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PENTAZOCINE

Product Name
PENTAZOCINE
CAS No.
359-83-1
Chemical Name
PENTAZOCINE
Synonyms
Lexir;C07421;II-C-2;Talwan;Talwin;Fortral;KF-1820;Liticon;nih7958;sosegon
CBNumber
CB1121418
Molecular Formula
C19H27NO
Formula Weight
285.43
MOL File
359-83-1.mol
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PENTAZOCINE Property

Melting point:
145.4-147.20C
Boiling point:
427.85°C (rough estimate)
Density 
1.0104 (rough estimate)
refractive index 
1.5180 (estimate)
Flash point:
9℃
storage temp. 
Controlled Substance, -20°C Freezer
solubility 
DMSO: >10mg/mL
pka
pKa 8.68±0.05;11.23± 0.05(H2O,t =20,I=0.1) (Uncertain)
form 
solid
color 
white
CAS DataBase Reference
359-83-1
EPA Substance Registry System
2,6-Methano-3-benzazocin-8-ol, 1,2,3,4,5,6-hexahydro-6,11-dimethyl-3-(3-methyl-2-buten-1-yl)-, (2R,6R,11R)-rel- (359-83-1)
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Safety

Hazard Codes 
Xn,T,F
Risk Statements 
22-39/23/24/25-23/24/25-11
Safety Statements 
7-16-36/37-45
RIDADR 
UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany 
3
RTECS 
PB8750000
HS Code 
2933330000
Hazardous Substances Data
359-83-1(Hazardous Substances Data)
Toxicity
LD50 s.c. in male rats: 175±36 mg/kg (Goldenthal)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
P-073
Product name
Pentazocine solution
Purity
1.0?mg/mL in methanol, ampule of 1?mL, certified reference material, Cerilliant?
Packaging
1mL
Price
$26.6
Updated
2024/03/01
Sigma-Aldrich
Product number
1505007
Product name
(?)-Pentazocine
Packaging
500mg
Price
$522
Updated
2024/03/01
Cayman Chemical
Product number
15912
Product name
(-)-Pentazocine
Purity
≥98%
Packaging
1mg
Price
$35
Updated
2021/12/16
Cayman Chemical
Product number
15912
Product name
(-)-Pentazocine
Purity
≥98%
Packaging
5mg
Price
$158
Updated
2021/12/16
Sigma-Aldrich
Product number
P134
Product name
(?)-Pentazocine
Purity
≥98% (HPLC)
Packaging
50mg
Price
$767
Updated
2024/03/01
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PENTAZOCINE Chemical Properties,Usage,Production

Chemical Properties

Crystalline Solid

Originator

Pentazocine,Mallinckrodt Inc.

Uses

Mixed opioid agonist-antagonist. Controlled substance. Analgesic (narcotic).

Uses

(?)-Pentazocine is a benzomorphan-type opiate with analgesic properties. It binds to opioid receptors (Ki values = 7.2, 31, and 5.7 nM for κ-, δ-, μ-opioid receptors, respectively) and to the type 1 σ-receptor (Kd = 12 nM). (?)-Pentazocine is abused with methylphenidate and other drugs. It is regulated as a Schedule IV compound in the United States. This product is intended for forensic and research applications.

Definition

ChEBI: Pentazocine is a benzazocine.

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.

brand name

Talwin (Sanofi Aventis);Fortagesic;Fortalgesic;Fortralin;Fortwin;Pentafen;Pentalgina;Talacen;Talwin nx.

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)

General Description

The benzomorphans are prepared synthetically and thus resultin several stereoisomers. The active benzomorphans arethose that have the equivalent bridgehead carbons in thesame absolute configuration of morphine (carbons 9, 13,and 14 of morphine). The only benzomorphan in clinical useis pentazocine, which is prepared as the 2(R), 6(R), 11(R)enantiomer (Chemical Abstracts numbering). Pentazocineis a mixed agonist/antagonist displaying differing intrinsicactivity at the opioid receptor subtypes. At the κ-receptor,pentazocine is a partial agonist and a weak antagonist.
According to the manufacturer, a 50-mg dose of pentazocinehas about the same analgesic potency as 60 mg of codeineand about 1/50th the antagonistic activity of nalorphine.74Pentazocine is also an agonist at the κ-receptor, and thismay be responsible for the higher percentage of patients thatexperience dysphoria with pentazocine versus morphine.75Some evidence also exists that women respond better to κ-agonists than men. Pentazocine is available in a 50-mgtablet along with a low dose of the antagonist naloxone 0.5mg (Talwin NX). Naloxone 0.5 mg orally is expected tohave no pharmacological effect but is included to dissuadeIV drug abusers from dissolving and injecting Talwin NX.

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.

