TCTHP

TCTHP
Identifiers
  • 1,2,3,6-tetrahydro-1-[1-(2-thienyl)cyclohexyl]pyridine
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H21NS
Molar mass247.40 g·mol−1
3D model (JSmol)
  • C1CCC(CC1)(C2=CC=CS2)N3CCC=CC3
  • InChI=1S/C15H21NS/c1-3-9-15(10-4-1,14-8-7-13-17-14)16-11-5-2-6-12-16/h2,5,7-8,13H,1,3-4,6,9-12H2
  • Key:NDTNWLZCHFUWIS-UHFFFAOYSA-N

TCTHP is a designer drug from the arylcyclohexylamine family, which has dissociative-like effects in animal studies. It is an analogue of tenocyclidine where the piperidine ring has been replaced by an unsaturated 1,2,3,6-tetrahydropyridine ring. Similarly to tenocyclidine itself and other related compounds such as ketamine and phencyclidine, TCTHP acts as an NMDA antagonist. While NMDA antagonists can be neurotoxic at high doses, they can also be neuroprotective under certain conditions, particularly in preventing death of brain tissue following conditions of transient hypoxia such as those which may occur when the supply of oxygenated blood to the brain is cut off following medical events such as stroke or heart attack. TCTHP and related compounds were developed in an attempt to exploit this property and develop potential medications for the alleviation of brain injury following transient hypoxic events, and show neuroprotective effects against hypoxic brain injury in animal models.[1][2]

References

  1. ^ Thurkauf A, de Costa B, Mattson MV, France CP, Price MT, Olney JW, et al. (August 1990). "Synthesis, phencyclidine-like pharmacology, and antiischemic potential of meta-substituted 1-(1-phenylcyclohexyl)-1,2,3,6-tetrahydropyridines". Journal of Medicinal Chemistry. 33 (8): 2211–2215. doi:10.1021/jm00170a027. PMID 2374147.
  2. ^ US 5604255, Rice KC, Jacobson AE, Thurkauf A, Mattson MV, O'Donohue TL, Contreras PC, Gray NM, "N-(1-thienylcycloalkyl)alkenylamines for treatment of neurotoxic injury.", issued 18 February 1997, assigned to GD Searle LLC and US Department of Health and Human Services 
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