Butyl-4-aminobenzoat
Butyl 4-aminobenzoate
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Grundinformationen
- CAS
94-25-7- Standard-SMILES
CCCCOC(=O)c1ccc(N)cc1- InChIKey
IUWVALYLNVXWKX-UHFFFAOYSA-N- Summenformel
- C11H15NO2
- Durchschnittliche Molmasse
- 193,24 g/mol
- Monoisotopische Masse
- 193,11027872
Überblick
N-butyl-p-aminobenzoate is a yellow powder. Insoluble in water. (NTP, 1992)
Namen und Bezeichner
- Bevorzugter Name
- Butyl 4-aminobenzoate
- IUPAC
- butyl 4-aminobenzoate
- Lokaler Name
- Butyl-4-aminobenzoat
- Englischer Name
- Butyl 4-aminobenzoate
- Summenformel
- C11H15NO2
- Molmasse
- 193.24
Namen und Synonyme
Butyl 4-aminobenzoatebutamben94-25-7ButesineButoformButyl aminobenzoateButylcainePlanoformScuroformScuroforme4-(Butoxycarbonyl)anilineButyl keloform
Weitere Namen anzeigen
butylaminobenzoateButesinButseinBUTOFORMEBUTAMBERO
Benzoic acid, 4-amino-, butyl esterN-Butyl p-aminobenzoatep-Aminobenzoic acid butyl ester4-Aminobenzoic acid butyl esterButyl PABADTXSID7022417NSC-128464EFW857872Q
Datenbank-Bezeichner
- CAS
94-25-7- PubChem CID
- 2482
- DTXSID
DTXSID7022417- ChEMBL
CHEMBL127516- ChEBI
CHEBI:3231- UNII
- EFW857872Q
- EC Number
- 202-317-1
- Nikkaji
- J4.698A
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- 2,9
- Polarare Oberfläche (TPSA)
- 52,3 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 5
- Schwere Atome
- 14
- Formalladung
- 0
- Komplexität
- 174
Experimentelle und physikochemische Eigenschaften
Chemical ClassesOther Uses -> Sunscreens
DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesFusion temperature
LogP
log Kow= 2.87
3.05
OdorOdorless
TasteTasteless
Color/Form
Crystals from alc
White powder
White, amorphous powder
Solubility
Insoluble (NTP, 1992)
1 g dissolves in about 7 liters water
Sol in dil acids, alc, chloroform, ether, and fatty oils.
Soluble in dilute acids, alcohol, chloroform, ether, and fatty oils.
Soluble in thanol, ethyl ether, and benzene.
Endocrine DisruptorsPotential endocrine disrupting compound
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 43 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory InformationBenzoic acid, 4-amino-, butyl ester: 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.
Other Safety InformationIMAP assessments - Benzoic acid, 4-amino-, butyl ester: Human health tier I assessment
Fire HazardsFlash point data for this chemical are not available. It is probably combustible. (NTP, 1992)
Fire PotentialCombustible when exposed to heat or flame.
Health HazardsSYMPTOMS: Symptoms of exposure to this compound may include sensitivity dermatitis, nausea, vomiting and methemoglobinemia.
Hazards SummaryMay cause tissue necrosis after injection, possible due to precipitation of crystals; [HSDB] May cause methemoglobinemia and skin sensitization; [CAMEO] An irritant; May cause skin sensitization; [MSDSonline]
FDA Requirements
Chemie und Industrie
Pharmakologische Informationen
Protein BindingAs all other local anesthetics, it is thought that butamben will be highly bound to plasma proteins, mainly to alpha-1-acid glycoprotein.
Pharmacodynamics
Butamben has been shown to selectively inhibit dorsal root pain signal transmission for periods of months when administered as epidural suspensions. The effect of butamben is not related to any significant loss of motor function which indicates that it targets specifically the pain-sensing C fibers of the dorsal root. When administered topically, butamben produced anesthesia by accumulating in the nerve cell membrane causing it to expand and lose its ability to depolarize and blocking the impulse transmission.
Mechanism of Action
Butamben acts by inhibiting the voltage-gated calcium channels in dorsal root ganglion neurons. The modification in this channels is thought to cause a disturbance of the channel kinetics acceleration. It is reported as well that butamben is an inhibitor of the sodium channels and a delayed rectifier of potassium currents. All the effects of butamben are performed in the root ganglion neurons which suggests that the related anesthetic effect may be caused by the reduced electrical excitability.
...ACTION IS TO INTERFERE WITH INITIATION & TRANSMISSION OF NERVE IMPULSE. PRESENT THEORY HOLDS THAT LOCAL ANESTHETICS PREVENT DEPOLARIZATION OF NERVE MEMBRANE &, HENCE, PROPAGATION OF IMPULSE. ...THOUGHT TO BE DUE TO INTERFERENCE WITH MUTUAL EXCHANGE OF SODIUM & POTASSIUM IONS ACROSS MEMBRANE. /LOCAL ANESTHETICS/
Biological Half-LifeThe effective half-life of unencapsulated butamben is registered to be of 90 minutes. Some efforts were made to prepare D, L-lactic acid capsules which increased the half-life of butamben to even 400 hours.
Metabolism/MetabolitesThe metabolic pathway of butamben follows the same pattern of other local anesthetics and it is driven mainly by the hydrolysis via cholinesterase for the formation of inert metabolites.
MeSH Pharmacological Classification
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