DT-Web

DB01520 - Tenocyclidine


Identification
Name Tenocyclidine
Accession Number DB01520
Type small molecule
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
MOL SDF PDB SMILES InChI
Categories (*)
Molecular Weight 249.415
Groups illicit
Monoisotopic Weight 249.155120431
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.
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 ?7-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
Protein binding Not Available
Biotransformation Not Available
Route of elimination Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Interactions
Drug Interactions Not Available
Food Interactions Not Available

Targets


Glutamate [NMDA] receptor subunit 3A
Name Glutamate [NMDA] receptor subunit 3A
Gene Name GRIN3A
Pharmacological action yes
Actions antagonist
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
DTHybrid score 0.5505
Glutamate [NMDA] receptor subunit 3B
Name Glutamate [NMDA] receptor subunit 3B
Gene Name GRIN3B
Pharmacological action yes
Actions antagonist
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
DTHybrid score 0.3468
Glutamate [NMDA] receptor subunit epsilon-1
Name Glutamate [NMDA] receptor subunit epsilon-1
Gene Name GRIN2A
Pharmacological action yes
Actions antagonist
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
DTHybrid score 0.5038
Glutamate [NMDA] receptor subunit epsilon-3
Name Glutamate [NMDA] receptor subunit epsilon-3
Gene Name GRIN2C
Pharmacological action yes
Actions antagonist
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
DTHybrid score 0.3783
Glutamate [NMDA] receptor subunit epsilon-2
Name Glutamate [NMDA] receptor subunit epsilon-2
Gene Name GRIN2B
Pharmacological action yes
Actions antagonist
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
DTHybrid score 0.5062
Glutamate [NMDA] receptor subunit epsilon-4
Name Glutamate [NMDA] receptor subunit epsilon-4
Gene Name GRIN2D
Pharmacological action unknown
Actions antagonist
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
DTHybrid score 0.4262
Alpha-7 nicotinic cholinergic receptor subunit
Name Alpha-7 nicotinic cholinergic receptor subunit
Gene Name CHRFAM7A
Pharmacological action unknown
Actions antagonist
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
DTHybrid score 0.4343

