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
Structure for Tenocyclidine (DB01520)
- 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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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 UAlpha-7 nicotinic cholinergic receptor subunit 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
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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. 
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- Not Available
Products
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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
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 Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Protein phosphatase 2a binding
- Specific 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. May ...
- 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 glutamate receptor activity
- Specific 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.
- 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
- Zinc ion binding
- Specific Function
- NMDA receptor subtype of glutamate-gated ion channels possesses high calcium permeability and voltage-dependent sensitivity to magnesium. Activation requires binding of agonist to both types of sub...
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Nmda glutamate receptor activity
- Specific Function
- NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine.
- 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
- Zinc ion binding
- Specific Function
- NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine. In concert with DAPK1 at extrasynaptic site...
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Not Available
- Specific Function
- Not Available
- Gene Name
- CHRNA7
- Uniprot ID
- Q693P7
- Uniprot Name
- Alpha-7 nicotinic cholinergic receptor subunit
- Molecular Weight
- 2987.635 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
- Nmda glutamate receptor activity
- Specific Function
- NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine.
- 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 21, 2021 18:51