DrugBank: Tenocyclidine (DB01520)

targets (7)

Identification

Name

Tenocyclidine

Accession Number

DB01520

Type

small molecule

Groups

illicit, experimental

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

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

TCP

Salts

Not Available

Brand names

Not Available

Brand mixtures

Not Available

Categories

Neuroprotective Agents
Anesthetics, Dissociative

CAS number

21500-98-1

Weight

Average: 249.415
Monoisotopic: 249.155120431

Chemical Formula

C₁₅H₂₃NS

InChI Key

InChIKey=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

Plain Text

IUPAC Name

1-[1-(thiophen-2-yl)cyclohexyl]piperidine

SMILES

C1CCN(CC1)C1(CCCCC1)C1=CC=CS1

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Not Available

Classes

Not Available

Substructures

Not Available

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.

Pharmacodynamics

Tenocyclidine (TCP) has slightly different binding properties to phencyclidine (PCP), with more affinity for NMDA receptors but 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).

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

Toxicity

Not Available

Affected organisms

Humans and other mammals

Pathways

Not Available

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	3.13e-02 g/l	ALOGPS
logP	5.04	ALOGPS
logP	4.4	ChemAxon
logS	-3.9	ALOGPS
pKa (strongest basic)	10.44	ChemAxon
physiological charge	1	ChemAxon
hydrogen acceptor count	1	ChemAxon
hydrogen donor count	0	ChemAxon
polar surface area	3.24	ChemAxon
rotatable bond count	2	ChemAxon
refractivity	74.54	ChemAxon
polarizability	29.28	ChemAxon

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
PubChem Compound	62751
PubChem Substance	46505124
ChemSpider	56495
BindingDB	50004107
Wikipedia	http://en.wikipedia.org/wiki/Tenocyclidine

ATC Codes

Not Available

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

Not Available

Interactions

Drug Interactions

Not Available

Food Interactions

Not Available

Targets
1. Glutamate [NMDA] receptor subunit 3A Pharmacological action: yes Actions: antagonist 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 Organism class: human UniProt ID: Q8TCU5 Gene: GRIN3A Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report 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. Pubmed 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 [NMDA] receptor subunit 3B Pharmacological action: yes Actions: antagonist 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 Organism class: human UniProt ID: O60391 Gene: GRIN3B Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report 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. Pubmed 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 [NMDA] receptor subunit epsilon-1 Pharmacological action: yes Actions: antagonist NMDA receptor subtype of glutamate-gated ion channels possesses high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine Organism class: human UniProt ID: Q12879 Gene: GRIN2A Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report 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. Pubmed 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 [NMDA] receptor subunit epsilon-3 Pharmacological action: yes Actions: antagonist NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine Organism class: human UniProt ID: Q14957 Gene: GRIN2C Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report 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. Pubmed 5. Glutamate [NMDA] receptor subunit epsilon-2 Pharmacological action: yes Actions: antagonist NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine Organism class: human UniProt ID: Q13224 Gene: GRIN2B Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report 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. Pubmed 6. Glutamate [NMDA] receptor subunit epsilon-4 Pharmacological action: unknown Actions: antagonist NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine Organism class: human UniProt ID: O15399 Gene: GRIN2D Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report 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. Pubmed 7. Alpha-7 nicotinic cholinergic receptor subunit Pharmacological action: unknown Actions: antagonist Organism class: human UniProt ID: Q693P7 Gene: CHRFAM7A Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report 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. Pubmed

Targets

1. Glutamate [NMDA] receptor subunit 3A

Pharmacological action: yes
Actions: antagonist

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

Organism class: human
UniProt ID: Q8TCU5 Link_out

Gene: GRIN3A Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Pubmed
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 [NMDA] receptor subunit 3B

Pharmacological action: yes
Actions: antagonist

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

Organism class: human
UniProt ID: O60391 Link_out

Gene: GRIN3B Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Pubmed
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 [NMDA] receptor subunit epsilon-1

Pharmacological action: yes
Actions: antagonist

NMDA receptor subtype of glutamate-gated ion channels possesses high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine

Organism class: human
UniProt ID: Q12879 Link_out

Gene: GRIN2A Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Pubmed
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 [NMDA] receptor subunit epsilon-3

Pharmacological action: yes
Actions: antagonist

NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine

Organism class: human
UniProt ID: Q14957 Link_out

Gene: GRIN2C Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Pubmed

5. Glutamate [NMDA] receptor subunit epsilon-2

Pharmacological action: yes
Actions: antagonist

NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine

Organism class: human
UniProt ID: Q13224 Link_out

Gene: GRIN2B Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Pubmed

6. Glutamate [NMDA] receptor subunit epsilon-4

Pharmacological action: unknown
Actions: antagonist

NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine

Organism class: human
UniProt ID: O15399 Link_out

Gene: GRIN2D Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Pubmed

7. Alpha-7 nicotinic cholinergic receptor subunit

Pharmacological action: unknown
Actions: antagonist
Organism class: human
UniProt ID: Q693P7 Link_out

Gene: CHRFAM7A
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Pubmed

Comments

Drug created on July 31, 2007 07:10 / Updated on February 08, 2013 16:20