1-methyl-16-azatetracyclo[7.6.1.02,7.010,15]hexadeca-2(7),3,5,10,12,14-hexaene

ID: ALA284237

Chembl Id: CHEMBL284237

Cas Number: 77086-21-6

PubChem CID: 180081

Product Number: M129502

Max Phase: Unknown

Molecular Formula: C16H15N

Molecular Weight: 221.30

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: MK-801 | DIZOCILPINE|77086-21-6|MK-801|Dizocilpine [INN]|MK 801|Lopac-M-107|Lopac-M-108|MK-801 (Dizocilpine)|Prestwick0_000109|(5S,10R)-5-methyl-10,11-dihydro-5H-5,10-epiminodibenzo[a,d][7]annulene|7PY8KH681I|CHEMBL284237|CHEBI:34725|MK801|(1S,9R)-1-methyl-16-azatetracyclo[7.6.1.02,7.010,15]hexadeca-2,4,6,10,12,14-hexaene|Dizocilpina|Dizocilpinum|(Rac)-Dizocilpine|(Rac)-MK-801|Dizocilpinum [INN-Latin]|Dizocilpina [INN-Spanish]|UNII-7PY8KH681I|HSDB 7641|dizocilpine-(+)|(+)MK-801|(-)-MK801|(+)-MK-Show More

Synonyms from Alternative Forms(2): Dizocilpine maleate | MK-801

Canonical SMILES:  C[C@]12N[C@H](Cc3ccccc31)c1ccccc12

Standard InChI:  InChI=1S/C16H15N/c1-16-13-8-4-2-6-11(13)10-15(17-16)12-7-3-5-9-14(12)16/h2-9,15,17H,10H2,1H3/t15-,16+/m1/s1

Standard InChI Key:  LBOJYSIDWZQNJS-CVEARBPZSA-N

Alternative Forms

  1. Parent:

    ALA284237

    DIZOCILPINE
  2. Alternative Forms:

Associated Targets(Human)

GRIN1 Tclin Glutamate [NMDA] receptor (933 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PRCP Tchem Lysosomal Pro-X carboxypeptidase (567 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SIGMAR1 Tclin Sigma opioid receptor (6358 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRM5 Tclin Muscarinic acetylcholine receptor M5 (4677 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GRIN1 Tclin Glutamate NMDA receptor; GRIN1/GRIN2B (726 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GRIN1 Tclin Glutamate NMDA receptor; GRIN1/GRIN2A (719 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NFKB1 Tclin Nuclear factor NF-kappa-B p105 subunit (1459 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TSHR Tclin Thyroid stimulating hormone receptor (29986 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ALOX12 Tchem Arachidonate 12-lipoxygenase (3262 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAPK1 Tchem MAP kinase ERK2 (25055 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HSD17B10 Tchem Endoplasmic reticulum-associated amyloid beta-peptide-binding protein (20669 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GRIN2A Tclin Glutamate [NMDA] receptor subunit epsilon 1 (112 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ATXN2 Tbio Ataxin-2 (54410 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GRIN2B Tclin Glutamate [NMDA] receptor subunit epsilon 2 (467 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MCF7 (126967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SK-BR-3 (5175 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BCHE Tclin Butyrylcholinesterase (7174 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC6 Tclin Histone deacetylase 6 (20808 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Fibroblast (163371 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
U2OS (164939 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HEK-293T (167025 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ABL1 Tclin Tyrosine-protein kinase ABL (18331 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AURKA Tchem Serine/threonine-protein kinase Aurora-A (10240 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BRD4 Tchem Bromodomain-containing protein 4 (13122 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BRPF1 Tchem Peregrin (2217 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CDK2 Tchem Cyclin-dependent kinase 2 (9050 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CSNK1D Tchem Casein kinase I delta (4546 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FGFR3 Tclin Fibroblast growth factor receptor 3 (7811 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GSK3B Tclin Glycogen synthase kinase-3 beta (11785 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TRIM24 Tchem Transcription intermediary factor 1-alpha (2087 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADGRF1 Tbio Adhesion G-protein coupled receptor F1 (1591 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GPR119 Tclin Glucose-dependent insulinotropic receptor (4762 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CX3CR1 Tchem C-X3-C chemokine receptor 1 (1686 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FFAR4 Tchem G-protein coupled receptor 120 (2999 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FPR2 Tchem Lipoxin A4 receptor (3472 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
S1PR1 Tclin Sphingosine 1-phosphate receptor Edg-1 (5806 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GLP1R Tclin Glucagon-like peptide 1 receptor (111429 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GPR35 Tchem G-protein coupled receptor 35 (2643 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AGTR1 Tclin Type-1 angiotensin II receptor (5176 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
C5AR1 Tclin C5a anaphylatoxin chemotactic receptor (2677 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
APLNR Tchem Apelin receptor (3301 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Grin1 Glutamate NMDA receptor (6467 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mus musculus (284745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Sigmar1 Sigma opioid receptor (1607 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Grin1 Glutamate (NMDA) receptor subunit zeta 1 (2166 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Grin2c Glutamate [NMDA] receptor subunit epsilon 3 (367 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Rattus norvegicus (775804 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Gerbillinae (442 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Chrm1 Muscarinic acetylcholine receptor (3770 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Oprm1 Mu opioid receptor (6060 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Gabrp GABA-A receptor; anion channel (5731 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Gabra2 GABA receptor alpha-2 subunit (87 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Cerebral cortex (17 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasmodium falciparum (966862 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Saccharomyces cerevisiae (19171 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Chrm1 Muscarinic acetylcholine receptor M1 (3437 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
pfk 6-phospho-1-fructokinase (7870 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Nos1 Nitric-oxide synthase, brain (2987 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Cortical neurone (598 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Brain (4256 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SIGMAR1 Sigma-1 receptor (3326 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Tmem97 Sigma intracellular receptor 2 (922 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
rep Replicase polyprotein 1ab (11336 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SARS-CoV-2 (38078 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: YesOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: YesAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 221.30Molecular Weight (Monoisotopic): 221.1204AlogP: 3.15#Rotatable Bonds:
Polar Surface Area: 12.03Molecular Species: NEUTRALHBA: 1HBD: 1
#RO5 Violations: HBA (Lipinski): 1HBD (Lipinski): 1#RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: 8.02CX LogP: 3.31CX LogD: 2.60
Aromatic Rings: 2Heavy Atoms: 17QED Weighted: 0.72Np Likeness Score: 1.10

