Compound: BENZOCTAMINE
SMILES: N(CC12c3c(cccc3)C(c4c1cccc4)CC2)C
InChIKey: GNRXCIONJWKSEA-UHFFFAOYSA-N
Synonyms: BENZOCTAMINE, 17243-39-9, Benzoctamina, Benzoctaminum, 9,10-Ethanoanthracene-9(10H)-methanamine, N-methyl-, 734MM7Y191, DTXSID4022654, RefChem:118268, DTXCID502654, N05BD01, methyl((tetracyclo(6.6.2.02,?.0?,1?)hexadeca-2,4,6,9,11,13-hexaen-1-yl)methyl)amine, Benzoktamina, 1-(9,10-Dihydro-9,10-ethanoanthracen-9-yl)-N-methylmethanamine, N-methyl-1-(1-tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaenyl)methanamine, N-Methyl-9,10-ethanoanthracene-9(10H)-methylamine, Benzoktamina [Polish], 9-(Methylaminomethyl)-9,10-dihydro-9,10-ethanoanthracene, 9,10-Ethanoanthracene-9(10H)-methylamine, N-methyl-, 9,10-dihydro, Benzoctamine [INN:BAN], Benzoctaminum [INN-Latin], Benzoctamina [INN-Spanish], BRN 2811058, 1-(9,10-ethanoanthracen-9(10H)-yl)-N-methylmethanamine, UNII-734MM7Y191, n-methyl-9,10-ethanoanthracene-9(10h)-methanamine, BENZOCTAMINE [MI], BENZOCTAMINE [INN], Ethanoanthracene-9(10H)-methylamine, N-methyl-, BENZOCTAMINE [WHO-DD], SCHEMBL115617, 9,10-Ethanoanthracene-9(10H)-methylamine, N-methyl-, orb1689652, CHEMBL2110603, SCHEMBL30726468, CHEBI:135017, GNRXCIONJWKSEA-UHFFFAOYSA-N, HY-A0171, DB09021, SB81277, DA-61579, NS00009094, N-Methyl-9,10-ethanoantrhacene-9(10H)-methylamine, Q4890786
Theoretical properties:
molecular_formula: C18H19N
molecular_weight: 249.3 g/mol
exact_mass: 249.151749610 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 1
rotatable_bond_count: 2
heavy_atom_count: 19
topological_polar_surface_area: 12 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 320-322
Descriptions:
pubchem: Benzoctamine is a member of anthracenes.
chembl: BENZOCTAMINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: Benzoctamine is a drug that possesses sedative and anxiolytic properties. Marketed as Tacitin by Ciba-Geigy, it is different from most sedative drugs because in most clinical trials it does not produce respiratory depression, but actually stimulates the respiratory system. As a result, when compared to other sedative and anxiolytic drugs such as benzodiazepines like diazepam, it is a safer form of tranquilizing. However, when co-administered with other drugs that cause respiratory depression, like morphine, it can cause increased respiratory depression.
Medically, benzoctamine is used as a treatment for anxious outpatients to control aggression, enuresis, fear, and minor social maladjustment in children. Its anxiolytic effects are most similar to diazepam, another anxiolytic, but unlike diazepam, benzoctamine has antagonistic effects on epinephrine and norepinephrine, and appears to increase serotonin levels. While little is understood about how it carries out its effects, studies point to reduced serotonin, epinephrine, and norepinephrine as partial causes of its pharmacologic and behavioral effects.
Animal studies have shown sedative hypnotic drugs tend to show dependency in animals, but benzoctamine has been shown to not be addictive. Other animal studies also point to the drug as a possible mechanism by which to reduce blood pressure through the adrenergic system.
Chemically, benzoctamine belongs to the class of compounds called dibenzobicyclo-octadienes. It is a tetracyclic compound, consisting of four rings in a three dimensional configuration, and is very closely related structurally to the tetracyclic antidepressant (TeCA) maprotiline, differing only in the length of their side chain.