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Substance Name: Alphaprodine [INN:BAN]
RN: 77-20-3
UNII: 001O2254AC
InChIKey: UVAZQQHAVMNMHE-XJKSGUPXSA-N

Note

  • An opioid analgesic chemically related to and with an action resembling that of MEPERIDINE, but more rapid in onset and of shorter duration. It has been used in obstetrics, as pre-operative medication, for minor surgical procedures, and for dental procedures. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1067)

Molecular Formula

  • C16-H23-N-O2

Molecular Weight

  • 261.3627
 

Classification Codes

Classification Codes

  • Analgesics
  • Analgesics, Opioid
  • Central Nervous System Agents
  • Central Nervous System Depressants
  • Narcotics
  • Peripheral Nervous System Agents
  • Sensory System Agents

Superlist Classification Code

  • DEA Schedule II
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Names and Synonyms

Name of Substance

  • Alphaprodine
  • Alphaprodine [INN:BAN]

MeSH Heading

  • Alphaprodine

Synonyms

  • (+-)-Alphaprodine
  • 1,3-Dimethyl-4-phenyl-4-piperidinol propanoate
  • 1,3-Dimethyl-4-phenyl-4-propionoxypiperidine
  • 4-Piperidinol, 1,3-dimethyl-4-phenyl-, propanoate (ester), cis-
  • 4-Piperidinol, 1,3-dimethyl-4-phenyl-, propionate
  • 4-Piperidinol, 1,3-dimethyl-4-phenyl-, propionate (ester)
  • Alfaprodina
  • Alfaprodina [INN-Spanish]
  • alpha-1,3-Dimethyl-4-phenyl-4-piperidinyl propionate
  • alpha-Prodinol
  • Alphaprodin
  • Alphaprodine
  • Alphaprodinum
  • Alphaprodinum [INN-Latin]
  • dl-alpha-Prodine
  • EINECS 201-011-5
  • HSDB 3283
  • Nisentil
  • Prisilidene
  • Prodine
  • Propionic acid, alpha-1,3-dimethyl-4-phenyl-4-piperidyl ester
  • UNII-001O2254AC

Systematic Names

  • 4-Piperidinol, 1,3-dimethyl-4-phenyl-, propanoate (ester), cis-
  • Alphaprodine

Superlist Names

  • Alphaprodine
  • DEA No. 9010

Registry Numbers

CAS Registry Number

  • 77-20-3

FDA UNII

  • 001O2254AC

Other Registry Numbers

  • 15867-21-7
  • 4618-43-3

Related Registry Number

  • 561-78-4 (hydrochloride)

System Generated Number

  • 0000077203

Structure Descriptors

InChI

1S/C16H23NO2/c1-4-15(18)19-16(14-8-6-5-7-9-14)10-11-17(3)12-13(16)2/h5-9,13H,4,10-12H2,1-3H3/t13-,16+/m0/s1

InChIKey

UVAZQQHAVMNMHE-XJKSGUPXSA-N

Smiles

CCC(=O)O[C@@]1(CCN(C)C[C@@H]1C)c2ccccc2

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 68mg/kg (68mg/kg)   Pharmacology: International Journal of Experimental and Clinical Pharmacology. Vol. 12, Pg. 39, 1974.
mouse LD50 intraperitoneal 68mg/kg (68mg/kg) BEHAVIORAL: EXCITEMENT Pharmacology: International Journal of Experimental and Clinical Pharmacology. Vol. 12, Pg. 39, 1974.

Physical Properties

Physical Property Value Units Temp (deg C) Source
pKa Dissociation Constant 8.46 (none)   EXP
log P (octanol-water) 2.83 (none)   EXP
Water Solubility 797 mg/L 25 EST
Vapor Pressure 4.37E-05 mm Hg 25 EST
Henry's Law Constant 1.28E-08 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 9.79E-11 cm3/molecule-sec 25 EST

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