Predictions


Id Partner name Gene Name Score
6030 Cytochrome P450 2B6 CYP2B6 0.1592
401 Glutamate [NMDA] receptor subunit zeta-1 GRIN1 0.1376
6016 Cytochrome P450 2C19 CYP2C19 0.1172
4512 Cytochrome P450 3A4 CYP3A4 0.1104
6013 Cytochrome P450 2E1 CYP2E1 0.0818
341 5-hydroxytryptamine 3 receptor HTR3A 0.0795
696 Kappa-type opioid receptor OPRK1 0.0718
198 Sodium channel protein type 10 subunit alpha SCN10A 0.0653
4119 Cytochrome P450 2D6 CYP2D6 0.0621
458 Neuronal acetylcholine receptor subunit alpha-10 CHRNA10 0.0589
5718 Cytochrome P450 2A6 CYP2A6 0.0556
540 Sodium-dependent noradrenaline transporter SLC6A2 0.054
3923 Cholinesterase BCHE 0.0538
6144 Solute carrier family 22 member 2 SLC22A2 0.0527
587 Serum albumin ALB 0.0474
1181 Alpha-1-acid glycoprotein 1 ORM1 0.0472
51 Muscarinic acetylcholine receptor M3 CHRM3 0.045
831 D(2) dopamine receptor DRD2 0.0413
617 Muscarinic acetylcholine receptor M2 CHRM2 0.0386
482 Glycine receptor subunit alpha-1 GLRA1 0.0377
103 Muscarinic acetylcholine receptor M1 CHRM1 0.0372
916 Metabotropic glutamate receptor 1 GRM1 0.0333
174 Sigma 1-type opioid receptor SIGMAR1 0.0331
492 Histamine H1 receptor HRH1 0.0322
593 Proton-coupled amino acid transporter 1 SLC36A1 0.0297
4057 Glycine N-acyltransferase GLYAT 0.0277
4061 Peroxisomal sarcosine oxidase PIPOX 0.0277
4059 Glycine N-acyltransferase-like protein 1 GLYATL1 0.0277
4058 Glycine N-acyltransferase-like protein 2 GLYATL2 0.0277
4056 N-arachidonyl glycine receptor GPR18 0.0277
4055 Bile acid CoA:amino acid N-acyltransferase BAAT 0.0277
4060 Vesicular inhibitory amino acid transporter SLC32A1 0.0277
1088 5-aminolevulinate synthase, erythroid-specific, mitochondrial ALAS2 0.0277
1236 Sodium- and chloride-dependent glycine transporter 1 SLC6A9 0.0277
1466 Glycyl-tRNA synthetase GARS 0.0277
4062 Sodium- and chloride-dependent glycine transporter 2 SLC6A5 0.0277
1768 Guanine nucleotide-binding protein G(I)/G(S)/G(O) gamma-2 subunit GNG2 0.0271
1268 Neuropeptide S receptor NPSR1 0.0271
1571 G protein-activated inward rectifier potassium channel 1 KCNJ3 0.0271
1581 G protein-activated inward rectifier potassium channel 2 KCNJ6 0.0271
6151 Monocarboxylate transporter 10 SLC16A10 0.0246
4757 Cytochrome P450 2C9 CYP2C9 0.0245
922 Glutamate receptor 4 GRIA4 0.0245
924 Glutamate receptor, ionotropic kainate 3 GRIK3 0.0245
919 Glutamate receptor, ionotropic kainate 4 GRIK4 0.0245
920 Glutamate receptor, ionotropic kainate 5 GRIK5 0.0245
4018 Glutamate receptor delta-2 subunit GRID2 0.0245
4027 Glutamate receptor delta-1 subunit GRID1 0.0245
4025 Mitochondrial glutamate carrier 1 SLC25A22 0.0245
4024 Mitochondrial glutamate carrier 2 SLC25A18 0.0245
4022 Glutamate--ammonia ligase domain-containing protein 1 LGSN 0.0245
4021 Probable glutamyl-tRNA synthetase, mitochondrial EARS2 0.0245
4026 Aspartyl aminopeptidase DNPEP 0.0245
4016 Excitatory amino acid transporter 5 SLC1A7 0.0245
4023 N-acetylglutamate synthase, mitochondrial NAGS 0.0245
1912 Excitatory amino acid transporter 1 SLC1A3 0.0245
4019 Excitatory amino acid transporter 4 SLC1A6 0.0245
664 Glutamate decarboxylase 2 GAD2 0.0245
3890 Glutamate decarboxylase 2 GAD2 0.0245
1047 Excitatory amino acid transporter 2 SLC1A2 0.0245
915 Delta 1-pyrroline-5-carboxylate synthetase ALDH18A1 0.0245
4020 Glutamyl aminopeptidase ENPEP 0.0245
925 Metabotropic glutamate receptor 4 GRM4 0.0245
927 Metabotropic glutamate receptor 8 GRM8 0.0245
926 Metabotropic glutamate receptor 7 GRM7 0.0245
4017 5-oxoprolinase OPLAH 0.0245
820 Glycine receptor subunit alpha-2 GLRA2 0.0238
467 Delta-type opioid receptor OPRD1 0.0236
6073 Potassium channel subfamily K member 9 KCNK9 0.0233
6072 Potassium channel subfamily K member 3 KCNK3 0.0233
575 2-amino-3-ketobutyrate coenzyme A ligase, mitochondrial GCAT 0.0226
455 5-aminolevulinate synthase, nonspecific, mitochondrial ALAS1 0.0226
681 Glycine dehydrogenase [decarboxylating], mitochondrial GLDC 0.0226
847 Mu-type opioid receptor OPRM1 0.0226
62 Glycine receptor subunit beta GLRB 0.0222
824 Sodium-dependent serotonin transporter SLC6A4 0.0219
830 Glutamate dehydrogenase 2, mitochondrial GLUD2 0.0217
668 Glutamate--cysteine ligase regulatory subunit GCLM 0.0209
4054 Glycine cleavage system H protein, mitochondrial GCSH 0.0209
3984 Probable glutamyl-tRNA(Gln) amidotransferase subunit B, mitochondrial PET112L 0.0208
355 GMP synthase [glutamine-hydrolyzing] GMPS 0.0208
4353 GMP synthase [glutamine-hydrolyzing] guaA 0.0208
5 Glutaminase liver isoform, mitochondrial GLS2 0.0208
917 Glutaminase kidney isoform, mitochondrial GLS 0.0208
