Tenocyclidine

Overview

DrugBank ID
DB01520
Type
Small Molecule
US Approved
NO
Other Approved
NO

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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Contraindications & Blackbox Warnings
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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).

TargetActionsOrganism
AGlutamate receptor ionotropic, NMDA 3A
antagonist
Humans
AGlutamate receptor ionotropic, NMDA 3B
antagonist
Humans
AGlutamate receptor ionotropic, NMDA 2A
antagonist
Humans
AGlutamate receptor ionotropic, NMDA 2C
antagonist
Humans
AGlutamate receptor ionotropic, NMDA 2B
antagonist
Humans
UNeuronal acetylcholine receptor subunit alpha-7
antagonist
Humans
UGlutamate receptor ionotropic, NMDA 2D
antagonist
Humans
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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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.
DrugInteraction
MemantineThe risk or severity of adverse effects can be increased when Tenocyclidine is combined with Memantine.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Tenocyclidine hydrochloride425WW340S21867-65-8IIPLEZRBGQCZMF-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
PubChem Compound
62751
PubChem Substance
46505124
ChemSpider
56495
BindingDB
50004107
ChEBI
64610
ChEMBL
CHEMBL279676
ZINC
ZINC000000002131
Wikipedia
Tenocyclidine

Clinical Trials

Clinical Trials
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PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns

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
PropertyValueSource
Water Solubility0.0313 mg/mLALOGPS
logP5.04ALOGPS
logP4.4Chemaxon
logS-3.9ALOGPS
pKa (Strongest Basic)10.15Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count1Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area3.24 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity74.54 m3·mol-1Chemaxon
Polarizability29.28 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9928
Blood Brain Barrier+0.9938
Caco-2 permeable+0.7111
P-glycoprotein substrateSubstrate0.5415
P-glycoprotein inhibitor INon-inhibitor0.6979
P-glycoprotein inhibitor IINon-inhibitor0.6053
Renal organic cation transporterInhibitor0.7012
CYP450 2C9 substrateNon-substrate0.779
CYP450 2D6 substrateNon-substrate0.7953
CYP450 3A4 substrateNon-substrate0.5754
CYP450 1A2 substrateNon-inhibitor0.7973
CYP450 2C9 inhibitorNon-inhibitor0.8693
CYP450 2D6 inhibitorInhibitor0.8978
CYP450 2C19 inhibitorNon-inhibitor0.7375
CYP450 3A4 inhibitorNon-inhibitor0.8308
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9405
Ames testNon AMES toxic0.7056
CarcinogenicityNon-carcinogens0.9387
BiodegradationNot ready biodegradable0.9905
Rat acute toxicity3.1153 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.906
hERG inhibition (predictor II)Inhibitor0.5873
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0190000000-3c1b49ca2779d931c2b6
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-b56cf7f9a3cfe10a389a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0gb9-0940000000-91b9158827df30506ac0
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-b8317ef49a30fe0e013e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00lr-8910000000-9af8896f2dfc4f022b8e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01q9-9410000000-15a8b1cbeb8b493adfd9
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-158.9280588
predicted
DarkChem Lite v0.1.0
[M-H]-158.45038
predicted
DeepCCS 1.0 (2019)
[M+H]+159.1683588
predicted
DarkChem Lite v0.1.0
[M+H]+160.80838
predicted
DeepCCS 1.0 (2019)
[M+Na]+159.2071588
predicted
DarkChem Lite v0.1.0
[M+Na]+167.80373
predicted
DeepCCS 1.0 (2019)

Targets

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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
  1. 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]
  2. 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
  1. 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]
  2. 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
  1. 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]
  2. 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]
  3. 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
  1. 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
  1. 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]
  2. 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
  1. 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
  1. 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