References

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2. Monn JA, Thurkauf A, Mattson MV, Jacobson AE, Rice KC..  (1990)  Synthesis and structure-activity relationship of C5-substituted analogues of (+-)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine [(+-)-desmethyl-MK801]: ligands for the NMDA receptor-coupled phencyclidine binding site.,  33  (3): [PMID:2155320] [10.1021/jm00165a029]
3. Monn JA, Thurkauf A, Mattson MV, Jacobson AE, Rice KC..  (1990)  Synthesis and structure-activity relationship of C5-substituted analogues of (+-)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine [(+-)-desmethyl-MK801]: ligands for the NMDA receptor-coupled phencyclidine binding site.,  33  (3): [PMID:2155320] [10.1021/jm00165a029]
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5. Leeson PD, Carling RW, James K, Smith JD, Moore KW, Wong EH, Baker R..  (1990)  Role of hydrogen bonding in ligand interaction with the N-methyl-D-aspartate receptor ion channel.,  33  (5): [PMID:1691788] [10.1021/jm00167a005]
6. Leeson PD, Carling RW, James K, Smith JD, Moore KW, Wong EH, Baker R..  (1990)  Role of hydrogen bonding in ligand interaction with the N-methyl-D-aspartate receptor ion channel.,  33  (5): [PMID:1691788] [10.1021/jm00167a005]
7. Leeson PD, Carling RW, James K, Smith JD, Moore KW, Wong EH, Baker R..  (1990)  Role of hydrogen bonding in ligand interaction with the N-methyl-D-aspartate receptor ion channel.,  33  (5): [PMID:1691788] [10.1021/jm00167a005]
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11. Kumar V, Carabateas PM, Dority JA, Earley WG, Mallamo JP, Subramanyam C, Aimone LD, Ault B, DeHaven Hudkins DL, Miller MS..  (1995)  Novel NMDA antagonists: replacement of the pyridinium ring of 6,11-ethanobenzo[b]quinolizinium cations with heteroisoquinolinium cations.,  38  (10): [PMID:7752207] [10.1021/jm00010a028]
12. Moe ST, Shimizu SM, Smith DL, Van Wagenen BC, DelMar EG, Balandrin MF, Chien Y, Raszkiewicz JL, Artman LD, Mueller AL, Lobkovsky E, Clardy J..  (1999)  Synthesis, biological activity, and absolute stereochemical assignment of NPS 1392: a potent and stereoselective NMDA receptor antagonist.,  (14): [PMID:10450953] [10.1016/s0960-894x(99)00317-0]
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14. Bigge CF, Malone TC, Hays SJ, Johnson G, Novak PM, Lescosky LJ, Retz DM, Ortwine DF, Probert AW, Coughenour LL..  (1993)  Synthesis and pharmacological evaluation of 4a-phenanthrenamine derivatives acting at the phencyclidine binding site of the N-methyl-D-aspartate receptor complex.,  36  (14): [PMID:8336337] [10.1021/jm00066a007]
15. Goodnow RA, Bukownik R, Nakanishi K, Usherwood PN, Eldefrawi AT, Anis NA, Eldefrawi ME..  (1991)  Synthesis and binding of [125I2]philanthotoxin-343, [125I2]philanthotoxin-343-lysine, and [125I2]philanthotoxin-343-arginine to rat brain membranes.,  34  (8): [PMID:1652018] [10.1021/jm00112a012]
