Benzoctamine

Identification

Name
Benzoctamine
Accession Number
DB09021
Type
Small Molecule
Groups
Experimental
Description

Benzoctamine is a drug that possesses sedative and anxiolytic properties. It is different from most sedative drugs because in most clinical trials it does not produce respiratory depression, but actually stimulates the respiratory system. Benzoctamine has been found to have the same efficacy as chlordiazepoxide when treating anxiety neurosis.

Structure
Thumb
Synonyms
  • N-Methyl-9,10-ethanoanthracene-9(10H)-methanamine
Product Ingredients
IngredientUNIICASInChI Key
Benzoctamine hydrochloride1C280S920Q10085-81-1NZPJYSIIKYJREH-UHFFFAOYSA-N
International/Other Brands
Tacitin (Ciba-Geigy)
Categories
UNII
734MM7Y191
CAS number
17243-39-9
Weight
Average: 249.357
Monoisotopic: 249.151749616
Chemical Formula
C18H19N
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

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Benzoctamine is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when 3,4-Methylenedioxyamphetamine is combined with Benzoctamine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Benzoctamine.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Benzoctamine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Benzoctamine is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when 7-Nitroindazole is combined with Benzoctamine.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline is combined with Benzoctamine.
AcepromazineThe risk or severity of adverse effects can be increased when Acepromazine is combined with Benzoctamine.
AceprometazineThe risk or severity of adverse effects can be increased when Aceprometazine is combined with Benzoctamine.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Benzoctamine.
Food Interactions
Not Available

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. [PubMed:4480288]
  2. Authors unspecified: Tacitin and nobrium: new drugs for anxiety. Drug Ther Bull. 1971 Nov 19;9(24):93-4. [PubMed:4945942]
  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. [PubMed:4479725]
External Links
KEGG Drug
D03089
PubChem Compound
28425
PubChem Substance
347827818
ChemSpider
26444
ChEBI
135017
ChEMBL
CHEMBL2110603
Wikipedia
Benzoctamine
ATC Codes
N05BD01 — Benzoctamine

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US3399201No1966-04-121986-04-12Us

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

Taxonomy

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
Anthracene / Tetralin / Aralkylamine / Secondary amine / Secondary aliphatic amine / Organic nitrogen compound / Organopnictogen compound / Hydrocarbon derivative / Organonitrogen compound / Amine
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
Not Available

Drug created on June 24, 2014 14:36 / Updated on November 02, 2018 08:46