359-83-1

Usage

Uses

Used in Pharmaceutical Industry:
PENTAZOCINE is used as an analgesic (narcotic) for the management of moderate to severe pain. It exhibits mixed agonist-antagonist activity at the opioid receptor subtypes, with partial agonist and weak antagonist properties at the κ-receptor. This unique profile contributes to its effectiveness in pain relief while potentially reducing the risk of dependence and addiction compared to other opioids.
Used in Research Applications:
PENTAZOCINE is utilized in research settings to study the effects and mechanisms of action of opioid receptors, as well as to develop new drugs with improved safety and efficacy profiles. Its interaction with the σ-receptor also makes it a valuable tool for investigating the role of this receptor in various physiological and pathological processes.
Used in Forensic Applications:
As a controlled substance, PENTAZOCINE is employed in forensic science for the detection and analysis of drug abuse, particularly in cases involving the misuse of prescription opioids. Its unique pharmacological properties and potential for abuse make it a relevant target for forensic investigations.
Brand Names:
PENTAZOCINE is available under various brand names, including Talwin (Sanofi Aventis), Fortagesic, Fortalgesic, Fortralin, Fortwin, Pentafen, Pentalgina, Talacen, and Talwin NX. Talwin NX, in particular, combines PENTAZOCINE with a low dose of the antagonist naloxone (0.5 mg) to discourage intravenous drug abuse.

Originator

Pentazocine,Mallinckrodt Inc.

Manufacturing Process

A solution of 3,4-dimethylpyridine was added to a methyliodid. Then to the resulting solution containing 1,3,4-trimethylpyridinium iodide the 4methoxybenzylmagnesium chloride was added. After reaction process the 1,3,4-trimethyl-2-(4-methoxy-benzyl)-pyridine was obtained.To the solution of 1,3,4-trimethyl-2-(4-methoxy-benzyl)-pyridine was reduced by hydrogen over 10% palladium-on-charcoal, and when reduction was complete, the catalyst was removed by filtration and the filtrate taken to dryness. The residue was recrystallized to give 2-(4-methoxybenzyl)-1,3,4trimethyl-1,2,5,6-tetrahydropyridine.To the 2-(4-methoxybenzyl)-1,3,4-trimethyl-1,2,5,6-tetrahydropyridine the solution of hydrobromic acid was added and heated under reflux.The product obtained was recrystallized and yield N-methyl-1,2,3,4,5,6-hexahydro-6,11dimethyl-8-hydroxy-2,6-methano-3-benzazocine (2'-hydroxy-2,5,9trimethylbenzo-6-morphen), which then was demethylated by bromcyan (BrCN). As a result the racemic cis-1,2,3,4,5,6-hexahydro-6,11-dimethyl-8hydroxy-2,6-methano-3-benzazocine was obtained (that is a. 2'-hydroxy-5,9dimethyl-6,7-benzomorphen).A mixture of 8.7 g racemic cis-1,2,3,4,5,6-hexahydro-6,11-dimethyl-8hydroxy-2,6-methano-3-benzazocine, 6.0 g of 1-bromo-3-methyl-2-butene, 5.0 g of sodium bicarbonate, and 125 ml of N,N-dimethylformamide was stirred and refluxed for approximately 4.5 hours. The reaction mixture was then filtered, and the solid on the filter was washed with ethanol. The filtrate and the wash liquor were combined, concentrated under reduced pressure, and then extracted with chloroform. The chloroform extract was concentrated under reduced pressure to yield a syrup which weighed 15.8 g. This syrup was dissolved in 120 ml of diethyl ether and the resulting solution was filtered to remove approximately 0.5 g of a brown amorphous solid. The filtrate was extracted with a mixture of 5 ml of concentrated hydrochloric acid and 20 ml of water. To the extract there was added 5 ml of concentrated ammonium hydroxide solution and ice. A pale tan syrup separated from solution and after stirring, this syrup solidified. The resulting pale tan solid was collected and dried; it weighed 10.6 g. After two recrystallizations from a mixture of methyl alcohol and water, with charcoaling, the 1,2,3,4,5,6-hexahydro-3-(3-methyl-2butenyl)-6,11-dimethyl-8-hydroxy-2,6-methano-3-benzazocine weighed 8.2 g and melted at 145°-147°C.The1,2,3,4,5,6-hexahydro-3-(3-methyl-2-butenyl)-6,11-dimethyl-8-hydroxy2,6-methano-3-benzazocinewas soluble in a mixture of 0.35 ml of 2 N hydrochloric acid and 0.15 ml of water to the extent of 10%, the pH of the 1% solution being 2.80; and when the pH of the 1% solution was gradually raised by addition of 10 N sodium hydroxide solution, a precipitate formed at pH 5.4. The 1,2,3,4,5,6-hexahydro-3-(3-methyl-2-butenyl)-6,11-dimethyl-8hydroxy-2,6-methano-3-benzazocine hydrochloride melted at 245°-247°C, dec.