16. Moe ST, Smith DL, DelMar EG, Shimizu SM, Van Wagenen BC, Balandrin MF, Chien YE, Raszkiewicz JL, Artman LD, White HS, Mueller AL..  (2000)  Chiral synthesis and pharmacological evaluation of NPS 1407: a potent, stereoselective NMDA receptor antagonist.,  10  (21): [PMID:11078190] [10.1016/s0960-894x(00)00470-4]
17. Subramanyam C, Mallamo JP, Pilling GM, Earley WG, Carabateas PM, Wetzel JR, DeHaven-Hudkins D, Allen T, Kullnig RK..  (1995)  Synthesis and evaluation of 6,11-ethanohexahydrobenzo[b]quinolizidines: a new class of noncompetitive N-methyl-D-aspartate antagonists.,  38  (13): [PMID:7608913] [10.1021/jm00013a025]
18. Linders JT, Monn JA, Mattson MV, George C, Jacobson AE, Rice KC..  (1993)  Synthesis and binding properties of MK-801 isothiocyanates; (+)-3-isothiocyanato-5-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten- 5,10-imine hydrochloride: a new, potent and selective electrophilic affinity ligand for the NMDA receptor-coupled phencyclidine binding site.,  36  (17): [PMID:8355251] [10.1021/jm00069a008]
19. Subramanyam C, Mallamo JP, Dority JA, Earley WG, Kumar V, Aimone LD, Ault B, Miller MS, Luttinger DA, DeHaven-Hudkins DL..  (1995)  Discovery of 6,11-ethano-12,12-diaryl-6,11-dihydrobenzo[b]quinolizinium cations, a novel class of N-methyl-D-aspartate antagonists.,  38  (1): [PMID:7837234] [10.1021/jm00001a006]
20. Jimonet P, Audiau F, Barreau M, Blanchard JC, Boireau A, Bour Y, Coléno MA, Doble A, Doerflinger G, Huu CD, Donat MH, Duchesne JM, Ganil P, Guérémy C, Honor E, Just B, Kerphirique R, Gontier S, Hubert P, Laduron PM, Le Blevec J, Meunier M, Miquet JM, Nemecek C, Mignani S..  (1999)  Riluzole series. Synthesis and in vivo "antiglutamate" activity of 6-substituted-2-benzothiazolamines and 3-substituted-2-imino-benzothiazolines.,  42  (15): [PMID:10425092] [10.1021/jm980202u]
21. Martin LL, Lee GE, Lee TB, Rush DK, Wilmot CA, Paulus E, Elben U, Grome JJ, Porsche-Wiebking E, Rudolphi KA..  (1994)  Synthesis, resolution, and SAR of (+/-)-2-amino-N-methyl-alpha-(3-methyl-2-thienyl)benzeneethanamine++ + and related analogs as noncompetitive NMDA antagonists with neuroprotective properties.,  37  (19): [PMID:7932522] [10.1021/jm00045a004]
22. Earley WG, Kumar V, Mallamo JP, Subramanyam C, Dority JA, Miller MS, DeHaven-Hudkins DL, Aimone LD, Kelly MD, Ault B..  (1995)  Novel benzo[b]quinolizinium cations as uncompetitive N-methyl-D-aspartic acid (NMDA) antagonists: the relationship between log D and agonist independent (closed) NMDA channel block.,  38  (18): [PMID:7658445] [10.1021/jm00018a018]
23. Reuman M, Mallamo JP, DeHaven-Hudkins DL.  (1995)  Synthesis and binding affinity of 2,3,3a,4,9,9a-hexahydro-9,4-(iminomethano)-1H-benz[f]indenes. Ligands for the PCP site of the NMDA receptor,  (4): [10.1016/0960-894X(95)00038-U]
24. Kroemer RT, Koutsilieri E, Hecht P, Liedl KR, Riederer P, Kornhuber J..  (1998)  Quantitative analysis of the structural requirements for blockade of the N-methyl-D-aspartate receptor at the phencyclidine binding site.,  41  (3): [PMID:9464369] [10.1021/jm9704412]
