Compound: DIZOCILPINE
SMILES: N1[C@]2(c3c(cccc3)C[C@@H]1c4ccccc24)C
InChIKey: LBOJYSIDWZQNJS-CVEARBPZSA-N
Synonyms: DIZOCILPINE, 77086-21-6, Dizocilpina, Dizocilpinum, 7PY8KH681I, DTXSID3048447, CHEBI:34725, 5H-Dibenzo(a,d)cyclohepten-5,10-imine, 10,11-dihydro-5-methyl-, (5S)-, RefChem:135282, DTXCID3028421, Dizocilpine [INN], (5S,10R)-5-methyl-10,11-dihydro-5H-5,10-epiminodibenzo[a,d][7]annulene, Lopac-M-107, Lopac-M-108, MK-801 (Dizocilpine), Prestwick0_000109, (1S,9R)-1-methyl-16-azatetracyclo[7.6.1.02,7.010,15]hexadeca-2,4,6,10,12,14-hexaene, CHEMBL284237, MFCD06412575, (Rac)-Dizocilpine, (+)-MK-801, (Rac)-MK-801, Dizocilpinum [INN-Latin], Dizocilpina [INN-Spanish], UNII-7PY8KH681I, HSDB 7641, dizocilpine-(+), (+)MK-801, (+/-)-MK801, Dizocilpine free base?, DIZOCILPINE [MI], Prestwick1_000109, Prestwick2_000109, Prestwick3_000109, DIZOCILPINE [HSDB], Biomol-NT_000210, Lopac0_000872, SCHEMBL34528, BSPBio_000098, DIZOCILPINE [WHO-DD], SPBio_002037, BPBio1_000108, BPBio1_001272, GTPL2403, orb1300929, 10,11-Dihydro-5-methyl-5H-dibenzo[a,d]cyclohepten-5,10-imine.(MK-801), SCHEMBL29358391, (5S,10R)-(+)-5-methyl-10,11-dihydro-5Hdibenzo[a,d]cyclohepten-5,10-imine, (5S,10S)-(+)-5-methyl-10,11-dihydro-5Hdibenzo[a,d]cyclohepten-5,10-imine, 1-methyl-16-azatetracyclo[7.6.1.02,7.010,15]hexadeca-2(7),3,5,10(15),11,13-hexaene, 1-methyl-16-azatetracyclo[7.6.1.02,7.010,15]hexadeca-2(7),3,5,10,12,14-hexaene, 1-methyl-16-azatetracyclo[7.6.1.02,7.010,15]hexadeca-2,4,6,10(15),11,13-hexaene, CHEBI:132408, LBOJYSIDWZQNJS-CVEARBPZSA-N, HMS3267C15, (+)-1-methyl-16-azatetracyclo[7.6.1.02,7.010,15]hexadeca-2(7),3,5,10(15),11,13-hexaene, (+/-) MK-8011-methyl-(9R,1R)-16-azatetracyclo[7.6.1.02,7.010,15]hexadeca-2(7),3,5,10(15),11,13-hexaene, (+/-)-1-methyl-16-azatetracyclo[7.6.1.02,7.010,15]hexadeca-2(7),3,5,10(15),11,13-hexaene, (-)-1-methyl-16-azatetracyclo[7.6.1.02,7.010,15]hexadeca-2(7),3,5,10(15),11,13-hexaene, (1S,9R)-1-methyl-16-azatetracyclo[7.6.1.0^{2,7}.0^{10,15}]hexadeca-2(7),3,5,10(15),11,13-hexaene, (1S,9R)-1-methyl-16-azatetracyclo[7.6.1.0^{2,7}.0^{10,15}]hexadeca-2,4,6,10(15),11,13-hexaene, (Dizocilpine)1-methyl-16-azatetracyclo[7.6.1.02,7.010,15]hexadeca-2(7),3,5,10(15),11,13-hexaene, (MK-801)1-methyl-16-azatetracyclo[7.6.1.02,7.010,15]hexadeca-2(7),3,5,10(15),11,13-hexaene, 1-methyl-16-azatetracyclo[7.6.1.02,7.010,15]hexadeca-2(7),3,5,10(15),11,13-hexaene(MK-801), CDA08621, EX-A1701, BDBM50030386, BDBM50344263, HY-15084B, PDSP1_000178, PDSP1_001281, PDSP2_000177, PDSP2_001265, AKOS026673945, AT27821, CCG-204954, SDCCGSBI-0050847.P002, NCGC00015627-01, NCGC00015627-02, NCGC00016935-04, NCGC00016935-05, NCGC00016935-06, NCGC00016935-19, NCGC00024876-02, AC-35306, DA-52593, SY365024, TS-09284, CS-0020032, NS00076277, SW197022-4, F601071, Q4386371, BRD-K58930050-001-01-1, BRD-K58930050-001-05-2, BRD-K58930050-050-03-4, BRD-K58930050-050-15-8, (+)-10,11-DIHYDRO-5-METHYL-5H-DIBENZO(A,D)CYCLOHEPTEN-5,10-IMINE, 5H-DIBENZO(A,D)CYCLOHEPTEN-5,10-IMINE, 10,11-DIHYDRO-5-METHYL-, (+)-, 5H-Dibenzo[a,d]cyclohepten-5,10-imine, 10,11-dihydro-5-methyl-, (5S,10R)-, (1S)-1-methyl-16-azatetracyclo[7.6.1.0^{2,7}.0^{10,15}]hexadeca-2(7),3,5,10,12,14-hexaene; (2Z)-but-2-enedioate, (1S,9R)-1-methyl-16-azatetracyclo[7.6.1.0?,?.0??,??]hexadeca-2,4,6,10,12,14-hexaene, 1-methyl-16-azatetracyclo[7.6.1.02,7.010,15]hexadeca-2(7),3,5,10(15),11,13-hexaene maleate((+)-MK801), 5H-Dibenzo[a,d]cyclohepten-5,10-imine, 10,11-dihydro-5-methyl-, (5S)-, (2Z)-2-butenedioate (1:1)
