butyl 4-aminobenzoate
benzoic acid, 4-amino-, butyl ester
Identification
| Name | butyl 4-aminobenzoate |
| IUPAC | butyl 4-aminobenzoate |
| CAS Number | 94-25-7 |
| EINECS | 202-317-1 |
| FDA UNII | EFW857872Q |
| Molecular Formula | C11 H15 N O2 |
| Molecular Weight | 193.24595000 |
| MDL Number | MFCD00017112 |
| Nikkaji Number | J4.698A |
| Beilstein | 1211465 |
| XlogP3 | 2.90 (est) |
Regulatory
Physical Properties
| Appearance | yellw powder (est) |
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 58.00 °C. @ 760.00 mm Hg |
| Boiling Point | 325.68 °C. @ 760.00 mm Hg (est) |
| Flash Point | 364.00 °F. TCC ( 184.60 °C. ) (est) |
| logP (o/w) | 2.870 |
| Soluble in | water, 167.6 mg/L @ 25 °C (est) |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | not used anymore |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | intraperitoneal-mouse LD50 67 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | pharmaceuticals / chemical synthisis |
| Recommendation for butyl 4-aminobenzoate usage levels up to | not for fragrance use. |
| Recommendation for butyl 4-aminobenzoate flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
4-
amino-benzoic acid butyl ester
4-
aminobenzoic acid butyl ester
p-
aminobenzoic acid butyl ester
4-
aminobenzoic acid n-butyl ester
p-
aminobenzoic acid, butyl ester
benzoic acid, 4-amino-, butyl ester
benzoic acid, p-amino-, butyl ester
butamben
butesin
butoform
4-(
butoxycarbonyl)aniline
butyl p-aminobenzoate
N-
butyl p-aminobenzoate
butyl PABA
butyl-4-aminobenzoate
N-
butyl-p-aminobenzoate
butylcaine
planoform
scuroform
zyljectin
PubMed:
Modulation of peripheral Na(+) channels and neuronal firing by n-butyl-p-aminobenzoate.
PubMed:
The effect of oral topical anesthesia on the characteristics of voice.
PubMed:
Transdermal delivery of butamben using elastic and conventional liposomes.
PubMed:
Inhibition of sensory neuronal TRPs contributes to anti-nociception by butamben.
PubMed:
Butamben derivatives enhance BMP-2-stimulated commitment of C2C12 cells into osteoblasts with induction of voltage-gated potassium channel expression.
PubMed:
New "drug-in cyclodextrin-in deformable liposomes" formulations to improve the therapeutic efficacy of local anaesthetics.
PubMed:
On the bioreactivity of triorganotin aminobenzoates. Investigation of trialkyl and triarylyltin(IV) esters of 3-amino and 4-aminobenzoic acids.
PubMed:
The local anesthetic butamben inhibits total and L-type barium currents in PC12 cells.
PubMed:
The local anesthetic butamben inhibits and accelerates low-voltage activated T-type currents in small sensory neurons.
PubMed:
Structural characteristics and crystal polymorphism of three local anaesthetic bases crystal polymorphism of local anaesthetic drugs: part VII.
PubMed:
Inhibition of the A-type K+ channels of dorsal root ganglion neurons by the long-duration anesthetic butamben.
PubMed:
The block of total and N-type calcium conductance in mouse sensory neurons by the local anesthetic n-butyl-p-aminobenzoate.
PubMed:
Analgesic synergy between topical morphine and butamben in mice.
PubMed:
Antifolate chemistry: synthesis of 4-[N-[(6RS)-2-methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(prop-2-ynyl)amino]benzoic acid via a (propargyl)Co2(CO)6+ complex.
PubMed:
Analysis of a glucose tetrasaccharide elevated in Pompe disease by stable isotope dilution-electrospray ionization tandem mass spectrometry.
PubMed:
Purification and characterization of PrbA, a new esterase from Enterobacter cloacae hydrolyzing the esters of 4-hydroxybenzoic acid (parabens).