3991 Glutamine-dependent NAD(+) synthetase NADSYN1 0.0208
3982 Phosphoribosylformylglycinamidine synthase PFAS 0.0208
5261 Phosphoribosylformylglycinamidine synthase purL 0.0208
3884 SHMT2 protein SHMT2 0.0207
3901 SHMT2 protein SHMT2 0.0207
3885 Hypothetical protein DKFZp686P09201 DKFZp686P09201 0.0207
3879 Serine hydroxymethyltransferase 2 Not Available 0.0207
321 Serine hydroxymethyltransferase, mitochondrial SHMT2 0.0207
665 Phosphoserine aminotransferase PSAT1 0.0203
4652 Phosphoserine aminotransferase serC 0.0203
801 Kynurenine/alpha-aminoadipate aminotransferase mitochondrial AADAT 0.0202
3895 Kynurenine--oxoglutarate transaminase 3 CCBL2 0.0202
420 Glutamate decarboxylase 1 GAD1 0.0202
3900 Glutamate decarboxylase 1 GAD1 0.0202
625 Glutamate carboxypeptidase 2 FOLH1 0.0202
462 Intermediate conductance calcium-activated potassium channel protein 4 KCNN4 0.0199
382 Glutamate receptor, ionotropic kainate 1 GRIK1 0.0199
114 Alanine--glyoxylate aminotransferase 2, mitochondrial AGXT2 0.0198
207 Glutathione synthetase GSS 0.0196
5269 Glutathione synthetase gshB 0.0196
411 Glycine N-methyltransferase GNMT 0.0195
241 Calcium-transporting ATPase type 2C member 1 ATP2C1 0.0191
448 Vitamin K-dependent gamma-carboxylase GGCX 0.0191
383 Glycine amidinotransferase, mitochondrial GATM 0.019
590 5-hydroxytryptamine 2C receptor HTR2C 0.019
186 Glutamate--cysteine ligase catalytic subunit GCLC 0.0187
461 Glycine receptor subunit alpha-3 GLRA3 0.0187
1671 Excitatory amino acid transporter 3 SLC1A1 0.0186
201 Glutamate dehydrogenase 1, mitochondrial GLUD1 0.0186
3877 Growth-inhibiting protein 18 GIG18 0.0185
713 Sodium-dependent dopamine transporter SLC6A3 0.0184
537 ATP synthase delta chain, mitochondrial ATP5D 0.0182
923 Glutamate receptor 3 GRIA3 0.0181
763 Tyrosine aminotransferase TAT 0.0181
5493 Tyrosine aminotransferase Not Available 0.0181
1588 Multidrug resistance protein 1 ABCB1 0.0178
349 Serine--pyruvate aminotransferase AGXT 0.0178
3904 Alanine aminotransferase 2 GPT2 0.0178
735 Alanine aminotransferase 1 GPT 0.0178
773 Folylpolyglutamate synthase, mitochondrial FPGS 0.0176
914 Formimidoyltransferase-cyclodeaminase FTCD 0.0174
4096 Metabotropic glutamate receptor 3 GRM3 0.0174
1362 Metabotropic glutamate receptor 2 GRM2 0.0174
426 Aspartate aminotransferase, mitochondrial GOT2 0.0174
367 Serine hydroxymethyltransferase, cytosolic SHMT1 0.0172
559 NADH-ubiquinone oxidoreductase chain 1 MT-ND1 0.0171
83 Alpha-aminoadipic semialdehyde synthase, mitochondrial AASS 0.0168
610 Calcium-activated potassium channel subunit alpha 1 KCNMA1 0.0167
242 Asparagine synthetase [glutamine-hydrolyzing] ASNS 0.0166
586 Aspartate aminotransferase, cytoplasmic GOT1 0.0166
2207 Rhodopsin RHO 0.0165
210 Bifunctional aminoacyl-tRNA synthetase [Includes: Glutamyl-tRNA synthetase EPRS 0.0163
705 Glutamate receptor 1 GRIA1 0.0162
574 Branched-chain-amino-acid aminotransferase, cytosolic BCAT1 0.0157
2178 Metabotropic glutamate receptor 5 GRM5 0.0157
795 Branched-chain-amino-acid aminotransferase, mitochondrial BCAT2 0.0155
3426 Glutamine synthetase glnA 0.0155
3987 Glutamine synthetase GLUL 0.0155
33 Cystine/glutamate transporter SLC7A11 0.0152
280 4-aminobutyrate aminotransferase, mitochondrial ABAT 0.0149
872 Gamma-aminobutyric-acid receptor subunit alpha-1 GABRA1 0.0142
813 Neuronal acetylcholine receptor subunit alpha-2 CHRNA2 0.0136
694 Matrix protein 2 M 0.0121
738 Monocarboxylate transporter 1 SLC16A1 0.0121
918 Glutamate receptor, ionotropic kainate 2 GRIK2 0.0119
6107 Cytochrome P450 3A7 CYP3A7 0.0115
5251 Carbonyl reductase [NADPH] 1 CBR1 0.011
4118 Cytochrome P450 3A5 CYP3A5 0.0108
921 Glutamate receptor 2 GRIA2 0.0107
4200 Cytochrome P450 1A2 CYP1A2 0.0101
427 Substance-P receptor TACR1 0.0098
6024 Cytochrome P450 1A1 CYP1A1 0.0095
4924 Cytochrome P450 2C8 CYP2C8 0.0092
3876 Aromatic-L-amino-acid decarboxylase DDC 0.009
638 D(3) dopamine receptor DRD3 0.0084
6018 UDP-glucuronosyltransferase 1-9 UGT1A9 0.0084
23 D(1A) dopamine receptor DRD1 0.0075
502 5-hydroxytryptamine 2A receptor HTR2A 0.007
3939 Amine oxidase [flavin-containing] B MAOB 0.0067
319 Opioid receptor, sigma 1 OPRS1 0.0066
6145 Solute carrier family 22 member 1 SLC22A1 0.0057
251 Alcohol dehydrogenase 1A ADH1A 0.0054
20 Prostaglandin G/H synthase 1 PTGS1 0.0048
444 Alcohol dehydrogenase 1B ADH1B 0.0047
468 Cytochrome P450 4A11 CYP4A11 0.0045
517 Alcohol dehydrogenase 1C ADH1C 0.0041
6106 Cytochrome P450 2C18 CYP2C18 0.0035
3811 Cytochrome P450 19A1 CYP19A1 0.0033
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