Gacyclidine

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

MedKoo CAT#: 527609

CAS#: 68134-81-6

Description: Gacyclidine, also known as OTO-311 and GK-11, is a N-methyl-D-aspartate (NMDA) receptor antagonist potentially for the treatment of tinnitus. Local administration of gacyclidine to the cochlea can suppress salicylate-induced tinnitus. Tritiated gacyclidine and its enantiomers bind to NMDA receptors with binding parameters similar to those of other non-competitive NMDA receptor antagonists.


Price and Availability

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Gacyclidine (OTO-311, GK-11) is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 527609
Name: Gacyclidine
CAS#: 68134-81-6
Chemical Formula: C16H25NS
Exact Mass: 263.1708
Molecular Weight: 263.443
Elemental Analysis: C, 72.95; H, 9.57; N, 5.32; S, 12.17


Synonym: Gacyclidine; OTO-311; GK-11; OTO 311; GK 11; OTO311; GK11

IUPAC/Chemical Name: 1-((1S,2S)-2-methyl-1-(thiophen-2-yl)cyclohexyl)piperidine

InChi Key: DKFAAPPUYWQKKF-HOCLYGCPSA-N

InChi Code: InChI=1S/C16H25NS/c1-14-8-3-4-10-16(14,15-9-7-13-18-15)17-11-5-2-6-12-17/h7,9,13-14H,2-6,8,10-12H2,1H3/t14-,16-/m0/s1

SMILES Code: C[C@@H]1[C@](N2CCCCC2)(C3=CC=CS3)CCCC1


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


References

1: Chenoweth JA, Gerona RR, Ford JB, Sutter ME, Rose JS, Albertson TE, Clarke SO, Owen KP. Altered mental status and end organ damage associated with the use of gacyclidine: a case series. J Med Toxicol. 2015 Mar;11(1):115-20. doi: 10.1007/s13181-014-0415-2. PubMed PMID: 25048606; PubMed Central PMCID: PMC4371039.

2: Wenzel GI, Warnecke A, Stöver T, Lenarz T. Effects of extracochlear gacyclidine perfusion on tinnitus in humans: a case series. Eur Arch Otorhinolaryngol. 2010 May;267(5):691-9. doi: 10.1007/s00405-009-1126-1. PubMed PMID: 19847455.

3: Gerber YN, Privat A, Perrin FE. Gacyclidine improves the survival and reduces motor deficits in a mouse model of amyotrophic lateral sclerosis. Front Cell Neurosci. 2013 Dec 27;7:280. doi: 10.3389/fncel.2013.00280. PubMed PMID: 24409117; PubMed Central PMCID: PMC3873512.

4: Hoizey G, Kaltenbach ML, Dukic S, Lamiable D, Millart H, D'Arbigny P, Vistelle R. Pharmacokinetics of gacyclidine enantiomers in plasma and spinal cord after single enantiomer administration in rats. Int J Pharm. 2001 Oct 23;229(1-2):147-53. PubMed PMID: 11604267.

5: Hirbec H, Gaviria M, Vignon J. Gacyclidine: a new neuroprotective agent acting at the N-methyl-D-aspartate receptor. CNS Drug Rev. 2001 Summer;7(2):172-98. Review. PubMed PMID: 11474423.

6: Hoizey G, Kaltenbach ML, Dukic S, Lamiable D, Lallemand A, Millart H, D'Arbigny P, Vistelle R. Distribution of gacyclidine enantiomers after experimental spinal cord injury in rats: possible involvement of an active transport system. J Pharm Sci. 2001 Jan;90(1):70-8. PubMed PMID: 11064380.

7: Lepeintre JF, D'Arbigny P, Mathé JF, Vigué B, Loubert G, Delcour J, Kempf C, Tadié M. Neuroprotective effect of gacyclidine. A multicenter double-blind pilot trial in patients with acute traumatic brain injury. Neurochirurgie. 2004 Jun;50(2-3 Pt 1):83-95. PubMed PMID: 15213636.

