Benzoctamine

Benzoctamine

Clinical data
Trade names	Tacitin
Routes of administration	Oral, intravenous
ATC code	N05BD01 (WHO)
Legal status
Legal status	BR: Class C1 (Other controlled substances)[1] In general: legal
Pharmacokinetic data
Bioavailability	100% for intravenous, 90% for oral
Metabolism	Hepatic
Elimination half-life	2 to 3 hours
Excretion	Renal
Identifiers
IUPAC name N-Methyl-9,10-ethanoanthracene-9(10H)-methanamine
CAS Number	17243-39-9 N
PubChem CID	28425
DrugBank	DB09021 N
ChemSpider	26444 Y
UNII	734MM7Y191
ChEMBL	ChEMBL2104106 N
CompTox Dashboard (EPA)	DTXSID4022654
Chemical and physical data
Formula	C18H19N
Molar mass	249.357 g·mol−1
3D model (JSmol)	Interactive image
SMILES c1ccc3c(c1)C4c2ccccc2C3(CC4)CNC
InChI 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)

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,^[2] enuresis,^[3] fear, and minor social maladjustment in children.^[2] re 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.