127-35-5 Usage
Description
Phenazocine is an opioid analgesic drug that is closely related to Pentazocine. It is known for its potent analgesic effects, being approximately four times more potent than morphine. Phenazocine is used to provide relief from pain, particularly in cases of biliary or pancreatic pain, and is associated with a lower incidence of side effects compared to other opioids. It acts on κ-opioid and σ receptors, which can also lead to feelings of euphoria and, in some cases, dysphoria and hallucinations at high doses. Due to its potential for misuse, Phenazocine is classified as a controlled substance.
Uses
Used in Pain Management:
Phenazocine is used as an analgesic agent for the treatment of moderate to severe pain. Its high potency and relatively low side effects make it a preferred choice for managing pain, particularly in cases of biliary or pancreatic pain.
Used in Pharmaceutical Industry:
Phenazocine is used as an active pharmaceutical ingredient in the development of pain relief medications. Its potent analgesic properties and lower side effect profile contribute to its use in the formulation of various pharmaceutical products.
Controlled Substance:
Phenazocine is classified as a controlled substance due to its potential for misuse and addiction. This classification helps regulate its distribution, prescription, and use, ensuring that it is only available to patients who genuinely need it for medical purposes.
Brand Name:
Phenazocine is marketed under the brand name Prinadol by SmithKline Beecham, a pharmaceutical company. This brand name is associated with the drug's use in pain management and its classification as a controlled substance.
Originator
Phenazocine, SmithKline French (GSK)
Manufacturing Process
25.0 g 3,4-lutidine methyl iodide in 60 ml of dry ethyl ether is stirred while 400 ml of a 0.3958 N ethereal solution of p-methoxybenzylmagnesium chloride is added at room temperature. The mixture is stirred for 30 minutes and then decomposed with a solution of 100 ml of water containing 25 g of ammonium chloride and 10 ml of concentrated ammonium hydroxide. The layers are separated. The organic layer is extracted with a solution of 75 ml of water and 17 ml of concentrated hydrochloric acid. The extracts are neutralized and taken into ether. The volatiles are evaporated to leave a light yellow oil, the dehydro base.The oily residue is then hydrogenated at 17 p.s.i. of hydrogen with 5% palladium-on-barium sulfate in 100 ml of 2 N hydrochloric acid for six hours. The reaction mixture is filtered, made alkaline and taken through ether to give the tetrahydro base as a clear oil.The oily tetrahydro base (about 10.0 g) in 150 ml of 48% hydrobromic acid is heated at 135°C for 24 hours, and then quenched in an ice Treating with baseand taking through chloroform gives a brown residue of the isomeric mixture of 2'-hydroxy-2,5,9-trimethyl-6,7-benzmorphan.This residue is triturated with ether, cooled and the resulting slurry filtered. The solid product is dissolved in a minimum of dry ethanol and made acid with ethereal hydrogen chloride. The cooled mixture is filtered to give the hydrochloride salt of the N-methyl-iso-benzmorphan, MP: 279-282°C, after recrystallization from ethanol. The base melts at 215°C.The ethereal filtrate is evaporated. A residue is neutralized to give the crude normal N-methyl-benzmorphan isomer, MP: 229-230°C. The hydrochloride salt of this isomer is formed, MP: 196-198°C, as a hydrate. A mixture of 10.0 g of the N-methyl-iso-benzmorphan isolated above in 15 ml of acetic anhydride is heated on the steam bath for about an hour, then quenched in an ice slurry. The mixture is then neutraliized and taken through ether to give the O-acetate derivative, iso-2'-acetoxy-2,5,9-trimethyl-6,7-benzomorphan. The crude acetate (9.5 g) is reacted with 5.0 g of cyanogen bromide in 100 ml of chloroform at reflux for several hours. The volatiles are removed in vacuo to leave a residue, which is refluxed in 150 ml of dilute hydrochloric acid for 24 hours. The mixture is cooled, neutralized and taken through chloroform to give the desired base with two methyl groups as a viscous syrup which crystallized slowly, MP: 173-175°C from methanol. The base, 6.5 g, is reacted with 5.0 g of phenylacetyl chloride in the presence of an excess of sodium carbonate in water. The mixture is stirred for several hours, diluted with water and taken into ether to give the N-phenacetylated compound. This compound in ether (250 ml) is reacted with an excess of 1.5 M ethereal lithium aluminum hydride at reflux overnight. The reaction mixture is evaporated to dryness, after quenching carefully with water and hydrobromic acid, to give the crude 2'-hydroxy-5,9-dimethyl-2-phenethyl-6,7-benzomorphan hydrobromide salt which is optionally recrystallized from ethanol, MP: 272273°C. The hydrobromide salt in the normal series melts at 170-173°C. The base is isolated by neutralizing of the hydrobromide salt in an ether alkali mixture, with following separating and evaporating the organic solvent.
Therapeutic Function
Narcotic analgesic
Check Digit Verification of cas no
The CAS Registry Mumber 127-35-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 7 respectively; the second part has 2 digits, 3 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 127-35:
(5*1)+(4*2)+(3*7)+(2*3)+(1*5)=45
45 % 10 = 5
So 127-35-5 is a valid CAS Registry Number.
InChI:InChI=1/C22H27NO/c1-16-21-14-18-8-9-19(24)15-20(18)22(16,2)11-13-23(21)12-10-17-6-4-3-5-7-17/h3-9,15-16,21,24H,10-14H2,1-2H3/t16-,21+,22+/m0/s1
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