Page last updated: 2024-12-06

tenocyclidine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

tenocyclidine : A tertiary amino compound that consists of cyclohexane having piperidin-1-yl and thiophen-2-yl groups attached at position 1. A dissociative anaesthetic drug with halluccinogenic and stimulant effects. Its effects are similar to those of phencyclidine (PCP, an analogue with the thienyl group replaced by phenyl), but it is rather more potent. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID62751
CHEMBL ID279676
CHEBI ID64610
SCHEMBL ID517558
MeSH IDM0058785

Synonyms (43)

Synonym
1-(1-(2-thienyl)cyclohexyl)piperidine
tenocyclidinum [inn-latin]
tenocyclidine [inn]
tenociclidina [inn-spanish]
brn 1246605
((thienyl-2)-1 cyclohexyle)-n piperidine [french]
piperidine, 1-(1-(2-thienyl)cyclohexyl)-
dea no. 7470
tenocyclidine
DB01520
NCGC00160467-01
thienyl cyclohexylpiperidine
1-[1-(thiophen-2-yl)cyclohexyl]piperidine
thienylcyclidine
CHEMBL279676 ,
thienylphencyclidine
chebi:64610 ,
1-(1-thiophen-2-ylcyclohexyl)piperidine
AKOS005066628
bdbm50004107
1-(1-thiophen-2-yl-cyclohexyl)-piperidine
1-(1-[2-thienyl]cyclohexyl)piperidine
dtxcid1026168
cas-21500-98-1
dtxsid3046168 ,
tox21_111833
unii-8bq45q6vcl
((thienyl-2)-1 cyclohexyle)-n piperidine
tenocyclidinum
hsdb 7637
8bq45q6vcl ,
21500-98-1
tenociclidina
5-20-03-00347 (beilstein handbook reference)
1-[1-(2-thienyl)cyclohexyl]piperidine
SCHEMBL517558
gk-0
n-(1-(2-thienyl)cyclohexyl)piperidine
tenocyclidine [hsdb]
((thienyl-2)-1 cyclohexyl)-n piperidine
1-[1(2-thienyl)cyclohexyl]piperidine (tenocyclidine)
n[1-(2-thienyl)cyclohexyl]piperidine
Q2907272

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"The capacity of thienylcyclohexylpiperidine (TCP), a non-competitive blocker of the N-methyl-D-aspartate (NMDA) receptor, to counteract the convulsant, lethal, and neuropathological effects of 2 x LD50 of soman (an irreversible inhibitor of cholinesterase) was investigated in guinea-pigs treated by pyridostigmine and atropine sulphate."( Effects of thienylphencyclidine (TCP) on seizure activity and brain damage produced by soman in guinea-pigs: ECoG correlates of neurotoxicity.
Carpentier, P; de Groot, DM; Foquin, A; Kamenka, JM; Lallement, G; Lerner-Natoli, M; Rondouin, G, 2001
)
0.31

Pharmacokinetics

ExcerptReferenceRelevance
" For the pharmacokinetic studies, [3H]TCP and 1 mg/kg unlabeled TCP were administered as an iv bolus dose."( The pharmacokinetics of [3H]1-[1-(2-thienyl)cyclohexyl]piperidine (TCP) in Sprague-Dawley rats.
Bui, H; Owens, SM; Plunkett, LM; Zorbas, M,
)
0.13

