Benzquinamide
Basic information
- CAS
23844-24-8- Standard SMILES
CCN(CC)C(=O)C1CN2CCc3cc(OC)c(OC)cc3C2CC1OC(C)=O- InChIKey
JSZILQVIPPROJI-UHFFFAOYSA-N- Molecular formula
- C22H32N2O5
- Average molar mass
- 404.5 g/mol
- Monoisotopic mass
- 404.23112213
Overview
Benzquinamide is a monocarboxylic acid amide. It has a role as an antipsychotic agent, a sedative, a H1-receptor antagonist, a muscarinic antagonist and an antiemetic.
Names & identifiers
- Preferred name
- Benzquinamide
- IUPAC
- [3-(diethylcarbamoyl)-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizin-2-yl] acetate
- English name
- Benzquinamid
- Molecular formula
- C22H32N2O5
- Molecular weight
- 404.5
Names & synonyms
benzquinamidePromecon63-12-7Emete-conEmeticonBenzochinamideBenzoquinamideBenzquinamidumbenzquinamidaP-2647NSC-64375DTXSID9022657
Show more names
BZQBenzquinamidN,N-DIETHYL-1,3,4,6,7,11-BENZO(A)QUINOLIZINE-3-CARBOXAMIDE2H-Benzoaquinolizine-3-carboxamide, 2-(acetyloxy)-N,N-diethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-[3-(diethylcarbamoyl)-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-2-yl] acetate
2-Hydroxy-3-diethylcarbamyl-9,10-dimethoxy-1,2,3,4,6,7-hexahydro-11bH-benzoquinolizine acetate2H-Benzo(a)quinolizine-3-carboxamide, N,N-diethyl-1,3,4,6,7,11b-hexahydro-2-hydroxy-9,10-dimethoxy-, acetate (ester)NSC-108159NSC-1691932-Acetoxy-3-(N,N-diethylcarboxamido)-9,10-dimethoxy-1,2,3,4,6,7-hexahydro-11bH-benzopyridocoline2-Acetoxy-3-diethylcarbamyl-9,10-dimethoxy-1,2,3,4,6,7-hexahydro-11b-benzo(a)quinolizineDTXCID7026572-(Acetyloxy)-N,N-diethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzo(a)quinolizine-3-carboxamide
Database identifiers
- CAS
23844-24-8、63-12-7- PubChem CID
- 2342
- DTXSID
DTXSID9022657
Properties
Computed structural properties
- XLogP
- 2.1
- Topological polar surface area
- 68.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 7
- Heavy atoms
- 29
- Formal charge
- 0
- Complexity
- 582
Experimental & physicochemical properties
DrugsDEA NFLIS-Drug Category -> Depressants and Tranquilizers
LogP1.7
Color/FormCRYSTALS FROM DIISOPROPYL ETHER
Solubility4.90e-01 g/L
Human DrugsPharmaceuticals
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point
130-131.5
130-131.5 °C
131 °C
Physical DescriptionSolid
Stability/Shelf LifeSTABLE UP TO 5 YR @ 25 °C & UP TO 6% RELATIVE HUMIDITY; LIGHT-SENSITIVE; STABLE IN SOLN BETWEEN PH 2 & 4 /HCL/
Other Experimental PropertiesWHITE OR PALE YELLOW CRYSTALLINE POWDER; MP: 222-230 °C; DOES NOT EXHIBIT POLYMORPHISM; PKA 5.9; 1 G IS SOL IN ABOUT 12.5 ML WATER, 4 ML ALC, & 285 ML ACETONE /HCL/
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Regulatory Information
2H-Benzoaquinolizine-3-carboxamide, 2-(acetyloxy)-N,N-diethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Toxicology
Human Toxicity Excerpts
DROWSINESS APPEARS TO BE MOST COMMON ADVERSE EFFECT. OTHER ADVERSE REACTIONS... /INCL/ DRY MOUTH, SHIVERING, SWEATING, HICCOUGHS, FLUSHING, SALIVATION, & BLURRED VISION...HYPERTENSION, HYPOTENSION, DIZZINESS, ATRIAL FIBRILLATION, & PREMATURE AURICULAR & VENTRICULAR CONTRACTIONS...INSOMNIA, RESTLESSNESS, HEADACHE... /HCL/
...ADVERSE REACTIONS REPORTED ARE AS FOLLOWS: ...EXCITEMENT, NERVOUSNESS... ANOREXIA, NAUSEA...TWITCHING, SHAKING, TREMORS, & WEAKNESS...FATIGUE, CHILLS, INCR TEMP. /HCL/
Safety data
- Toxicity
- LD50 orally in rats: 990 mg/kg; i.p. in mice: 376 mg/kg (Goldenthal)
- Hazardous Substances Data
- 63-12-7(Hazardous Substances Data)
Chemistry & industry
Pharmacology
PharmacodynamicsBenzquinamide is an antiemetic compound with antihistaminic, mild anticholinergic, and sedative properties.
Mechanism of Action
The mechanism of action is not known, but presumably benzquinamide works via antagonism of muscarinic acetycholine receptors and histamine H1 receptors.
LIKE PHENOTHIAZINES, IT APPARENTLY INHIBITS STIMULI @ CHEMORECEPTOR TRIGGER ZONE. HOWEVER, IN CONTRAST...INCR CARDIAC OUTPUT, BLOOD PRESSURE, & RESP HAVE BEEN NOTED BOTH EXPTL & CLINICALLY WITH BENZQUINAMIDE. /HCL/
Biological Half-Life1-1.6 hours (for all formulations)
Metabolism/Metabolites
BENZQUINAMIDE YIELDS 2-ACETOXY-3-(N,N-DIETHYLCARBOXAMI DO)-1,2,3,4,6,7-HEXAHYDRO-9-HYDROXY-10-METHOXY-11BH-BENZOQUINOLIZINE & 2-ACETOXY-3-(N-ETHYLCARBOXAMIDO)-1,2,3,4,6,7-HEXAHYDRO- 9,10-DIMETHOXY-11BH-BENZOQUINOLIZINE IN MAN & DOG: WISEMAN, EH ET AL, BIOCHEM PHARMAC 13, 1421 (1964). /FROM TABLE/
BENZQUINAMIDE YIELDS 3-(N,N-DIETHYLCARBOXAMIDO)-1,2,3, 4,6,7-HEXAHYDRO-2-HYDROXY-9,10-DIMETHOXY-11BH-BENZOQUINOLIZINE IN MAN & DOG: WISEMAN, EH ET AL, BIOCHEM PHARMAC 13, 1421 (1964). /FROM TABLE/
Absorption, Distribution and ExcretionIncomplete, with 33–39% bioavailability via the capsule and suppository routes, relative to the intramuscular route.
Cellular LocationsMembrane
Uses & manufacturing
UsesMEDICATION
Methods of ManufacturingTRETTNER, US PATENT 3,053,845 (1962 TO PFIZER)
Formulations/PreparationsDOSAGE FORMS: INJECTION: 50 MG TO BE RECONSTITUTED WITH 2.2 ML STERILE WATER /HCL/
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Compound notes
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