Benzoctamine

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.

Benzoctamine
Clinical data
Trade namesTacitin
Routes of
administration
Oral, intravenous
ATC code
Legal status
Legal status
  • BR: Class C1 (Other controlled substances)
  • In general: legal
Pharmacokinetic data
Bioavailability100% for intravenous, 90% for oral
MetabolismHepatic
Elimination half-life2 to 3 hours
ExcretionRenal
Identifiers
  • N-Methyl-9,10-ethanoanthracene-9(10H)-methanamine
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H19N
Molar mass249.357 g·mol−1
3D model (JSmol)
  • c1ccc3c(c1)C4c2ccccc2C3(CC4)CNC
  • InChI=1S/C18H19N/c1-19-12-18-11-10-13(14-6-2-4-8-16(14)18)15-7-3-5-9-17(15)18/h2-9,13,19H,10-12H2,1H3 Y
  • Key:GNRXCIONJWKSEA-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Medically, benzoctamine is used as a treatment for anxious outpatients to control aggression, enuresis, fear, and minor social maladjustment in children. While it is a relatively new anti-anxiety drug, its popularity is increasing as a result of it being able to have comparable anxiolytic and sedative effects to other medications without their potentially fatal respiratory depressive side effects. Its anxiolytic effects are most similar to diazepam, another anxiolytic, but unlike diazepam, benzoctamine has antagonistic effects on epinephrine, norepinephrine, and appears to increase serotonin level. 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-octodienes. 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.

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