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51

Dosage Studied

ExcerptRelevanceReference
" The dose-response curves for induction of behavior was very different from that for increasing the concentration of i beta-E in plasma."( Phencyclidine increased release of beta-endorphin from anterior lobe of the pituitary.
Contreras, PC; Farah, JM; Jacobson, AE; Rice, KC, 1991
)
0.28
" These results were confirmed by studies employing a self- and cross-displacement design and dose-response surfaces for SKF and TCP, with and without blockade by haloperidol of the sigma site."( Quantitative characterization of multiple binding sites for phencyclidine and N-allylnormetazocine in membranes from rat and guinea pig brain.
Katki, AG; Munson, PJ; Rodbard, D; Schwarz, S; Zhou, GZ, 1991
)
0.28
" Addition of GTP resulted in a rightward shift in the glutamate dose-response curve and a decrease in the maximum level of stimulation."( Guanine nucleotide modulation of [3H]TCP binding to the NMDA receptor complex.
Compton, RP; Hood, WF; Monahan, JB; Thomas, JW, 1990
)
0.28
" As in the in vitro experiments, the dose-response curve for the antagonist was shifted rightward in a parallel fashion when D-serine was coinjected."( Activity of 5,7-dichlorokynurenic acid, a potent antagonist at the N-methyl-D-aspartate receptor-associated glycine binding site.
Baron, BM; Harrison, BL; McDonald, IA; Miller, FP; Palfreyman, MG; Salituro, FG; Schmidt, CJ; Sorensen, SM; White, HS, 1990
)
0.28
" Moreover, the stimulation of [3H]TCP binding induced by D-cycloserine in the presence of various fixed concentrations of glycine results in a family of dose-response curves which asymptotically converge to 40-50% of the maximal stimulation induced by glycine alone."( D-cycloserine: a ligand for the N-methyl-D-aspartate coupled glycine receptor has partial agonist characteristics.
Compton, RP; Hood, WF; Monahan, JB, 1989
)
0.28
" We found that excitatory amino acid agonists evoked somatostatin release in the following order of potency: quisqualate greater than glutamate = N-methyl-D-aspartate (NMDA) greater than kainate, as calculated from the dose-response curves."( Glutamate stimulates somatostatin release from diencephalic neurons in primary culture.
Astier, H; Tapia-Arancibia, L, 1988
)
0.27
" Generally, an orderly inverted U-shaped dose-response curve for rates of self-injection has been observed."( Animal models of intravenous phencyclinoid self-administration.
Marquis, KL; Moreton, JE, 1987
)
0.27
" Dose-response curves and median effective doses were determined for phencyclidine, N-ethyl-1-phenylcyclohexylamine, 1-(1-(2-thienyl) cyclohexyl) piperidine and ketamine."( Comparison of phencyclidine and three analogues on fixed-interval performance in rhesus monkeys.
Balster, RL; Brady, KT; Meltzer, LT; Schwertz, D, 1980
)
0.26
"5, 1, and 2 mg/kg for TCP, the second dosage corresponding to the minimal required for antiseizure activity."( Effects of TCP on spatial memory: comparison with MK-801.
Blanchet, G; Filliat, P,
)
0.13
" Consequently, the major goal of these studies was to determine whether a monoclonal antibody Fab fragment (of IgG) could be used as an effective drug class-selective antagonist and to understand better the dose-response relationships for reversing CNS drug toxicity."( Pharmacodynamics of a monoclonal antiphencyclidine Fab with broad selectivity for phencyclidine-like drugs.
Hardin, JS; Owens, SM; Proksch, JW; Wessinger, WD, 1998
)
0.3
" In an attempt to further clarify the mechanisms underlying these degeneration patterns, autoradiographic studies using a variety of receptor ligands were conducted in animals 21 days after an identical dosage of the continuous phencyclidine administration employed in the previous degeneration studies."( Long-term changes in brain following continuous phencyclidine administration: an autoradiographic study using flunitrazepam, ketanserin, mazindol, quinuclidinyl benzilate, piperidyl-3,4-3H(N)-TCP, and AMPA receptor ligands.
Ellison, G; Keys, A; Noguchi, K, 1999
)
0.3
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (4)

RoleDescription
central nervous system stimulantAny drug that enhances the activity of the central nervous system.
neuroprotective agentAny compound that can be used for the treatment of neurodegenerative disorders.
hallucinogenDrugs capable of inducing illusions, hallucinations, delusions, paranoid ideations and other alterations of mood and thinking.
NMDA receptor antagonistAny substance that inhibits the action of N-methyl-D-aspartate (NMDA) receptors. They tend to induce a state known as dissociative anesthesia, marked by catalepsy, amnesia, and analgesia, while side effects can include hallucinations, nightmares, and confusion. Due to their psychotomimetic effects, many NMDA receptor antagonists are used as recreational drugs.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (3)

