Basic information
- CAS
1639-60-7- Standard SMILES
CCC(=O)O[C@](Cc1ccccc1)(c1ccccc1)[C@H](C)CN(C)C.Cl- InChIKey
QMQBBUPJKANITL-MYXGOWFTSA-N- Molecular formula
- C22H30ClNO2
- Average molar mass
- 375.9 g/mol
- Monoisotopic mass
- 375.1965069
Overview
Propoxyphene Hydrochloride is the hydrochloride salt form of the d-isomer of synthetic diphenyl propionate derivative propoxyphene, with narcotic analgesic effect. This agent mimics the effects of the endogenous opiate dextropropoxyphene, by binding to mu receptors located throughout the central nervous system. The binding results in GTP to GDP exchanges on the mu-G-protein complex, by which effector adenylate cyclase is inactivated thereby decreasing intracellular cAMP. This, in turn, inhibits the release of various nociceptive neurotransmitters, such as substance P, gamma-aminobutyric acid (GABA), dopamine, acetylcholine, noradrenaline, vasopressin, and somatostatin. In addition, dextropropoxyphene closes N-type voltage-gated calcium channels and opens calcium-dependent inwardly rectifying potassium channels. This results in hyperpolarization, thereby reducing neuronal excitability, which further decreases the perception of pain.
Names & identifiers
- Preferred name
- Dextropropoxyphene Hydrochloride
- IUPAC
- [(2S,3R)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;hydrochloride
Names & synonyms
Propoxyphene hydrochlorideDeprancolAlgaphanDextropropoxyphene hydrochloridePropoxyphene HCl1639-60-7DoleneKesso-GesicDepronalDolotardDoloxeneProphene 65
Show more names
DoraphenAbalginZideronFemadolHarmar(+)-Propoxyphene hydrochlorided-Propoxyphene monohydrochlorideDTXSID6048913
Database identifiers
- CAS
1639-60-7- PubChem CID
- 15424
- DTXSID
DTXSID6048913- ChEMBL
CHEMBL1237104- UNII
- CB2TL9PS0T
- EC Number
- 216-683-5
Properties
Computed structural properties
- Topological polar surface area
- 29.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 9
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 397
Experimental & physicochemical properties
Human Drugs
Breast Feeding; Lactation; Milk, Human; Analgesics, Opioid; Narcotics
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 47 reports by companies from 6 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory InformationBenzeneethanol, .alpha.-(1R)-2-(dimethylamino)-1-methylethyl-.alpha.-phenyl-, propanoate (ester), hydrochloride, (.alpha.S)-: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - Benzeneethanol, .alpha.-[2-(dimethylamino)-1-methylethyl]-.alpha.-phenyl-, propanoate (ester), hydrochloride, [S-(R*,S*)]-: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 3 (100%)
Toxicology
Treatment
Attention should be directed first to establishing a patent airway and to restoring ventilation. Mechanically assisted ventilation, with or without oxygen, may be required, and positive pressure respiration may be desirable if pulmonary edema is present. The narcotic antagonist naloxone will markedly reduce the degree of respiratory depression, and 0.4 to 2 mg should be administered promptly, preferably intravenously. If the desired degree of counteraction with improvement in respiratory functions is not obtained, naloxone should be repeated at 2- to 3-minute intervals. The duration of action of the antagonist may be brief. If no response is observed after 10 mg of naloxone have been administered, the diagnosis of propoxyphene toxicity should be questioned. Naloxone may also be administered by continuous intravenous infusion. (L1712)
Chemistry & industry
Pharmacology
Metabolism/Metabolites
Hepatic Route of Elimination: The major route of metabolism is cytochrome CYP3A4 mediated N-demethylation to norpropoxyphene, which is excreted by the kidneys. In 48 hours, approximately 20% to 25% of the administered dose of propoxyphene is excreted via the urine, most of which is free or conjugated norpropoxyphene. Half Life: 6-12 hours
MeSH Pharmacological Classification
Compounds with activity like OPIATE ALKALOIDS, acting at OPIOID RECEPTORS. Properties include induction of ANALGESIA or NARCOSIS.
Agents that induce NARCOSIS. Narcotics include agents that cause somnolence or induced sleep (STUPOR); natural or synthetic derivatives of OPIUM or MORPHINE or any substance that has such effects. They are potent inducers of ANALGESIA and OPIOID-RELATED DISORDERS.
Uses & manufacturing
UsesFor the relief of mild to moderate pain
General Manufacturing InformationBenzeneethanol, .alpha.-[(1R)-2-(dimethylamino)-1-methylethyl]-.alpha.-phenyl-, 1-propanoate, hydrochloride (1:1), (.alpha.S)-: INACTIVE
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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