469-62-5

Basic information

• Product Name: PROPOXYPHENE
• Synonyms: (+)-PROPOXYPHENE;PROPOXYPHENE;(+)-1,2-diphenyl-2-propionoxy-3-methyl-4-dimethylaminobutane;(+)-4-(Dimethylamino)-3-methyl-1,2-diphenyl-2-butanol propionate;(+)-4-dimethylamino-1,2-diphenyl-3-methyl-2-propionyloxybutane;(+)-propoxyphen;(2S,3R)-(+)-4-(Dimethylamino)-3-methyl-1,2-diphenyl-2-butanol propionate(ester);(s-(r*,s*))-te(ester
• CAS NO: 469-62-5
• Molecular Formula: C₂₂H₂₉NO₂
• Molecular Weight: 339.47
• EINECS: 207-420-5
• Mol File: 469-62-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 75-76°
• Boiling Point: 475.43°C (rough estimate)
• Flash Point: 2℃
• Appearance: white crystalline powder
• Density: 1.0751 (rough estimate)
• Refractive Index: 1.5614 (estimate)
• Storage Temp.: 2-8°C
• PKA: pKa 6.3(50% aq EtOH) (Uncertain)
• CAS DataBase Reference: PROPOXYPHENE(CAS DataBase Reference)
• NIST Chemistry Reference: PROPOXYPHENE(469-62-5)
• EPA Substance Registry System: PROPOXYPHENE(469-62-5)

Safety Data

• Hazard Codes: F,Xn,T
• Statements: 11-20/21/22-36-52/53-25
• Safety Statements: 16-26-36/37-61-45-36/37/39
• RIDADR: 3249
• WGK Germany: 2
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 469-62-5(Hazardous Substances Data)

Usage

Description

PROPOXYPHENE is a derivative of methadone, an opioid analgesic, which was marketed in 1957. It is approximately 1/10th as potent as morphine but retains the same opioid adverse effects. The drug is available in the form of hydrochloride salt (Darvon), napsylate salt (Darvon-N), and in combination with other medications such as acetaminophen (Darvocet, Darvocet-N) and a combination of propoxyphene, aspirin, and caffeine.

Uses

1. Used in Pain Management:
PROPOXYPHENE is used as an analgesic for the relief of mild to moderate pain. One propoxyphene 65-mg capsule has the same analgesic effect as 650 mg of aspirin or 1,000 mg of acetaminophen. However, it is crucial for patients to follow the prescribed dose to avoid overdoses.
2. Used in Combination Therapy:
PROPOXYPHENE is used in combination with other medications, such as acetaminophen, to enhance its analgesic effects and provide additional pain relief.
3. Used in Pharmaceutical Formulations:
The hydrochloride salt of PROPOXYPHENE is marketed as Darvon, and the napsylate salt as Darvon-N. These salts are also available in combination with acetaminophen (Darvocet, Darvocet-N) and a propoxyphene, aspirin, and caffeine product.

Biological Functions

Propoxyphene (dextropropoxyphene; Darvon) is structurally related to methadone but is much less potent as an analgesic. Compared with codeine, propoxyphene is approximately half as potent and is indicated for the treatment of mild pain. It is not antipyretic or antiinflammatory like aspirin and is less useful than aspirin in most cases of mild pain. Toxicity from propoxyphene, especially in combination with other sedatives, such as alcohol, has led to a decrease in its use. Death following ingestion of alcohol in combination with propoxyphene can occur rapidly (within 20 minutes to 1 hour). The drug is not indicated for those with histories of suicide or depressive illnesses. Like meperidine, propoxyphene has an active metabolite, norpropoxyphene, that is not analgesic but has excitatory and local anesthetic effects on the heart similar to those of quinidine. Use of the drug during pregnancy is not safe.Teratogenic effects have been observed in newborns, as have withdrawal signs at birth. As with morphine, propoxyphene requires adequate hepatic and renal clearance to prevent toxicity and drug accumulation. It is thus contraindicated in the elderly patient and those with renal or liver disease. Propoxyphene interacts with several drugs. The use of sedatives in combination with propoxyphene can be fatal. In addition, the metabolism of the drug is increased in smokers due to induction of liver enzymes. Thus, smokers may require a higher dose of the drug for pain relief. Propoxyphene enhances the effects of both warfarin and carbamazepine and may increase the toxicity associated with both drugs, such as bleeding and sedation, respectively.The abuse liability of propoxyphene is low because of the extreme irritation it causes at the site of injection. Oral use is the preferred route of administration for this reason.

Safety Profile

Poison by ingestion, intraperitoneal, subcutaneous, and intravenous routes. Human systemic effects by ingestion: change in cardiac rate, respiratory depression, and coma. When heated to decomposition it emits toxic fumes of NOx.

InChI:InChI=1/C22H29NO2/c1-5-21(24)25-22(18(2)17-23(3)4,20-14-10-7-11-15-20)16-19-12-8-6-9-13-19/h6-15,18H,5,16-17H2,1-4H3/t18-,22+/m1/s1

Downstream Products

• 136984-51-5 (2S)-2,3-diphenyl-2-hydroxypropanoic acid 
• 19643-66-4 (S)-2,3-diphenyl-1-propanol 
• 83026-52-2 methyl (S)-(+)-2,3-diphenyl-2-hydroxypropionate 
• 58714-11-7 (S)-2,3-diphenyl-propionic acid methyl ester 
• 63463-58-1 (1S,2R)-2-methyl-1-phenyl-1-(phenylmethyl)-1,3-propanediol 

Relevant articles and documents

Use of weak opioids and mixed opioid agonists/antagonists for treatment of urinary incontinence

A pharmaceutical composition for the treatment of an increased urge to urinate or urinary incontinence, comprising an effective amount of at least a compound selected from the group consisting of codeine, dihydrocodeine, dextropropoxyphene, meptazinol and tilidine. Also disclosed are methods of treatment using the pharmaceutical compositions and preferred dosages for the treatment methods.

Polypeptide propoxyphene derivatives for immunoassay reagents

Novel compounds are provided which are derivatives of 1,2-diphenyl-3-methyl-4-dimethylamino-2-butanol. The indicated alcohol is employed to prepare the monoester of a dibasic acid which is conjugated with an antigen for the production of antibodies which recognize both propoxyphene and its N-desmethyl metabolite in immunoassays.