(1S,9R)-1-methyl-16-azatetracyclo[7.6.1.02,7.010,15]hexadeca-2,4,6,10(15),11,13-hexaene; (2Z)-but-2-enedioic acid

• ChemBase ID: 133281
• Molecular Formular: C20H19NO4
• Molecular Mass: 337.36916
• Monoisotopic Mass: 337.13140809
• SMILES: C[C@@]12c3ccccc3C[C@H](N1)c1c2cccc1.C(=C\C(=O)O)\C(=O)O
• Canonical SMILES: C[C@]12N[C@H](c3c2cccc3)Cc2c1cccc2.OC(=O)/C=C\C(=O)O
• InChI: InChI=1S/C16H15N.C4H4O4/c1-16-13-8-4-2-6-11(13)10-15(17-16)12-7-3-5-9-14(12)16;5-3(6)1-2-4(7)8/h2-9,15,17H,10H2,1H3;1-2H,(H,5,6)(H,7,8)/b;2-1-/t15-,16+;/m1./s1
• InChIKey: QLTXKCWMEZIHBJ-PJGJYSAQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,9R)-1-methyl-16-azatetracyclo[7.6.1.0^2,^7.0^1^0,^1^5]hexadeca-2,4,6,10(15),11,13-hexaene; (2Z)-but-2-enedioic acid
• IUPAC Traditional name: (1S,9R)-1-methyl-16-azatetracyclo[7.6.1.0^2,^7.0^1^0,^1^5]hexadeca-2,4,6,10(15),11,13-hexaene; maleic acid
• Synonyms: (5S,10R)-(+)-5-Methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine hydrogen maleate; Dizocilpine hydrogen maleate; (+)-MK-801 hydrogen maleate

Database IDs

• CAS Number: 77086-22-7
• EC Number: 278-614-5
• MDL Number: MFCD00082465
• PubChem SID: 162227558; 24277988
• PubChem CID: 6420042

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 0.44438058
• LogD (pH = 7.4): 2.0864916
• Log P: 3.3085747
• Molar Refractivity: 69.9624 cm^3
• Polarizability: 27.347187 Å^3
• Polar Surface Area: 12.03 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.1 M HCl: soluble; DMSO: >20 mg/mL; ethanol: soluble; H2O: soluble6 mg/mL
• Apperance: white powder
• Optical Rotation: [α]25/D +117°, c = 1 in methanol(lit.)

Safety Information

• RTECS: HP1093575
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... GRIN1(2902), GRIN2A(2903), GRIN2B(2904), GRIN2C(2905), GRIN2D(2906), GRIN3A(116443), GRIN3B(116444), GRINA(2907)mouse ... GRIN1(14810), GRIN2A(14811), GRIN2B(14812), GRIN2C(14813), GRIN2D(14814), GRIN3A(242443), GRIN3B(170483), GRINA(66168)rat ... GRIN1(24408), GRIN2A(24409), GRIN2B(24410), GRIN2C(24411), GRIN2D(24412), GRIN3A(191573), GRIN3B(170796), GRINA(266668)

DETAILS

Sigma Aldrich - M107

Biochem/physiol Actions
Highly potent and selective non-competitive NMDA glutamate receptor antagonist that acts at the NMDA receptor-operated ion channel as an open channel blocker. Inhibits behavioral sensitization to psychostimulants and ethanol.