25. Kroemer RT, Koutsilieri E, Hecht P, Liedl KR, Riederer P, Kornhuber J..  (1998)  Quantitative analysis of the structural requirements for blockade of the N-methyl-D-aspartate receptor at the phencyclidine binding site.,  41  (3): [PMID:9464369] [10.1021/jm9704412]
26. Newman AH, Bevan K, Bowery N, Tortella FC..  (1992)  Synthesis and evaluation of 3-substituted 17-methylmorphinan analogs as potential anticonvulsant agents.,  35  (22): [PMID:1433216] [10.1021/jm00100a019]
27. Hu LY, Guo J, Magar SS, Fischer JB, Burke-Howie KJ, Durant GJ..  (1997)  Synthesis and pharmacological evaluation of N-(2,5-disubstituted phenyl)-N'-(3-substituted phenyl)-N'-methylguanidines as N-methyl-D-aspartate receptor ion-channel blockers.,  40  (26): [PMID:9435897] [10.1021/jm970459c]
28. Kimes AS, Wilson AA, Scheffel U, Campbell BG, London ED..  (1992)  Radiosynthesis, cerebral distribution, and binding of [125I]-1-(p-iodophenyl)-3-(1-adamantyl)guanidine, a ligand for sigma binding sites.,  35  (25): [PMID:1469697] [10.1021/jm00103a005]
29. Moriarty RM, Enache LA, Zhao L, Gilardi R, Mattson MV, Prakash O..  (1998)  Rigid phencyclidine analogues. Binding to the phencyclidine and sigma 1 receptors.,  41  (4): [PMID:9484497] [10.1021/jm970059p]
30. Shuto S, Ono S, Hase Y, Ueno Y, Noguchi T, Yoshii K, Matsuda A..  (1996)  Synthesis and biological activity of conformationally restricted analogs of milnacipran: (1S,2R)-1-phenyl-2-[(S)-1-aminopropyl]-N,N-diethylcyclopropanecarboxami de, an efficient noncompetitive N-methyl-D-aspartic acid receptor antagonist.,  39  (24): [PMID:8941398] [10.1021/jm960495w]
31. Malone TC, Ortwine DF, Johnson G, Probert AW.  (1993)  Synthesis and biological activity of conformationally constrained 4a-phenanthreneamine derivatives as noncompetitive NMDA antagonists,  (1): [10.1016/S0960-894X(00)80090-6]
32. Hays SJ, Novak PM, Ortwine DF, Bigge CF, Colbry NL, Johnson G, Lescosky LJ, Malone TC, Michael A, Reily MD..  (1993)  Synthesis and pharmacological evaluation of hexahydrofluorenamines as noncompetitive antagonists at the N-methyl-D-aspartate receptor.,  36  (6): [PMID:8459395] [10.1021/jm00058a002]
33. Carling RW, Leeson PD, Moseley AM, Smith JD, Saywell K, Tricklebank MD, Kemp JA, Marshall GR, Foster AC, Grimwood S.  (1993)  Anticonvulsant activity of glycine-site NMDA antagonists. 2. trans 2-carboxy-4-substituted tetrahydroquinolines.,  (1): [10.1016/S0960-894X(00)80093-1]
34. Thompson WJ, Anderson PS, Britcher SF, Lyle TA, Thies JE, Magill CA, Varga SL, Schwering JE, Lyle PA, Christy ME..  (1990)  Synthesis and pharmacological evaluation of a series of dibenzo[a,d]cycloalkenimines as N-methyl-D-aspartate antagonists.,  33  (2): [PMID:1688947] [10.1021/jm00164a052]
35. Thompson WJ, Anderson PS, Britcher SF, Lyle TA, Thies JE, Magill CA, Varga SL, Schwering JE, Lyle PA, Christy ME..  (1990)  Synthesis and pharmacological evaluation of a series of dibenzo[a,d]cycloalkenimines as N-methyl-D-aspartate antagonists.,  33  (2): [PMID:1688947] [10.1021/jm00164a052]
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