Identification

Generic Name
Benzoctamine
DrugBank Accession Number
DB09021
Background

Benzoctamine is a drug with two main uses. It can be used as a sedative which does not depress the respiratory system, but rather stimulates it. It can also be used as an anxiolytic with the same efficacy as chlordiazepoxide for treating anxiety neurosis.

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 249.357
Monoisotopic: 249.151749616
Chemical Formula
C18H19N
Synonyms
  • Benzoctamine
  • N-Methyl-9,10-ethanoanthracene-9(10H)-methanamine

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Benzoctamine acts as a sedative and axiolytic agent 2,3.

Mechanism of action

The exact mechanism by which bezoctamine reduces anxiety and produces sedation is unknown. It has been found to increase serotonin levels in the forebrain which may mediate anxiolytic effects similar to those of serotonin selective reuptake inhibitors 1.

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Benzoctamine is combined with 1,2-Benzodiazepine.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Benzoctamine.
AcetophenazineThe risk or severity of adverse effects can be increased when Acetophenazine is combined with Benzoctamine.
AclidiniumBenzoctamine may increase the central nervous system depressant (CNS depressant) activities of Aclidinium.
AgomelatineThe risk or severity of adverse effects can be increased when Agomelatine is combined with Benzoctamine.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Benzoctamine.
AlimemazineThe risk or severity of adverse effects can be increased when Alimemazine is combined with Benzoctamine.
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with Benzoctamine.
AlosetronThe risk or severity of adverse effects can be increased when Alosetron is combined with Benzoctamine.
AlprazolamThe risk or severity of adverse effects can be increased when Alprazolam is combined with Benzoctamine.
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Benzoctamine hydrochloride1C280S920Q10085-81-1NZPJYSIIKYJREH-UHFFFAOYSA-N
International/Other Brands
Tacitin (Ciba-Geigy)

Categories

ATC Codes
N05BD01 — Benzoctamine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as anthracenes. These are organic compounds containing a system of three linearly fused benzene rings.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Anthracenes
Sub Class
Not Available
Direct Parent
Anthracenes
Alternative Parents
Tetralins / Aralkylamines / Dialkylamines / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Amine / Anthracene / Aralkylamine / Aromatic homopolycyclic compound / Hydrocarbon derivative / Organic nitrogen compound / Organonitrogen compound / Organopnictogen compound / Secondary aliphatic amine / Secondary amine
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
734MM7Y191
CAS number
17243-39-9
InChI Key
GNRXCIONJWKSEA-UHFFFAOYSA-N
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
IUPAC Name
methyl({tetracyclo[6.6.2.0²,⁷.0⁹,¹⁴]hexadeca-2,4,6,9,11,13-hexaen-1-yl}methyl)amine
SMILES
CNCC12CCC(C3=CC=CC=C13)C1=CC=CC=C21

References

Synthesis Reference

U.S. Patent 3,399,201.

General References
  1. Lippmann W, Pugsley TA: Effects of benzoctamine and chlordiazepoxide on turnover and uptake of 5-hydroxytryptamine in the brain. Br J Pharmacol. 1974 Aug;51(4):571-5. [Article]
  2. Authors unspecified: Tacitin and nobrium: new drugs for anxiety. Drug Ther Bull. 1971 Nov 19;9(24):93-4. [Article]
  3. Goodwin NM, Brock-Utne JG, Downing JW, Coleman AJ: Benzoctamine. A preliminary report on a new sedative drug. Anaesthesia. 1974 Nov;29(6):715-20. [Article]
KEGG Drug
D03089
PubChem Compound
28425
PubChem Substance
347827818
ChemSpider
26444
ChEBI
135017
ChEMBL
CHEMBL2110603
ZINC
ZINC000001481983
Wikipedia
Benzoctamine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US3399201No1966-04-121986-04-12US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)320-322U.S. Patent 3,399,201.
Predicted Properties
PropertyValueSource
Water Solubility0.000844 mg/mLALOGPS
logP4.16ALOGPS
logP3.64Chemaxon
logS-5.5ALOGPS
pKa (Strongest Basic)10.04Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count1Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area12.03 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity89.95 m3·mol-1Chemaxon
Polarizability29.31 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Drug created at June 24, 2014 20:36 / Updated at January 02, 2022 12:00