Propoxyphene (CHEM002237)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (10)XML
Record Information
Version1.0
Creation Date2009-07-21 20:27:20 UTC
Update Date2026-05-14 16:44:59 UTC
Accession NumberCHEM002237
Identification
Common NamePropoxyphene
ClassSmall Molecule
DescriptionPropoxyphene is only found in individuals that have used or taken this drug. It is a narcotic analgesic structurally related to methadone. Only the dextro-isomer has an analgesic effect; the levo-isomer appears to exert an antitussive effect. [PubChem]Propoxyphene acts as a weak agonist at OP1, OP2, and OP3 opiate receptors within the central nervous system (CNS). Propoxyphene primarily affects OP3 receptors, which are coupled with G-protein receptors and function as modulators, both positive and negative, of synaptic transmission via G-proteins that activate effector proteins. Binding of the opiate stimulates the exchange of GTP for GDP on the G-protein complex. As the effector system is adenylate cyclase and cAMP located at the inner surface of the plasma membrane, opioids decrease intracellular cAMP by inhibiting adenylate cyclase. Subsequently, the release of nociceptive neurotransmitters such as substance P, GABA, dopamine, acetylcholine, and noradrenaline is inhibited. Opioids such as propoxyphene also inhibit the release of vasopressin, somatostatin, insulin, and glucagon. Opioids close N-type voltage-operated calcium channels (OP2-receptor agonist) and open calcium-dependent inwardly rectifying potassium channels (OP3 and OP1 receptor agonist). This results in hyperpolarization and reduced neuronal excitability.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amine
  • Analgesic
  • Analgesic, Opioid
  • Antitussive Agent
  • Drug
  • Ester
  • Ether
  • Metabolite
  • Narcotic
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-4-(Dimethylamino)-3-methyl-1,2-diphenyl-2-(propionyloxy)butaneChEBI
(-)-PropoxypheneChEBI
(R)-alpha-(2-(Dimethylamino)-1-methylethyl)-alpha-phenylbenzeneethanol propanoateChEBI
L-PropoxypheneChEBI
LevopropossifeneChEBI
LevopropoxifenoChEBI
LevopropoxyphenumChEBI
(R)-a-(2-(Dimethylamino)-1-methylethyl)-a-phenylbenzeneethanol propanoateGenerator
(R)-a-(2-(Dimethylamino)-1-methylethyl)-a-phenylbenzeneethanol propanoic acidGenerator
(R)-alpha-(2-(Dimethylamino)-1-methylethyl)-alpha-phenylbenzeneethanol propanoic acidGenerator
(R)-Α-(2-(dimethylamino)-1-methylethyl)-α-phenylbenzeneethanol propanoateGenerator
(R)-Α-(2-(dimethylamino)-1-methylethyl)-α-phenylbenzeneethanol propanoic acidGenerator
LevopropoxypheneMeSH
Propoxyphene hydrochloride, (r*,s*)-(+-)-isomerMeSH
Propoxyphene, (r*,s*)-(+-)-isomerMeSH
Propoxyphene, (R-(r*,s*))-isomerMeSH
Chemical FormulaC22H29NO2
Average Molecular Mass339.479 g/mol
Monoisotopic Mass339.220 g/mol
CAS Registry Number469-62-5
IUPAC Name(2S,3R)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl propanoate
Traditional Namelevopropoxyphene
SMILES[H][C@](C)(CN(C)C)[C@@](CC1=CC=CC=C1)(OC(=O)CC)C1=CC=CC=C1
InChI IdentifierInChI=1S/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+/m0/s1
InChI KeyXLMALTXPSGQGBX-PGRDOPGGSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • Phenylbutylamine
  • Benzyloxycarbonyl
  • Phenylpropane
  • Aralkylamine
  • Monocyclic benzene moiety
  • Benzenoid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid ester
  • Amino acid or derivatives
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point75.5°C
Boiling PointNot Available
Solubility3.32 mg/L (at 25°C)
Predicted Properties
PropertyValueSource
Water Solubility0.0042 g/LALOGPS
logP4.06ALOGPS
logP4.9ChemAxon
logS-4.9ALOGPS
pKa (Strongest Basic)9.52ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.54 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity102.88 m³·mol⁻¹ChemAxon
Polarizability38.92 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052f-5097000000-14ee532e398ad87fafa7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aor-7391000000-99df9afa035ec5903954Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9650000000-250ef3abb6af95e8d3b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-3059000000-8b5a0ccf0362c5cb5fabSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0540-5194000000-be7207ca388dafc238caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-9270000000-ca80d8ae975fd75212c7Spectrum
Toxicity Profile
Route of ExposureOral
Mechanism of ToxicityPropoxyphene acts as a weak agonist at OP1, OP2, and OP3 opiate receptors within the central nervous system (CNS). Propoxyphene primarily affects OP3 receptors, which are coupled with G-protein receptors and function as modulators, both positive and negative, of synaptic transmission via G-proteins that activate effector proteins. Binding of the opiate stimulates the exchange of GTP for GDP on the G-protein complex. As the effector system is adenylate cyclase and cAMP located at the inner surface of the plasma membrane, opioids decrease intracellular cAMP by inhibiting adenylate cyclase. Subsequently, the release of nociceptive neurotransmitters such as substance P, GABA, dopamine, acetylcholine, and noradrenaline is inhibited. Opioids such as propoxyphene also inhibit the release of vasopressin, somatostatin, insulin, and glucagon. Opioids close N-type voltage-operated calcium channels (OP2-receptor agonist) and open calcium-dependent inwardly rectifying potassium channels (OP3 and OP1 receptor agonist). This results in hyperpolarization and reduced neuronal excitability.
MetabolismHepatic 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
Toxicity ValuesLD50: 230mg/kg (oral, rat)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the relief of mild to moderate pain
Minimum Risk LevelNot Available
Health EffectsMedical problems can include congested lungs, liver disease, tetanus, infection of the heart valves, skin abscesses, anemia and pneumonia. Death can occur from overdose.
SymptomsComa, respiratory depression, circulatory collapse, and pulmonary edema. Seizures occur more frequently in patients with propoxyphene intoxication than in those with opiate intoxication.
TreatmentAttention 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. (3)
Concentrations
Not Available
DrugBank IDDB06793
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkLevopropoxyphene
Chemspider IDNot Available
ChEBI ID51174
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Carl R. White, “Synthesis and purification of d-propoxyphene hydrochloride.” U.S. Patent US4661625, issued April, 1973.

MSDSLink
General ReferencesNot Available