ClassDescription
piperidines
tertiary amino compoundA compound formally derived from ammonia by replacing three hydrogen atoms by organyl groups.
thiophenesCompounds containing at least one thiophene ring.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (3)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
pregnane X nuclear receptorHomo sapiens (human)Potency15.84890.005428.02631,258.9301AID1346985
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Lysosomal Pro-X carboxypeptidaseHomo sapiens (human)IC50 (µMol)0.02000.00530.60331.9000AID157589
Sigma non-opioid intracellular receptor 1Rattus norvegicus (Norway rat)IC50 (µMol)0.24000.00030.55704.2000AID204608
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (9)

Processvia Protein(s)Taxonomy
regulation of thyroid hormone mediated signaling pathwayLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
plasma kallikrein-kinin cascadeLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
proteolysisLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
glucose homeostasisLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
energy homeostasisLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
regulation of reactive oxygen species metabolic processLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
angiogenesis involved in wound healingLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
negative regulation of systemic arterial blood pressureLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
regulation of blood vessel endothelial cell migrationLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (3)

Processvia Protein(s)Taxonomy
serine-type carboxypeptidase activityLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
protein bindingLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
dipeptidyl-peptidase activityLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
plasma membraneLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
azurophil granule membraneLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
intracellular membrane-bounded organelleLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
basal part of cellLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
extracellular exosomeLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
ficolin-1-rich granule membraneLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (9)

Assay IDTitleYearJournalArticle
AID504749qHTS profiling for inhibitors of Plasmodium falciparum proliferation2011Science (New York, N.Y.), Aug-05, Volume: 333, Issue:6043
Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets.
AID204608Inhibition of [3H]- N-allylnormetazocine ([3H]NANM) binding to sigma receptor1989Journal of medicinal chemistry, Jun, Volume: 32, Issue:6
Phencyclidine-like effects of tetrahydroisoquinolines and related compounds.
AID229187Inhibition of specific binding of [125I]PIPAG to sigma receptor in Guinea pig brain membranes1992Journal of medicinal chemistry, Dec-11, Volume: 35, Issue:25
Radiosynthesis, cerebral distribution, and binding of [125I]-1-(p-iodophenyl)-3-(1-adamantyl)guanidine, a ligand for sigma binding sites.
AID157589Inhibition of [3H]1-[1-(2-thienyl) piperidine ([3H]TCP) binding to phencyclidine receptor1989Journal of medicinal chemistry, Jun, Volume: 32, Issue:6
Phencyclidine-like effects of tetrahydroisoquinolines and related compounds.
AID229193Inhibition of specific binding of [3H]NANM of sigma receptor in Guinea pig brain membranes1992Journal of medicinal chemistry, Dec-11, Volume: 35, Issue:25
Radiosynthesis, cerebral distribution, and binding of [125I]-1-(p-iodophenyl)-3-(1-adamantyl)guanidine, a ligand for sigma binding sites.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID493017Wombat Data for BeliefDocking1992Journal of medicinal chemistry, Dec-11, Volume: 35, Issue:25
Radiosynthesis, cerebral distribution, and binding of [125I]-1-(p-iodophenyl)-3-(1-adamantyl)guanidine, a ligand for sigma binding sites.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (258)

TimeframeStudies, This Drug (%)All Drugs %
pre-199077 (29.84)18.7374
1990's156 (60.47)18.2507
2000's20 (7.75)29.6817
2010's4 (1.55)24.3611
2020's1 (0.39)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 24.52

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index24.52 (24.57)
Research Supply Index5.58 (2.92)
Research Growth Index4.31 (4.65)
Search Engine Demand Index31.58 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (24.52)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (0.38%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other264 (99.62%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]