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Substance Name: Alphaprodine hydrochloride [USP]
RN: 561-78-4
UNII: CO51Q2EI5Z
InChIKey: LFLUADVCIBEPQJ-MELYUZJYSA-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.Cl-H

Molecular Weight

  • 297.8236
 

Classification Codes

  • Drug / Therapeutic Agent
  • Human Data
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Names and Synonyms

Name of Substance

  • Alphaprodine hydrochloride [USP]
  • Alphaprodine, dl- hydrochloride

Synonyms

  • (+-)-1,3-Dimethyl-4-phenyl-4-piperidinol propionate (ester) hydrochloride
  • (+-)-alpha-1,3-Dimethyl-4-phenyl-4-propionoxypiperidine hydrochloride
  • 1,3-Dimethyl-4-phenyl-4-piperidyl propionate hydrochloride
  • 4-Piperidinol, 1,3-dimethyl-4-phenyl-, propionate, hydrochloride
  • alpha-Prodine hydrochloride
  • Alphaprodine hydrochloride
  • dl-1,3-Dimethyl-4-phenyl-4-piperidinol propionate hydrochloride
  • Nisentil
  • Nisentil hydrochloride
  • NU-1196
  • Prisilidene hydrochloride
  • Propionic acid, 1,3-dimethyl-4-phenyl-4-piperidyl ester, hydrochloride, (+-)-
  • UNII-CO51Q2EI5Z

Systematic Names

  • 4-Piperidinol, 1,3-dimethyl-4-phenyl-, propanoate (ester), hydrochloride, cis-(+-)-
  • 4-Piperidinol, 1,3-dimethyl-4-phenyl-, propionate, hydrochloride, (+-)-

Registry Numbers

CAS Registry Number

  • 561-78-4

FDA UNII

  • CO51Q2EI5Z

Other Registry Numbers

  • 17046-72-9
  • 49638-24-6
  • 58052-60-1

Related Registry Number

  • 77-20-3 (Parent)

System Generated Number

  • 0000561784

Molecular Formulas

Molecular Formula

  • C16-H23-N-O2.Cl-H

Molecular Formula Fragments

  • C16-H23-N-O2
  • Cl-H
  • COMPONENT

Structure Descriptors

InChI

1S/C16H23NO2.ClH/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;1H/t13-,16+;/m0./s1

InChIKey

LFLUADVCIBEPQJ-MELYUZJYSA-N

Smiles

CCC(=O)O[C@@]1(CC[N@@](C[C@@H]1C)C)c2ccccc2.Cl

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous 36200ug/kg (36.2mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 109, Pg. 171, 1957.
human LDLo oral 1440ug/kg (1.44mg/kg) BEHAVIORAL: TREMOR

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BLOOD: HEMORRHAGE
Clinical Toxicology. Vol. 5, Pg. 307, 1972.
mouse LD50 intraperitoneal 73mg/kg (73mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE
Journal of Pharmacology and Experimental Therapeutics. Vol. 99, Pg. 312, 1950.
mouse LD50 intravenous 32mg/kg (32mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 93, Pg. 314, 1948.
mouse LD50 subcutaneous 98mg/kg (98mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Journal of Pharmacology and Experimental Therapeutics. Vol. 99, Pg. 312, 1950.
rabbit LD50 intravenous 19mg/kg (19mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE
Journal of Pharmacology and Experimental Therapeutics. Vol. 99, Pg. 312, 1950.
rat LD50 intraperitoneal 22mg/kg (22mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Journal of Pharmacology and Experimental Therapeutics. Vol. 99, Pg. 312, 1950.
rat LD50 intravenous 25mg/kg (25mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 109, Pg. 171, 1957.
rat LD50 oral 90mg/kg (90mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 93, Pg. 314, 1948.
rat LD50 subcutaneous 23mg/kg (23mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Journal of Pharmacology and Experimental Therapeutics. Vol. 99, Pg. 312, 1950.