Gaboxadol HCl
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MedKoo CAT#: 525150

CAS#: 85118-33-8 (HCl)

Description: Gaboxadol, also known as THIP, OV-101; Lu-02-030; MK-0928; Lu-02030, is a GABA agonist. It is an inhibitor of GABA uptake systems. Gaboxadol can also be a non-opioid analgesic and a novel type of hypnotic.


Price and Availability

Size
Price

25mg
USD 230
Size
Price

Size
Price

Gaboxadol, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 525150
Name: Gaboxadol HCl
CAS#: 85118-33-8 (HCl)
Chemical Formula: C6H9ClN2O2
Exact Mass: 140.05858
Molecular Weight: 176.6
Elemental Analysis: C, 40.81; H, 5.14; Cl, 20.07; N, 15.86; O, 18.12


Synonym: Gaboxadol; OV-101; Lu-02-030; MK-0928; Lu-02030; OV-101; Lu02-030; MK0928; Lu02030. THIP

IUPAC/Chemical Name: 4,5,6,7-Tetrahydroisoxazolo(5,4-c)pyridin-3(2H)-one monohydrochloride

InChi Key: ZDZDSZQYRBZPNN-UHFFFAOYSA-N

InChi Code: InChI=1S/C6H8N2O2.ClH/c9-6-4-1-2-7-3-5(4)10-8-6;/h7H,1-3H2,(H,8,9);1H

SMILES Code: O=C1NOC2=C1CCNC2.[H]Cl


Technical Data

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).

Harmonized System Code:
293490


Additional Information

Related CAS#
CAS#64603-91-4 (Gaboxadol freebase)
CAS#85118-33-8 (Gaboxadol hydrochloride salt)
CAS#65202-63-3 (Gaboxadol hydrobromide salt)


References

1: Silverman NS, Popp S, Vialou V, Astafurov K, Nestler EJ, Dow-Edwards D. Effects of gaboxadol on the expression of cocaine sensitization in rats. Exp Clin Psychopharmacol. 2016 Apr;24(2):131-41. doi: 10.1037/pha0000069. Epub 2016 Feb 22. PubMed PMID: 26901591.

2: Zanettini C, Pressly JD, Ibarra MH, Smith KR, Gerak LR. Comparing the discriminative stimulus effects of modulators of GABAA receptors containing α4-δ subunits with those of gaboxadol in rats. Psychopharmacology (Berl). 2016 May;233(10):2005-13. doi: 10.1007/s00213-016-4243-8. Epub 2016 Feb 22. PubMed PMID: 26900079.

3: Kesisoglou F, Balakrishnan A, Manser K. Utility of PBPK Absorption Modeling to Guide Modified Release Formulation Development of Gaboxadol, a Highly Soluble Compound With Region-Dependent Absorption. J Pharm Sci. 2016 Feb;105(2):722-8. doi: 10.1002/jps.24674. Epub 2016 Jan 11. PubMed PMID: 26457884.

4: Ramaker MJ, Strong-Kaufman MN, Ford MM, Phillips TJ, Finn DA. Effect of nucleus accumbens shell infusions of ganaxolone or gaboxadol on ethanol consumption in mice. Psychopharmacology (Berl). 2015 Apr;232(8):1415-26. doi: 10.1007/s00213-014-3777-x. Epub 2014 Oct 25. PubMed PMID: 25342197; PubMed Central PMCID: PMC4412309.

5: Fritz BM, Boehm SL 2nd. Site-specific microinjection of Gaboxadol into the infralimbic cortex modulates ethanol intake in male C57BL/6J mice. Behav Brain Res. 2014 Oct 15;273:8-15. doi: 10.1016/j.bbr.2014.07.020. Epub 2014 Jul 18. PubMed PMID: 25043731; PubMed Central PMCID: PMC4152776.

6: Ramaker MJ, Ford MM, Phillips TJ, Finn DA. Differences in the reinstatement of ethanol seeking with ganaxolone and gaboxadol. Neuroscience. 2014 Jul 11;272:180-7. doi: 10.1016/j.neuroscience.2014.04.065. Epub 2014 May 9. PubMed PMID: 24814021; PubMed Central PMCID: PMC4122668.

7: Lopez de Diego H, Koradia V, Bond AD. Enantiotropically related polymorphs of gaboxadol hydrochloride. Acta Crystallogr C. 2013 Nov;69(Pt 11):1234-7. doi: 10.1107/S0108270113025961. Epub 2013 Oct 19. PubMed PMID: 24192165.

8: Broberg Ml, Holm R, Tønsberg H, Frølund S, Ewon KB, Nielsen Al, Brodin B, Jensen A, Kall MA, Christensen KV, Nielsen CU. Function and expression of the proton-coupled amino acid transporter PAT1 along the rat gastrointestinal tract: implications for intestinal absorption of gaboxadol. Br J Pharmacol. 2012 Oct;167(3):654-65. doi: 10.1111/j.1476-5381.2012.02030.x. PubMed PMID: 22577815; PubMed Central PMCID: PMC3449268.