8: Hoizey G, Kaltenbach ML, Dukic S, Lamiable D, Lallemand A, D'Arbigny P, Millart H, Vistelle R. Distribution of gacyclidine enantiomers in spinal cord extracellular fluid. Pharm Res. 2000 Feb;17(2):148-53. PubMed PMID: 10751028.

9: Smith JS, Fulop ZL, Levinsohn SA, Darrell RS, Stein DG. Effects of the novel NMDA receptor antagonist gacyclidine on recovery from medial frontal cortex contusion injury in rats. Neural Plast. 2000;7(1-2):73-91. PubMed PMID: 10709216; PubMed Central PMCID: PMC2565364.

10: Feldblum S, Arnaud S, Simon M, Rabin O, D'Arbigny P. Efficacy of a new neuroprotective agent, gacyclidine, in a model of rat spinal cord injury. J Neurotrauma. 2000 Nov;17(11):1079-93. PubMed PMID: 11101210.

11: Hoizey G, Baccard N, Gourdier B, Lamiable D, Millart H, D'Arbigny P, Vistelle R. Modified gas chromatographic-mass spectrometric assay for the determination of gacyclidine enantiomers in human plasma. J Chromatogr B Biomed Sci Appl. 1999 Aug 20;731(2):317-22. PubMed PMID: 10510786.

12: Hirbec H, Kamenka JM, Privat A, Vignon J. Characterization of 'non-N-methyl-D-Aspartate' binding sites for gacyclidine enantiomers in the rat cerebellar and telencephalic structures. J Neurochem. 2001 Apr;77(1):190-201. PubMed PMID: 11279275.

13: Hirbec H, Privat A, Vignon J. Binding properties of [3H]gacyclidine in the rat central nervous system. Eur J Pharmacol. 2000 Feb 4;388(3):235-9. PubMed PMID: 10675731.

14: Lallement G, Clarençon D, Galonnier M, Baubichon D, Burckhart MF, Peoc'h M. Acute soman poisoning in primates neither pretreated nor receiving immediate therapy: value of gacyclidine (GK-11) in delayed medical support. Arch Toxicol. 1999 Mar;73(2):115-22. PubMed PMID: 10350192.

15: Laplanche L, Kamenka JM, Barbanel G. The novel non-competitive N-methyl-D-aspartate antagonist gacyclidine blocks the glutamate-induced release of hydroxyl radicals in the striatum under conditions in which dizocilpine does not. A microdialysis study in rats. Neurosci Lett. 2000 Jul 28;289(1):49-52. PubMed PMID: 10899406.

16: Lallement G, Baubichon D, Clarençon D, Galonnier M, Peoc'h M, Carpentier P. Review of the value of gacyclidine (GK-11) as adjuvant medication to conventional treatments of organophosphate poisoning: primate experiments mimicking various scenarios of military or terrorist attack by soman. Neurotoxicology. 1999 Aug;20(4):675-84. Review. PubMed PMID: 10499365.

17: Gaviria M, Privat A, d'Arbigny P, Kamenka JM, Haton H, Ohanna F. Neuroprotective effects of gacyclidine after experimental photochemical spinal cord lesion in adult rats: dose-window and time-window effects. J Neurotrauma. 2000 Jan;17(1):19-30. PubMed PMID: 10674755.

18: Gaviria M, Privat A, d'Arbigny P, Kamenka J, Haton H, Ohanna F. Neuroprotective effects of a novel NMDA antagonist, Gacyclidine, after experimental contusive spinal cord injury in adult rats. Brain Res. 2000 Aug 25;874(2):200-9. PubMed PMID: 10960605.

19: Hirbec H, Teilhac J, Kamenka J, Privat A, Vignon J. Binding properties of [3H]gacyclidine (cis(pip/me)-1-[1-(2-thienyl)-2-methylcyclohexyl]piperidine) enantiomers in the rat central nervous system. Brain Res. 2000 Mar 24;859(2):177-92. PubMed PMID: 10719063.

20: Hirbec H, Kamenka JM, Privat A, Vignon J. Interaction of gacyclidine enantiomers with 'non-NMDA' binding sites in the rat central nervous system. Brain Res. 2001 Mar 16;894(2):189-92. PubMed PMID: 11251192.