Tenocyclidine
Explore a selection of our essential drug information below, or:
Overview
- DrugBank ID
- DB01520
- Type
- Small Molecule
- Clinical Trials
- Phase 0
- 0
- Phase 1
- 0
- Phase 2
- 0
- Phase 3
- 0
- Phase 4
- 0
- Mechanism of Action
- Glutamate receptor ionotropic, NMDA 3AAntagonist
- Glutamate receptor ionotropic, NMDA 3BAntagonist
- Glutamate receptor ionotropic, NMDA 2AAntagonist
- + 2 more targets
- Glutamate receptor ionotropic, NMDA 3A
Identification
- Generic Name
- Tenocyclidine
- DrugBank Accession Number
- DB01520
- Background
Tenocyclidine (TCP, thienyl cyclohexylpiperidine) is a dissociative anesthetic drug with stimulant and hallucinogenic effects. It is more potent than phencyclidine and hence, this drug was classified under the schedule 1 in 1970.
- Type
- Small Molecule
- Groups
- Experimental, Illicit, Investigational
- Structure
- Weight
- Average: 249.415
Monoisotopic: 249.155120431 - Chemical Formula
- C15H23NS
- Synonyms
- 1-[1-(thiophen-2-yl)cyclohexyl]piperidine
- TCP
- Tenociclidina
- Tenocyclidine
- Tenocyclidinum
- Thienyl cyclohexylpiperidine
Pharmacology
- Indication
Because of its high affinity for the phencyclidine binding site on the NMDA receptor, the 3H radiolabelled form of tenocyclidine is widely used in research into NMDA receptors.
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- Pharmacodynamics
When compared to phencyclidine, tenocyclidine presents more affinity for NMDA receptors and less affinity for sigma receptors.
- Mechanism of action
The primary interactions are as a non-competitive antagonist at the 3A-subunit of the NMDAR in Homo sapiens. TCP is known to bind, with relatively high affinity, to the D1 subunit of the human DAT, in addition to displaying a positive antagonistic effect at the α7-subunit of the Nicotinic Acetylcholine Receptor (nAChR). It also binds to the mu-opioid receptor, which seems to be a central part of the mechanism of action of drugs in this class. (For example, Dizocilpine [MK-801] shows little appreciable analgesic effect despite having a high specificity for the NMDA-3A and NMDA-3B subunits - this may well be mediated by the lack of related efficacy at the mu-opioid receptor, though the NMDAR certainly does play a role in transmission of pain signals).
Target Actions Organism AGlutamate receptor ionotropic, NMDA 3A antagonistHumans AGlutamate receptor ionotropic, NMDA 3B antagonistHumans AGlutamate receptor ionotropic, NMDA 2A antagonistHumans AGlutamate receptor ionotropic, NMDA 2C antagonistHumans AGlutamate receptor ionotropic, NMDA 2B antagonistHumans UNeuronal acetylcholine receptor subunit alpha-7 antagonistHumans UGlutamate receptor ionotropic, NMDA 2D antagonistHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareMemantine The risk or severity of adverse effects can be increased when Tenocyclidine is combined with Memantine. - Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Tenocyclidine hydrochloride 425WW340S2 1867-65-8 IIPLEZRBGQCZMF-UHFFFAOYSA-N
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
- Kingdom
- Organic compounds
- Super Class
- Organic nitrogen compounds
- Class
- Organonitrogen compounds
- Sub Class
- Amines
- Direct Parent
- Aralkylamines
- Alternative Parents
- Cyclohexylamines / Piperidines / Thiophenes / Heteroaromatic compounds / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Cyclohexylamine / Heteroaromatic compound / Hydrocarbon derivative / Organoheterocyclic compound / Organopnictogen compound / Piperidine / Tertiary aliphatic amine
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- piperidines, tertiary amino compound, thiophenes (CHEBI:64610)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 8BQ45Q6VCL
- CAS number
- 21500-98-1
- InChI Key
- JUZZEWSCNBCFRL-UHFFFAOYSA-N
- InChI
- InChI=1S/C15H23NS/c1-3-9-15(10-4-1,14-8-7-13-17-14)16-11-5-2-6-12-16/h7-8,13H,1-6,9-12H2
- IUPAC Name
- 1-[1-(thiophen-2-yl)cyclohexyl]piperidine
- SMILES
- C1CCN(CC1)C1(CCCCC1)C1=CC=CS1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 62751
- PubChem Substance
- 46505124
- ChemSpider
- 56495
- BindingDB
- 50004107
- ChEBI
- 64610
- ChEMBL
- CHEMBL279676
- ZINC
- ZINC000000002131
- Wikipedia
- Tenocyclidine