Therapeutic Function

Analgesic

World Health Organization (WHO)

Pentazocine, which has both agonist and weak opioid antagonist activity, was introduced in 1967 for the treatment of moderate and severe pain. The risk of drug dependence is lower with pentazocine than with morphine-like drugs and pentazocine has been controlled under Section III of the 1971 Convention on Psychotropic Substances since 1984. The risk of dependence is now widely acknowledged to exist in vulnerable individuals and at least one country has applied controls analogous to those of Schedule I of the 1961 Single Convention on Narcotic Drugs. (Reference: (UNCPS3) United Nations Convention on Psychotropic Substances (III), , , 1971)

Safety Profile

Poison by ingestion, subcutaneous, intramuscular, intraperitoneal, and intravenous routes. Experimental reproductive effects. Human systemic effects by intramuscular and intravenous routes: wakefulness, euphoria, hallucinations or distorted perceptions, tremors, convulsions, excitement, motor activity changes, muscle weakness, analgesia, withdrawal, parasympathomimetic effects, nausea or vomiting, and dernlititis. Can cause drug dependency and other central nervous system effects, An analgesic. When heated to decomposition it emits toxic fumes of NOx. See also ALLIT COMPOUNDS.

InChI:InChI=1/C19H27NO/c1-13(2)7-9-20-10-8-19(4)14(3)18(20)11-15-5-6-16(21)12-17(15)19/h5-7,12,14,18,21H,8-11H2,1-4H3/t14-,18+,19+/m0/s1

Upstream product

• 16603-67-1 (-)-cis-N-Normetazocine 
• 870-63-3 prenyl bromide 
• 5703-26-4 4-Methoxyphenylacetaldehyde 
• 1033702-80-5 C₂₁H₂₅NO 
• 90667-54-2 N-(3-methyl-3-pentenyl)phthalimide 
• 57253-31-3 (E)-5-bromo-3-methylpentyl-2-ene 
• 18175-34-3 2-(4-methoxy-benzyl)-3,4-dimethyl-piperidin-4-ol 
• 123-11-5 4-methoxy-benzaldehyde 
• 16603-67-1 (2R,6R,11R)-6,11-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-ol 
• 42245-42-1 methyl 3-(4-methoxyphenyl)glycidate 
• 577991-77-6 [2-((R)-7-Methoxy-1-methyl-2-methylene-1,2,3,4-tetrahydro-naphthalen-1-yl)-ethyl]-(3-methyl-but-2-enyl)-amine 
• 577991-79-8 3-((R)-7-Methoxy-1-methyl-2-methylene-1,2,3,4-tetrahydro-naphthalen-1-yl)-propane-1,2-diol 

Downstream Products

• 71780-69-3 Thiobenzoic acid S-[(6R,11R)-6,11-dimethyl-3-(3-methyl-but-2-enyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-yl] ester 
• 83434-64-4 Thiobenzoic acid S-[(2R,6R,11R)-6,11-dimethyl-3-(3-methyl-but-2-enyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-yl] ester 

Relevant academic research and scientific papers

Pentazocine prodrug as well as preparation method and application thereof

The invention discloses a pentazocine prodrug shown as a formula (I), a preparation method thereof and medical application of a pharmaceutical preparation containing the pentazocine prodrug, wherein Ris hydrogen or deuterium. The water solubility of the prodrug compound is improved by 20 times or above at room temperature, the prodrug compound is chemically stable, the onset time is delayed, thedrug effect is prolonged, meanwhile, the same parent drug blood concentration is generated at a low dosage, and the prodrug compound has a wide clinical application prospect.

Asymmetric syntheses of (-)-pentazocine and (-)-eptazocine through an aza-prins cyclization

Two down more to go: The asymmetric syntheses of (-)-pentazocine and (-)-eptazocine are presented. The highlights of the syntheses are the construction of the core skeleton through an aza-Prins cyclization and intramolecular Friedel-Crafts reaction. Copyr

Enantiocontrolled synthesis of (-)-9-epi-pentazocine and (-)-aphanorphine

(Chemical Equation Presented) We have developed novel asymmetric routes to (-)-9-epi-pentazocine and (-)-aphanorphine from a D-tyrosine derivative. The tricyclic frameworks of (-)-9-epi-pentazocine and (-)-aphanorphine were assembled stereoselectively via intramolecular Friedel-Crafts reaction of the corresponding bicyclic precursors, generated with titanium-promoted enyne cyclization and indium-initiated atom-transfer radical cyclization, respectively.

Combination of selected opioids with muscarine antagonists for treating urinary incontinence

Active compound combinations of compounds of group A, particularly opioids, and compounds of group B, particularly anti-muscarine agents and other substances suitable for treatment of an increased urge to urinate or urinary incontinence. Related pharmaceutical formulations and methods of treatment of an increased urge to urinate or urinary incontinence are also provided.

Migratory hydroamination: A facile enantioselective synthesis of benzomorphans

We describe a highly efficient, general strategy for the enantioselective synthesis of benzomorphans (45-46% overall yield from commercially available material). The new synthesis demonstrates the effectiveness of an unprecedented diastereoselective cycloisomerization via migratory hydroamination and the power of palladium-catalyzed asymmetric allylic alkylation (AAA) of simple ketone enolates in the context of complex synthesis. The strategy outlined here for the enantioselective synthesis of three contiguous stereogenic centers and the novel cycloisomerization should have many applications in alkaloid synthesis. Copyright

Analgesic 3-(3-methyl-3-butenyl)-1,2,3,4,5,6-hexahydro-6,11-dimethyl-8-hydroxy-2,6-methano-3-benzazocine

Disclosed is 3-(3-methyl-3-butenyl)-1, 2, 3, 4, 5, 6-hexahydro-6, 11-dimethyl-8-hydroxy-2, 6-methano-3-benzazocine, a new derivative of benzazocine, which has superior analgesic properties.