PENTAZOCINE Preparation Products And Raw materials

Raw materials

Preparation Products

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PENTAZOCINE Suppliers

359-83-1, PENTAZOCINERelated Search:


  • C07421
  • Pentazocine CIV (500 mg)
  • 2,6-Methano-3-benzazocin-8-ol,1,2,3,4,5,6-hexahydro-6,11-diMethyl-3-(3-Methyl-2-buten-1-yl)-,(2R,6R,11R)-rel-
  • Pentazocine solution
  • PENTAZOCINE
  • (2alpha,6alpha,11r*)-2-butenyl)
  • (2R*,6R*,11R*)-1,2,3,4,5,6-Hexahydro-6,11-dimethyl-3-(3-methyl-2-butenyl)-2,6-methano-3-benzazocin-8-ol
  • 1,2,3,4,5,6-hexahydro-6,11-dimethyl-3-(3-methyl-2-butenyl)-2,6-methano-3-benza
  • 2-(3,3-Dimethylallyl)-2',2'-hydroxy-5,9-dimethyl-6,7-benzomorphan
  • 2-(3,3-dimethylallyl)-2’,2’-hydroxy-5,9-dimethyl-6,7-benzomorphan
  • 2-(3,3-Dimethylallyl)cyclazocine
  • 2,6-Methano-3-benzazocin-8-ol, 1,2,3,4,5,6-hexahydro-6,11-dimethyl-3-(3-methyl-2-butenyl)-
  • 2,6-Methano-3-benzazocin-8-ol, 1,2,3,4,5,6-hexahydro-6,11-dimethyl-3-(3-methyl-2-butenyl)-, (2alpha,6alpha,11R)-
  • 2,6-Methano-3-benzazocin-8-ol, 1,2,3,4,5,6-hexahydro-6,11-dimethyl-3-(3-methyl-2-butenyl)-, (2alpha,6alpha,11R*)-
  • 2’-hydroxy-5,9-dimethyl-2-(3,3-dimethylallyl)-6,7-benzomorphan
  • 2-butenyl)-
  • 2-dimethylallyl-5,9-dimethyl-2’-hydroxybenzomorphan
  • 2-Dimethylallyl-5,9-dimethyl-2'-hydroxybenzomorphan
  • 2'-Hydroxy-5,9-dimethyl-2-(3,3-dimethylallyl)-6,7-benzomorphan
  • 3-(3-methyl-2-butenyl)-1,2,3,4,5,6-hexahydro-6,11-dimethyl-2,6-methano-3-ben
  • 3-(3-methyl-2-butenyl)-1,2,3,4,5,6-hexahydro-6,11-dimethyl-2,6-methano-3-benza
  • 3-(3-Methyl-2-butenyl)-1,2,3,4,5,6-hexahydro-6,11-dimethyl-2,6-methano-3-benzazocin-8-ol
  • 6r*,11r*)-1,2,3,4,5,6-hexahydro-6,11-dimethyl-3-(3-methyl-2-butenyl)-2,6-(2r
  • dl-2’-hydroxy-5,9-dimethyl-2-(3,3-dimethylallyl)-6,7-benzomorphan
  • dl-2'-Hydroxy-5,9-dimethyl-2-(3,3-dimethylallyl)-6,7-benzomorphan
  • Fortalgesic
  • cis-(-Pentazocine
  • Win 2022
  • Pentazocinum
  • 1,2,3,4,5,6-Hexahydro-3-(3-methyl-2-butenyl)-6,11-dimethyl-8-hydroxy-2,6-methano-3-benzazocine
  • 1,2,3,4,5,6-Hexahydro-6,11-dimethyl-3-(3-methyl-2-butenyl)-2,6-methano-3-benzazocin-8-ol
  • 2,6-Methano-3-benzazocin-8-ol, 1,2,3,4,5,6-hexahydro-6,11-dimethyl-3-(3-methyl-2-butenyl)-, (2a,6a,11R*)- (8CI)
  • 2,6-Methano-3-benzazocin-8-ol, 1,2,3,4,5,6-hexahydro-6,11-dimethyl-3-(3-methyl-2-butenyl)-, (2R,6R,11R)-rel- (9CI)
  • 3-(3-Methyl-2-butenyl)-1,2,3,4,5,6-hexahydro-8-hydroxy-6,11-dimethyl-2,6-methano-3-benzazocine
  • dl-Pentazocine
  • Lexir
  • Peltazon
  • Pentazocine (base and/or unspecified salts)
  • OQGYMIIFOSJQSF-DTOXXUQYSA-N
  • Fortalin
  • Fortral
  • II-C-2
  • KF-1820
  • Liticon
  • L-pentazocine
  • methano-3-benzazocin-8-ol
  • NIH 7958
  • nih7958
  • NSC-107430
  • Pentagin
  • Pentazocaine
  • Pentazocin
  • sosegon
  • Soseton
  • Sosigon
  • Talwan
  • Talwin
  • Win 20228