Theoretical properties:
molecular_formula: C16H15N
molecular_weight: 221.30 g/mol
exact_mass: 221.120449483 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 1
rotatable_bond_count: 0
heavy_atom_count: 17
topological_polar_surface_area: 12 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: White solid from cyclohexane
color: White solid from cyclohexane
melting_point: 68.5-69 °C
Descriptions:
{"pubchem": "Dizocilpine is an organic heterotetracyclic compound that is 1-methyl-8-azabicyclo[3.2.1]octane ortho-fused to two benzene rings at positions 2-3 and 6-7 (the 5S,10R-stereoisomer). It is a non-competitive antagonist of the N-methyl-D-aspartate (NMDA) receptor and affects cognitive function, learning, and memory. It has a role as an anticonvulsant, an anaesthetic, a nicotinic antagonist, a NMDA receptor antagonist and a neuroprotective agent. It is a tetracyclic antidepressant and a secondary amino compound. It is a conjugate base of a dizocilpine(1+).", "chebi": "An organic heterotetracyclic compound that is 1-methyl-8-azabicyclo[3.2.1]octane <em>ortho</em>-fused to two benzene rings at positions 2-3 and 6-7 (the 5<i>S</i>,10<i>R</i>-stereoisomer). It is a non-competitive antagonist of the <em>N</em>-methyl-<small>D</small>-aspartate (NMDA) receptor and affects cognitive function, learning, and memory.", "chembl": "DIZOCILPINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.", "wikipedia": "Dizocilpine (INN), also known as MK-801, is a pore blocker of the NMDA receptor, a glutamate receptor, discovered by a team at Merck in 1982. Glutamate is the brain's primary excitatory neurotransmitter. The channel is normally blocked with a magnesium ion and requires depolarization of the neuron to remove the magnesium and allow the glutamate to open the channel, causing an influx of calcium, which then leads to subsequent depolarization. Dizocilpine binds inside the ion channel of the receptor at several of PCP's binding sites thus preventing the flow of ions, including calcium (Ca2+), through the channel. Dizocilpine blocks NMDA receptors in a use- and voltage-dependent manner, since the channel must open for the drug to bind inside it. The drug acts as a potent anti-convulsant and probably has dissociative anesthetic properties, but it is not used clinically for this purpose because of the discovery of brain lesions, called Olney's lesions (see below), in laboratory rats. Dizocilpine is also associated with a number of negative side effects, including cognitive disruption and psychotic-spectrum reactions. It inhibits the induction of long term potentiation and has been found to impair the acquisition of difficult, but not easy, learning tasks in rats and primates. Because of these effects of dizocilpine, the NMDA receptor pore blocker ketamine is used instead as a dissociative anesthetic in human medical procedures. While ketamine may also trigger temporary psychosis in certain individuals, its short half-life and lower potency make it a much safer clinical option. However, dizocilpine is the most frequently used uncompetitive NMDA receptor antagonist in animal models to mimic psychosis for experimental purposes.\nDizocilpine has also been found to act as a nicotinic acetylcholine receptor antagonist. It has been shown to bind to and inhibit the serotonin and dopamine transporters as well."}