and white matter properties: a [11C]ABP688 PET and diffusion tensor imaging study. Brain Struct Funct. 2020 Jul;225(6):1805-1816. doi: 10.1007/s00429-020-02094-7. Epub 2020 Jun 3. PMID: 32495131. 19: Choi H, Kim YK, Oh SW, Im HJ, Hwang DW, Kang H, Lee B, Lee YS, Jeong JM, Kim EE, Chung JK, Lee DS. In vivo imaging of mGluR5 changes during epileptogenesis using [11C]ABP688 PET in pilocarpine-induced epilepsy rat model. PLoS One. 2014 Mar 24;9(3):e92765. doi: 10.1371/journal.pone.0092765. PMID: 24663806; PMCID: PMC3963947. 20: Elmenhorst D, Aliaga A, Bauer A, Rosa-Neto P. Test-retest stability of cerebral mGluR₅ quantification using [¹¹C]ABP688 and positron emission tomography in rats. Synapse. 2012 Jun;66(6):552-60. doi: 10.1002/syn.21542. Epub 2012 Mar 16. PMID: 22290765.

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