9: Vashchinkina E, Panhelainen A, Vekovischeva OY, Aitta-aho T, Ebert B, Ator NA, Korpi ER. GABA site agonist gaboxadol induces addiction-predicting persistent changes in ventral tegmental area dopamine neurons but is not rewarding in mice or baboons. J Neurosci. 2012 Apr 11;32(15):5310-20. doi: 10.1523/JNEUROSCI.4697-11.2012. PubMed PMID: 22496576.

10: Christensen T, Bétry C, Mnie-Filali O, Etievant A, Ebert B, Haddjeri N, Wiborg O. Synergistic antidepressant-like action of gaboxadol and escitalopram. Eur Neuropsychopharmacol. 2012 Oct;22(10):751-60. doi: 10.1016/j.euroneuro.2012.02.001. Epub 2012 Mar 9. PubMed PMID: 22406239.

11: Lundahl J, Deacon S, Maurice D, Staner L. EEG spectral power density profiles during NREM sleep for gaboxadol and zolpidem in patients with primary insomnia. J Psychopharmacol. 2012 Aug;26(8):1081-7. doi: 10.1177/0269881111424457. Epub 2011 Nov 5. PubMed PMID: 22057018.

12: Kasper S, Ebert B, Larsen K, Tonnoir B. Combining escitalopram with gaboxadol provides no additional benefit in the treatment of patients with severe major depressive disorder. Int J Neuropsychopharmacol. 2012 Jul;15(6):715-25. doi: 10.1017/S146114571100112X. Epub 2011 Oct 19. PubMed PMID: 22008735.

13: Ma J, Dijk DJ, Svetnik V, Tymofyeyev Y, Ray S, Walsh JK, Deacon S. EEG power spectra response to a 4-h phase advance and gaboxadol treatment in 822 men and women. J Clin Sleep Med. 2011 Oct 15;7(5):493-501A. doi: 10.5664/JCSM.1316. PubMed PMID: 22003345; PubMed Central PMCID: PMC3190849.

14: Dijk DJ, Stanley N, Lundahl J, Groeger JA, Legters A, Trap Huusom AK, Deacon S. Enhanced slow wave sleep and improved sleep maintenance after gaboxadol administration during seven nights of exposure to a traffic noise model of transient insomnia. J Psychopharmacol. 2012 Aug;26(8):1096-107. doi: 10.1177/0269881111421971. Epub 2011 Oct 13. PubMed PMID: 22002961.

15: Meera P, Wallner M, Otis TS. Molecular basis for the high THIP/gaboxadol sensitivity of extrasynaptic GABA(A) receptors. J Neurophysiol. 2011 Oct;106(4):2057-64. doi: 10.1152/jn.00450.2011. Epub 2011 Jul 27. PubMed PMID: 21795619; PubMed Central PMCID: PMC3191842.

16: Ramaker MJ, Ford MM, Fretwell AM, Finn DA. Alteration of ethanol drinking in mice via modulation of the GABA(A) receptor with ganaxolone, finasteride, and gaboxadol. Alcohol Clin Exp Res. 2011 Nov;35(11):1994-2007. doi: 10.1111/j.1530-0277.2011.01551.x. Epub 2011 Jun 7. PubMed PMID: 21649668; PubMed Central PMCID: PMC3173599.

17: Kueh SL, Dempster J, Head SI, Morley JW. Reduced postsynaptic GABAA receptor number and enhanced gaboxadol induced change in holding currents in Purkinje cells of the dystrophin-deficient mdx mouse. Neurobiol Dis. 2011 Sep;43(3):558-64. doi: 10.1016/j.nbd.2011.05.002. Epub 2011 May 13. PubMed PMID: 21601636.

18: Madsen KK, Ebert B, Clausen RP, Krogsgaard-Larsen P, Schousboe A, White HS. Selective GABA transporter inhibitors tiagabine and EF1502 exhibit mechanistic differences in their ability to modulate the ataxia and anticonvulsant action of the extrasynaptic GABA(A) receptor agonist gaboxadol. J Pharmacol Exp Ther. 2011 Jul;338(1):214-9. doi: 10.1124/jpet.111.179671. Epub 2011 Mar 30. PubMed PMID: 21450931; PubMed Central PMCID: PMC3126646.

19: Frølund S, Rapin N, Nielsen CU. Gaboxadol has affinity for the proton-coupled amino acid transporter 1, SLC36A1 (hPAT1)--A modelling approach to determine IC(50) values of the three ionic species of gaboxadol. Eur J Pharm Sci. 2011 Feb 14;42(3):192-8. doi: 10.1016/j.ejps.2010.11.009. Epub 2010 Nov 26. PubMed PMID: 21112392.

20: Svetnik V, Ferri R, Ray S, Ma J, Walsh JK, Snyder E, Ebert B, Deacon S. Alterations in cyclic alternating pattern associated with phase advanced sleep are differentially modulated by gaboxadol and zolpidem. Sleep. 2010 Nov;33(11):1562-70. PubMed PMID: 21102998; PubMed Central PMCID: PMC2954706.