Explore a selection of our essential drug information below, or:
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
Structure for Benzoctamine (DB09021)
- 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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- 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Benzoctamine is combined with 1,2-Benzodiazepine. Acetazolamide The risk or severity of CNS depression can be increased when Acetazolamide is combined with Benzoctamine. Acetophenazine The risk or severity of CNS depression can be increased when Acetophenazine is combined with Benzoctamine. Agomelatine The risk or severity of CNS depression can be increased when Agomelatine is combined with Benzoctamine. Alfentanil The risk or severity of CNS depression can be increased when Alfentanil is combined with Benzoctamine. - Food Interactions
- Not Available
Products
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Ingredient UNII CAS InChI Key Benzoctamine hydrochloride 1C280S920Q 10085-81-1 NZPJYSIIKYJREH-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
- 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]
- Authors unspecified: Tacitin and nobrium: new drugs for anxiety. Drug Ther Bull. 1971 Nov 19;9(24):93-4. [Article]
- 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]
- External Links
- KEGG Drug
- D03089
- PubChem Compound
- 28425
- PubChem Substance
- 347827818
- ChemSpider
- 26444
- ChEBI
- 135017
- ChEMBL
- CHEMBL2110603
- ZINC
- ZINC000001481983
- Wikipedia
- Benzoctamine
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US3399201 No 1966-04-12 1986-04-12 US 
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 320-322 U.S. Patent 3,399,201. - Predicted Properties
Property Value Source Water Solubility 0.000844 mg/mL ALOGPS logP 4.16 ALOGPS logP 3.64 Chemaxon logS -5.5 ALOGPS pKa (Strongest Basic) 10.04 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 12.03 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 89.95 m3·mol-1 Chemaxon Polarizability 29.31 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0006-9040000000-8d5099f5515a57a2b586 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0udi-0090000000-9f940a1a3aafe7ee8906 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-0090000000-3f77e2f2218f05f76583 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-0090000000-efccc86dfda599fb46a9 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-0090000000-9d619c839ece72145bac Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-066r-0090000000-5b87595b3d8eb4178293 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-3090000000-b5bb9669343160554563 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 164.2085444 predictedDarkChem Lite v0.1.0 [M-H]- 155.67807 predictedDeepCCS 1.0 (2019) [M+H]+ 165.5156444 predictedDarkChem Lite v0.1.0 [M+H]+ 158.03609 predictedDeepCCS 1.0 (2019) [M+Na]+ 164.3678444 predictedDarkChem Lite v0.1.0 [M+Na]+ 164.12935 predictedDeepCCS 1.0 (2019)
Drug created at June 24, 2014 20:36 / Updated at October 14, 2024 10:05