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Substance Name: Dextropropoxyphene [INN:BAN]
RN: 469-62-5
UNII: S2F83W92TK
InChIKey: XLMALTXPSGQGBX-GCJKJVERSA-N

Note

  • A narcotic analgesic structurally related to METHADONE. Only the dextro-isomer has an analgesic effect; the levo-isomer appears to exert an antitussive effect.

Molecular Formula

  • C22-H29-N-O2

Molecular Weight

  • 339.476
 

Classification Codes

Classification Codes

  • Analgesics
  • Analgesics, Opioid
  • Central Nervous System Agents
  • Central Nervous System Depressants
  • Drug / Therapeutic Agent
  • Human Data
  • Narcotics
  • Peripheral Nervous System Agents
  • Sensory System Agents

Superlist Classification Code

  • DEA Schedule II
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Names and Synonyms

Name of Substance

  • (d)-Propoxyphene
  • Dextropropoxyphene [INN:BAN]
  • Propoxyphene

MeSH Heading

  • Dextropropoxyphene

Synonyms

  • (+)-1,2-Diphenyl-2-propionoxy-3-methyl-4-dimethylaminobutane
  • (+)-4-Dimethylamino-1,2-diphenyl-3-methyl-2-propionyloxybutane
  • (S)-alpha-(2-(Dimethylamino)-1-methylethyl)-alpha-phenylbenzeneethanol propanoate
  • 2-Butanol, 4-(dimethylamino)-3-methyl-1,2-diphenyl-, propionate (ester), (2S,3R)-
  • 4-Dimethylamino-3-methyl-1,2-diphenyl-2-propoxybutane
  • Algafan
  • alpha-(+)-4-Dimethylamino-1,2-diphenyl-3-methyl-2-butanol propionate ester
  • alpha-4-Dimethylamino-1,2-diphenyl-3-methyl-2-butanol propionate
  • alpha-D-4-Dimethylamino-3-methyl-1,2-diphenyl-2-butanol propionate
  • alpha-D-4-Dimethylamino-3-methyl-1,2-diphenyl-2-butanol-propionat
  • alpha-D-4-Dimethylamino-3-methyl-1,2-diphenyl-2-butanol-propionat [German]
  • Antalvic
  • Benzeneethanol, alpha-(2-(dimethylamino)-1-methylethyl)-alpha-phenyl-, propanoate (ester), (S-(R*,S*))-
  • d-Propoxyphene
  • Destropropossifene
  • Destropropossifene [DCIT]
  • Dextropropoxifeno
  • Dextropropoxifeno [INN-Spanish]
  • Dextropropoxyphen
  • Dextropropoxyphene
  • Dextropropoxyphenum
  • Dextropropoxyphenum [INN-Latin]
  • Dextroproxifeno
  • Dextroproxifeno [Spanish]
  • EINECS 207-420-5
  • Femadol
  • HSDB 3175
  • Propoxyphene
  • Propoxyphene, (+)-
  • Proxagesic
  • Proxyvon
  • SK 65
  • UNII-S2F83W92TK

Systematic Names

  • 2-Butanol, 4-(dimethylamino)-3-methyl-1,2-diphenyl-, propionate, (+)-
  • Benzeneethanol, alpha-((1R)-2-(dimethylamino)-1-methylethyl)-alpha-phenyl-, propanoate (ester), (alphaS)-
  • Benzeneethanol, alpha-(2-(dimethylamino)-1-methylethyl)-alpha-phenyl-, propanoate (ester), (S-(R*,S*))-
  • Dextropropoxyphene

Superlist Names

  • alpha-(+)-4-Dimethylamino-1,2-diphenyl-3-methyl-2-propionoxybutane
  • Bulk dextropropoxyphene (non-dosage forms)
  • DEA No. 9273
  • Dextropropoxyphene

Registry Numbers

CAS Registry Number

  • 469-62-5

FDA UNII

  • S2F83W92TK

Other Registry Numbers

  • 21086-94-2
  • 3818-94-8

System Generated Number

  • 0000469625

Structure Descriptors

InChI

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+/m1/s1

InChIKey

XLMALTXPSGQGBX-GCJKJVERSA-N

Smiles

O(C(CC)=O)[C@@](c1ccccc1)(Cc1ccccc1)[C@@H](CN(C)C)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TDLo oral 650mg/kg (650mg/kg) CARDIAC: CHANGE IN RATE

BEHAVIORAL: COMA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Acta Medica Scandinavica. Vol. 200, Pg. 241, 1976.
mouse LD50 intraperitoneal 110mg/kg (110mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: ANTIPSYCHOTIC

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 178, Pg. 446, 1969.
mouse LD50 intravenous 25mg/kg (25mg/kg) BEHAVIORAL: ANALGESIA Archives Internationales de Pharmacodynamie et de Therapie. Vol. 134, Pg. 154, 1961.
mouse LD50 oral 140mg/kg (140mg/kg)   United States Patent Document. Vol. #4198424,
mouse LD50 subcutaneous 113mg/kg (113mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 24, Pg. 600, 1974.
rat LD50 intraperitoneal 50mg/kg (50mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: CYANOSIS

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 178, Pg. 446, 1969.
rat LD50 oral 135mg/kg (135mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: CYANOSIS

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 178, Pg. 446, 1969.
rat LD50 subcutaneous 79100ug/kg (79.1mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 24, Pg. 600, 1974.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 75.5 deg C   EXP
log P (octanol-water) 4.18 (none)   EXP
Water Solubility 3.32 mg/L 25 EXP
Vapor Pressure 5.54E-07 mm Hg 25 EST
Henry's Law Constant 2.34E-09 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 9.88E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.