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Identification
NameTenocyclidine
Accession NumberDB01520
TypeSmall Molecule
GroupsExperimental, Illicit
DescriptionTenocyclidine (TCP, thienyl cyclohexylpiperidine) is a dissociative anesthetic drug with stimulant and hallucinogenic effects. It is similar in effects to phencyclidine but is considerably more potent. Due to its similarity in effects to PCP, TCP was placed into the Schedule I list of illegal drugs in the 1970s, although it was only briefly abused in the 1970s and 1980s and is now little known. [Wikipedia]
Structure
Thumb
Synonyms
TCP
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII8BQ45Q6VCL
CAS number21500-98-1
WeightAverage: 249.415
Monoisotopic: 249.155120431
Chemical FormulaC15H23NS
InChI KeyJUZZEWSCNBCFRL-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
Pharmacology
IndicationBecause 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.
Structured Indications Not Available
PharmacodynamicsTenocyclidine (TCP) has slightly different binding properties to phencyclidine (PCP), with more affinity for NMDA receptors but less affinity for sigma receptors.
Mechanism of actionThe 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).
TargetKindPharmacological actionActionsOrganismUniProt ID
Glutamate receptor ionotropic, NMDA 3AProteinyes
antagonist
HumanQ8TCU5 details
Glutamate receptor ionotropic, NMDA 3BProteinyes
antagonist
HumanO60391 details
Glutamate receptor ionotropic, NMDA 2AProteinyes
antagonist
HumanQ12879 details
Glutamate receptor ionotropic, NMDA 2CProteinyes
antagonist
HumanQ14957 details
Glutamate receptor ionotropic, NMDA 2BProteinyes
antagonist
HumanQ13224 details
Glutamate receptor ionotropic, NMDA 2DProteinunknown
antagonist
HumanO15399 details
Alpha-7 nicotinic cholinergic receptor subunitProteinunknown
antagonist
HumanQ693P7 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0313 mg/mLALOGPS
logP5.04ALOGPS
logP4.4ChemAxon
logS-3.9ALOGPS
pKa (Strongest Basic)10.44ChemAxon
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 RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassAmines
Sub ClassAralkylamines
Direct ParentAralkylamines
Alternative Parents
Substituents
  • Aralkylamine
  • Cyclohexylamine
  • Piperidine
  • Heteroaromatic compound
  • Thiophene
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
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 play a role in the development of dendritic spines. May play a role in PPP2CB-NMDAR mediated signaling mechanism (By similarity).
Gene Name:
GRIN3A
Uniprot ID:
Q8TCU5
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. [PubMed:2538766 ]
  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. [PubMed:17157509 ]
Kind
Protein
Organism
Human
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
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. [PubMed:2538766 ]
  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. [PubMed:17157509 ]
Kind
Protein
Organism
Human
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 subunits.
Gene Name:
GRIN2A
Uniprot ID:
Q12879
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. [PubMed:2538766 ]
  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. [PubMed:17157509 ]
Kind
Protein
Organism
Human
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
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. [PubMed:2538766 ]
Kind
Protein
Organism
Human
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 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 ...
Gene Name:
GRIN2B
Uniprot ID:
Q13224
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. [PubMed:2538766 ]
Kind
Protein
Organism
Human
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
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. [PubMed:2538766 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
antagonist
General Function:
Not Available
Specific Function:
Not Available
Gene Name:
CHRNA7
Uniprot ID:
Q693P7
Molecular Weight:
2987.635 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. [PubMed:11551210 ]
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Drug created on July 31, 2007 07:10 / Updated on August 17, 2016 12:23