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0313 mg/mL ALOGPS logP 5.04 ALOGPS logP 4.4 Chemaxon logS -3.9 ALOGPS pKa (Strongest Basic) 10.15 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 3.24 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 74.54 m3·mol-1 Chemaxon Polarizability 29.28 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9928 Blood Brain Barrier + 0.9938 Caco-2 permeable + 0.7111 P-glycoprotein substrate Substrate 0.5415 P-glycoprotein inhibitor I Non-inhibitor 0.6979 P-glycoprotein inhibitor II Non-inhibitor 0.6053 Renal organic cation transporter Inhibitor 0.7012 CYP450 2C9 substrate Non-substrate 0.779 CYP450 2D6 substrate Non-substrate 0.7953 CYP450 3A4 substrate Non-substrate 0.5754 CYP450 1A2 substrate Non-inhibitor 0.7973 CYP450 2C9 inhibitor Non-inhibitor 0.8693 CYP450 2D6 inhibitor Inhibitor 0.8978 CYP450 2C19 inhibitor Non-inhibitor 0.7375 CYP450 3A4 inhibitor Non-inhibitor 0.8308 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.9405 Ames test Non AMES toxic 0.7056 Carcinogenicity Non-carcinogens 0.9387 Biodegradation Not ready biodegradable 0.9905 Rat acute toxicity 3.1153 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.906 hERG inhibition (predictor II) Inhibitor 0.5873
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0udi-0190000000-3c1b49ca2779d931c2b6 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-0090000000-b56cf7f9a3cfe10a389a Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0gb9-0940000000-91b9158827df30506ac0 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-0090000000-b8317ef49a30fe0e013e Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00lr-8910000000-9af8896f2dfc4f022b8e Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-01q9-9410000000-15a8b1cbeb8b493adfd9 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 158.9280588 predictedDarkChem Lite v0.1.0 [M-H]- 158.45038 predictedDeepCCS 1.0 (2019) [M+H]+ 159.1683588 predictedDarkChem Lite v0.1.0 [M+H]+ 160.80838 predictedDeepCCS 1.0 (2019) [M+Na]+ 159.2071588 predictedDarkChem Lite v0.1.0 [M+Na]+ 167.80373 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- NMDA receptor subtype of glutamate-gated ion channels with reduced single-channel conductance, low calcium permeability and low voltage-dependent sensitivity to magnesium. Mediated by glycine. During the development of neural circuits, plays a role in the synaptic refinement period, restricting spine maturation and growth. By competing with GIT1 interaction with ARHGEF7/beta-PIX, may reduce GIT1/ARHGEF7-regulated local activation of RAC1, hence affecting signaling and limiting the maturation and growth of inactive synapses. May also play a role in PPP2CB-NMDAR mediated signaling mechanism
- Specific Function
- calcium channel activity
- Gene Name
- GRIN3A
- Uniprot ID
- Q8TCU5
- Uniprot Name
- Glutamate receptor ionotropic, NMDA 3A
- Molecular Weight
- 125464.07 Da
References
- Stirling JM, Cross AJ, Green AR: The binding of [3H]thienyl cyclohexylpiperidine ([3H]TCP) to the NMDA-phencyclidine receptor complex. Neuropharmacology. 1989 Jan;28(1):1-7. [Article]
- Geldenhuys WJ, Malan SF, Bloomquist JR, Van der Schyf CJ: Structure-activity relationships of pentacycloundecylamines at the N-methyl-d-aspartate receptor. Bioorg Med Chem. 2007 Feb 1;15(3):1525-32. Epub 2006 Sep 29. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- NMDA receptor subtype of glutamate-gated ion channels with reduced single-channel conductance, low calcium permeability and low voltage-dependent sensitivity to magnesium. Mediated by glycine
- Specific Function
- calcium channel activity
- Gene Name
- GRIN3B
- Uniprot ID
- O60391
- Uniprot Name
- Glutamate receptor ionotropic, NMDA 3B
- Molecular Weight
- 112990.98 Da
References
- Stirling JM, Cross AJ, Green AR: The binding of [3H]thienyl cyclohexylpiperidine ([3H]TCP) to the NMDA-phencyclidine receptor complex. Neuropharmacology. 1989 Jan;28(1):1-7. [Article]
- Geldenhuys WJ, Malan SF, Bloomquist JR, Van der Schyf CJ: Structure-activity relationships of pentacycloundecylamines at the N-methyl-d-aspartate receptor. Bioorg Med Chem. 2007 Feb 1;15(3):1525-32. Epub 2006 Sep 29. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Component of NMDA receptor complexes that function as heterotetrameric, ligand-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Channel activation requires binding of the neurotransmitter glutamate to the epsilon subunit, glycine binding to the zeta subunit, plus membrane depolarization to eliminate channel inhibition by Mg(2+) (PubMed:8768735, PubMed:26919761, PubMed:26875626, PubMed:28105280). Sensitivity to glutamate and channel kinetics depend on the subunit composition; channels containing GRIN1 and GRIN2A have lower sensitivity to glutamate and faster deactivation kinetics than channels formed by GRIN1 and GRIN2B (PubMed:26919761, PubMed:26875626). Contributes to the slow phase of excitatory postsynaptic current, long-term synaptic potentiation, and learning (By similarity). Participates in the synaptic plasticity regulation through activation by the L-glutamate releaseed by BEST1, into the synaptic cleft, upon F2R/PAR-1 activation in astrocyte (By similarity)