PubMed:
Kv1.1 channels of dorsal root ganglion neurons are inhibited by n-butyl-p-aminobenzoate, a promising anesthetic for the treatment of chronic pain.
PubMed:
Benzoate X receptors alpha and beta are pharmacologically distinct and do not function as xenobiotic receptors.
PubMed:
The antinociceptive and histologic effect of sciatic nerve blocks with 5% butamben suspension in rats.
PubMed:
Comparison of epidural butamben to celiac plexus neurolytic block for the treatment of the pain of pancreatic cancer.
PubMed:
Diffusion of n-butyl-p-aminobenzoate (BAB), lidocaine and bupivacaine through the human dura-arachnoid mater in vitro.
PubMed:
Orientations and locations of local anesthetics benzocaine and butamben in phospholipid membranes as studied by 2H NMR spectroscopy.
PubMed:
Identification of a yellow impurity in aged samples of aqueous butamben suspension: evidence for the oxidative degradation of poly(ethylene glycol).
PubMed:
Methemoglobinemia induced by topical anesthesia: a case report and review.
PubMed:
The long-term effect of epidural administration of butamben suspension on nerve injury-induced allodynia in rats.
PubMed:
Particle size determination of a flocculated suspension using a light-scattering particle size analyzer.
PubMed:
Nerve blocks with 5% butamben suspension for the treatment of chronic pain syndromes.
PubMed:
Partition coefficients (n-octanol/water) of N-butyl-p-aminobenzoate and other local anesthetics measured by reversed-phase high-performance liquid chromatography.
PubMed:
Epidural and intrathecal n-butyl-p-aminobenzoate solution in the rat. Comparison with bupivacaine.
PubMed:
The local anesthetic, n-butyl-p-aminobenzoate, reduces rat sensory neuron excitability by differential actions on fast and slow Na+ current components.
PubMed:
Characterization of site I on human serum albumin: concept about the structure of a drug binding site.
PubMed:
Analgesic efficacy of topical butamben picrate.
PubMed:
Capillary gas chromatographic method for the determination of n-butyl-p-aminobenzoate and lidocaine in plasma samples.
PubMed:
The local anesthetic n-butyl-p-aminobenzoate selectively affects inactivation of fast sodium currents in cultured rat sensory neurons.
PubMed:
Formulation factors affecting release of drug from topical vehicles. II. Effect of solubility on in vitro delivery of a series of n-alkyl p-aminobenzoates.
PubMed:
Long-lasting epidural sensory blockade by n-butyl-p-aminobenzoate in the terminally ill intractable cancer pain patient.
PubMed:
Preliminary study to assay plasma amethocaine concentrations after topical application of a new local anaesthetic cream containing amethocaine.
PubMed:
A 'forgotten' topical anaesthetic sensitizer: butyl aminobenzoate.
PubMed:
Butyl-p-aminobenzoate. Preparation, characterization and quality control of a suspension injection for epidural analgesia.
PubMed:
Long-lasting epidural sensory blockade by n-butyl p-aminobenzoate in the dog: neurotoxic or local anesthetic effect?
PubMed:
Effect of epidural and subarachnoid injections of a 10% butamben suspension.
PubMed:
Flocculation of suspensions containing nonionic surfactants by sorbitol.
PubMed:
Evaluation of anesthetic agents on human mucous membrane: an illustration of experimental protocol using computers.
PubMed:
[Clinical evaluation of new toothache drug "LTA"].
PubMed:
Topical anesthetics: use and misuse.
PubMed:
[Clinical investigation of the action of lidocaine, procaine and butanylcaine].
PubMed:
Methemoglobinemia induced by local anesthetics.
PubMed:
Controlled drug permeation. II. Comparative permeability and stability of butamben and benzocaine.
PubMed:
Controlled drug permeation I: controlled release of butamben through silicone membrane by complexation.
PubMed:
Specificity of eczematous hypersensitivity to p-aminobenzoic acid butyl ester (butesin).