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Identification
NameTenocyclidine
Accession NumberDB01520
Typesmall molecule
Groupsexperimental, illicit
Description

Tenocyclidine (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
SynonymLanguageCode
TCPNot AvailableNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
Categories
CAS number21500-98-1
WeightAverage: 249.415
Monoisotopic: 249.155120431
Chemical FormulaC15H23NS
InChI KeyInChIKey=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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassPiperidines
SubclassNot Available
Direct parentPiperidines
Alternative parentsThiophenes; Tertiary Amines; Polyamines
Substituentsthiophene; tertiary amine; polyamine; amine; organonitrogen compound
Classification descriptionThis compound belongs to the piperidines. These are compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms.
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.
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).
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
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
ADMET
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 substrate Non-inhibitor 0.8693
CYP450 2D6 substrate Inhibitor 0.8978
CYP450 2C19 substrate Non-inhibitor 0.7375
CYP450 3A4 substrate 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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
water solubility3.13e-02 g/lALOGPS
logP5.04ALOGPS
logP4.4ChemAxon
logS-3.9ALOGPS
pKa (strongest basic)10.44ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count1ChemAxon
hydrogen donor count0ChemAxon
polar surface area3.24ChemAxon
rotatable bond count2ChemAxon
refractivity74.54ChemAxon
polarizability29.28ChemAxon
number of rings3ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
PubChem Compound62751
PubChem Substance46505124
ChemSpider56495
BindingDB50004107
WikipediaTenocyclidine
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

1. Glutamate receptor ionotropic, NMDA 3A

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Glutamate receptor ionotropic, NMDA 3A Q8TCU5 Details

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
  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

2. Glutamate receptor ionotropic, NMDA 3B

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Glutamate receptor ionotropic, NMDA 3B O60391 Details

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
  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

3. Glutamate receptor ionotropic, NMDA 2A

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Glutamate receptor ionotropic, NMDA 2A Q12879 Details

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
  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

4. Glutamate receptor ionotropic, NMDA 2C

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Glutamate receptor ionotropic, NMDA 2C Q14957 Details

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

5. Glutamate receptor ionotropic, NMDA 2B

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Glutamate receptor ionotropic, NMDA 2B Q13224 Details

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

6. Glutamate receptor ionotropic, NMDA 2D

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Glutamate receptor ionotropic, NMDA 2D O15399 Details

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

7. Alpha-7 nicotinic cholinergic receptor subunit

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Alpha-7 nicotinic cholinergic receptor subunit Q693P7 Details

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

Comments
Drug created on July 31, 2007 07:10 / Updated on September 16, 2013 17:14