- Specific Function
- amyloid-beta binding
- Gene Name
- GRIN2A
- Uniprot ID
- Q12879
- Uniprot Name
- Glutamate receptor ionotropic, NMDA 2A
- Molecular Weight
- 165281.215 Da
References
- Stirling JM, Cross AJ, Green AR: The binding of [3H]thienyl cyclohexylpiperidine ([3H]TCP) to the NMDA-phencyclidine receptor complex. Neuropharmacology. 1989 Jan;28(1):1-7. [Article]
- Geldenhuys WJ, Malan SF, Bloomquist JR, Van der Schyf CJ: Structure-activity relationships of pentacycloundecylamines at the N-methyl-d-aspartate receptor. Bioorg Med Chem. 2007 Feb 1;15(3):1525-32. Epub 2006 Sep 29. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Component of NMDA receptor complexes that function as heterotetrameric, ligand-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Channel activation requires binding of the neurotransmitter glutamate to the epsilon subunit, glycine binding to the zeta subunit, plus membrane depolarization to eliminate channel inhibition by Mg(2+) (PubMed:26875626). Sensitivity to glutamate and channel kinetics depend on the subunit composition (Probable). Plays a role in regulating the balance between excitatory and inhibitory activity of pyramidal neurons in the prefrontal cortex. Contributes to the slow phase of excitatory postsynaptic current, long-term synaptic potentiation, and learning (By similarity)
- Specific Function
- glutamate-gated calcium ion channel activity
- Gene Name
- GRIN2C
- Uniprot ID
- Q14957
- Uniprot Name
- Glutamate receptor ionotropic, NMDA 2C
- Molecular Weight
- 134207.77 Da
References
- Stirling JM, Cross AJ, Green AR: The binding of [3H]thienyl cyclohexylpiperidine ([3H]TCP) to the NMDA-phencyclidine receptor complex. Neuropharmacology. 1989 Jan;28(1):1-7. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Component of NMDA receptor complexes that function as heterotetrameric, ligand-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Channel activation requires binding of the neurotransmitter glutamate to the epsilon subunit, glycine binding to the zeta subunit, plus membrane depolarization to eliminate channel inhibition by Mg(2+) (PubMed:26875626, PubMed:26919761, PubMed:28126851, PubMed:8768735). Sensitivity to glutamate and channel kinetics depend on the subunit composition (PubMed:26875626, PubMed:8768735). In concert with DAPK1 at extrasynaptic sites, acts as a central mediator for stroke damage. Its phosphorylation at Ser-1303 by DAPK1 enhances synaptic NMDA receptor channel activity inducing injurious Ca2+ influx through them, resulting in an irreversible neuronal death. Contributes to neural pattern formation in the developing brain. Plays a role in long-term depression (LTD) of hippocampus membrane currents and in synaptic plasticity (By similarity)
- Specific Function
- amyloid-beta binding
- Gene Name
- GRIN2B
- Uniprot ID
- Q13224
- Uniprot Name
- Glutamate receptor ionotropic, NMDA 2B
- Molecular Weight
- 166365.885 Da
References
- Stirling JM, Cross AJ, Green AR: The binding of [3H]thienyl cyclohexylpiperidine ([3H]TCP) to the NMDA-phencyclidine receptor complex. Neuropharmacology. 1989 Jan;28(1):1-7. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The channel is blocked by alpha-bungarotoxin
- Specific Function
- acetylcholine binding
- Gene Name
- CHRNA7
- Uniprot ID
- P36544
- Uniprot Name
- Neuronal acetylcholine receptor subunit alpha-7
- Molecular Weight
- 56448.925 Da
References
- Pagan OR, Eterovic VA, Garcia M, Vergne D, Basilio CM, Rodriguez AD, Hann RM: Cembranoid and long-chain alkanol sites on the nicotinic acetylcholine receptor and their allosteric interaction. Biochemistry. 2001 Sep 18;40(37):11121-30. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Component of NMDA receptor complexes that function as heterotetrameric, ligand-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Channel activation requires binding of the neurotransmitter glutamate to the epsilon subunit, glycine binding to the zeta subunit, plus membrane depolarization to eliminate channel inhibition by Mg(2+) (PubMed:26875626, PubMed:27616483, PubMed:28126851, PubMed:9489750). Sensitivity to glutamate and channel kinetics depend on the subunit composition (PubMed:9489750)
- Specific Function
- glutamate binding
- Gene Name
- GRIN2D
- Uniprot ID
- O15399
- Uniprot Name
- Glutamate receptor ionotropic, NMDA 2D
- Molecular Weight
- 143750.685 Da
References
- Stirling JM, Cross AJ, Green AR: The binding of [3H]thienyl cyclohexylpiperidine ([3H]TCP) to the NMDA-phencyclidine receptor complex. Neuropharmacology. 1989 Jan;28(1):1-7. [Article]
Drug created at July 31, 2007 13:10 / Updated at February 13, 2024 02:57