Introduction：Basic information about Benoxinate Hydrochloride CAS 5987-82-6, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Benoxinate Hydrochloride Basic information
| Product Name: | Benoxinate Hydrochloride |
| Synonyms: | 2-(DIETHYLAMINO)ETHYL 4-AMINO-3-BUTOXYBENZOATE HYDROCHLORIDE;4-AMINO-3-BUTOXYBENZOIC ACID DIETHYLAMINOETHYL ESTER HYDROCHLORIDE;BENZOIC ACID, 4-AMINO-3-BUTOXY-, 2-(DIETHYLAMINO)ETHYL ESTER, MONOHYDROCHLORIDE;BENOXINATE HCL;BENOXINATE HYDROCHLORIDE;OXYBUPROCAINE HYDROCHLORIDE;cebesine;conjuncain |
| CAS: | 5987-82-6 |
| MF: | C17H29ClN2O3 |
| MW: | 344.88 |
| EINECS: | 227-808-8 |
| Product Categories: | AVIOCHINA |
| Mol File: | 5987-82-6.mol |
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Benoxinate Hydrochloride Chemical Properties
| Melting point | 157-160 C |
| storage temp. | 2-8°C |
| solubility | Very soluble in water, freely soluble in ethanol (96 per cent). |
| form | Solid |
| color | White to Off-White |
| Merck | 13,1045 |
| Major Application | pharmaceutical (small molecule) |
| InChI | InChI=1S/C17H28N2O3.ClH/c1-4-7-11-21-16-13-14(8-9-15(16)18)17(20)22-12-10-19(5-2)6-3;/h8-9,13H,4-7,10-12,18H2,1-3H3;1H |
| InChIKey | PRGUDWLMFLCODA-UHFFFAOYSA-N |
| SMILES | C1(C(=O)OCCN(CC)CC)=CC=C(N)C(OCCCC)=C1.Cl |
| CAS DataBase Reference | 5987-82-6(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi,Xn |
| Risk Statements | 36/37/38-20/21/22 |
| Safety Statements | 22-26-36 |
| RIDADR | UN 1544PSN2 6.1 / PGIII |
| WGK Germany | 3 |
| RTECS | DG1502900 |
| HS Code | 29225000 |
| Storage Class | 13 - Non Combustible Solids |
| Toxicity | LD50 scu-rat: 60 mg/kg NIIRDN 6,154,82 |
Benoxinate Hydrochloride Usage And Synthesis
| Chemical Properties | White or almost white, crystalline powder or colourless crystals. |
| Originator | Dorsacaine HCl,Dorsey,US,1953 |
| Uses | antibacterial, coccidiostat |
| Uses | Benoxinate Hydrochloride is a local anesthetic used in ophthalmology to numb the surface of the eye for a variety of procedures. |
| Uses | anticonvulsant |
| Definition | ChEBI: The monohydrochloride salt of oxybuprocaine. |
| Manufacturing Process | 25 grams of 3-oxy-4-nitrobenzoic acid are esterified (ethyl ester) and 26grams of the ester are dissolved in 200 cc of absolute ether and treated with7 grams of caustic potash in 20 cc of absolute methanol. The red potassiumphenolate with 7 grams of pure butyl bromide and 7 grams of absolute alcoholare heated for 5 hours in the oven to 150°C. When cool, the alcohol isevaporated in vacuo and the butoxy-nitrobenzoic acid ethyl ester isprecipitated with water. The substance is sucked off and saponified for 15minutes with a solution of 2.5 grams of caustic potash in 30 cc of alcohol on awater bath. The alcohol is evaporated in vacuo and the 3-butoxy-4-nitrobenzoic acid is precipitated with hydrochloric acid. It forms needles whichmelt at 174°C. 7.9 grams of dry acid are boiled for 45 minutes under a refluxcondenser with 25 cc of thionyl chloride. The excess of thionyl chloride is thenremoved in vacuo, and the oil is distilled. The acid chloride has a yellow colorand solidifies.
7.3 grams of the acid chloride are treated with 6.6 grams of diethyl-aminoethanolin 20 cc of absolute benzene. The mixture is then warmed for 1 houron a water bath. When cold, it is treated with a solution of soda and washedwith ether. After drying over potash, the ether and benzene are removed bydistillation and 3-butoxy-4-nitrobenzoic acid diethylamino-ethyl ester isobtained, having a BP 215°C/2.5 mm.
5.0 grams of this product are hydrogenated in absolute alcohol solution withfresh Raney nickel. When the absorption of hydrogen ceases (5 hours), thesolution is filtered and the alcohol evaporated in vacuo. The 3-butoxy-4-aminobenzoic acid diethyl-amino-ethyl ester boils at 215°-218°C at 2 mmpressure; it is an almost colorless oil.
By precipitation of a solution of the ester in absolute ether with hydrogenchloride gas, the dihydrochloride is obtained; upon recrystallization fromalcohol/ether, it forms crystals which melt at 196°-197°C. |
| Brand name | Dorsacaine (Novartis). |
| Therapeutic Function | Local anesthetic |
| Clinical Use | Benoxinate hydrochloride is a topical anesthetic. Benoxinate hydrochloride ophthalmic solution, 0.4%, was originally permitted in 1953 as Dorsacaine under NDA 08-729. The product was reviewed as part of the Drug Efficacy Study Implementation (DESI), found to be effective, approved and marketed by Dorsey until 1980. An abbreviated new drug application (ANDA) was also approved [Sola Barnes Hind (ANDA 84-149)] and marketed until 1991. |
| Side effects | The most common ocular adverse events associated with Benoxinate Hydrochloride when used as an eye drop ingredient (Fluorescein and Benoxinate Ophthalmic Solution) were: stinging, burning and conjunctival redness. Serious adverse reactions include corneal toxicity and corneal damage due to insensitivity. Other possible side effects include eye congestion, burning, stinging, eye irritation, blurred vision and punctate keratitis. |
| Safety Profile | Poison by subcutaneous route. A topical anesthetic. When heated to decomposition it emits toxic fumes of NOx and HCl. |
| structure and hydrogen bonding | Oxybuprocaine hydrochloride acts as a local anesthetic and is used in eye drop formulations. Mod. II, the stable polymorphic form, contains two molecules with markedly different conformations (stretched and bent). The 13C CPMAS NMR spectrum of this sample12 showed crystallographic splittings arising from the fact that there are two molecules in the asymmetric unit. An INADEQUATE two-dimensional experiment was used to link signals for the same independent molecule. Of the four ethyl groups attached to NHt nitrogens, one gives rise to unusually low chemical shifts, very different from those of the other three groups. This was attributed to gamma-gauche conformational effects, and confirmed by shielding computations. The oxybuprocaine system is too large for computations performed on the crystallographic unit and the intermolecular shielding effects have to be neglected. Nevertheless, the computed shifts do match the order of the experimental ones. The assignment of 13C signals to specific carbons in the two crystallographically inequivalent molecules of oxybuprocaine polymorph showed the power of NMR crystallography. |
Benoxinate Hydrochloride Preparation Products And Raw materials
| Raw materials | Sodium hydroxide-->Thionyl chloride-->1-Bromobutane-->4-Nitrobenzoic acid-->Diethylaminoethanol-->Ethyl benzoate-->Hydrogen-->Hydrochloric acid-->tert-Butanol-->Potassium hydroxide-->Ethanol |
