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Substance Name: Pentazocine [USAN:USP:INN:BAN:JAN]
RN: 359-83-1
UNII: RP4A60D26L
InChIKey: VOKSWYLNZZRQPF-CCKFTAQKSA-N

Note

  • The first mixed agonist-antagonist analgesic to be marketed. It is an agonist at the kappa and sigma opioid receptors and has a weak antagonist action at the mu receptor. (From AMA Drug Evaluations Annual, 1991, p97)

Molecular Formula

  • C19-H27-N-O

Molecular Weight

  • 285.4283
 

Classification Codes

Classification Codes

  • Adjuvants, Anesthesia
  • Analgesic
  • Analgesics
  • Analgesics, Opioid
  • Central Nervous System Agents
  • Central Nervous System Depressants
  • Drug / Therapeutic Agent
  • Human Data
  • Narcotic Antagonists
  • Narcotics
  • Peripheral Nervous System Agents
  • Reproductive Effect
  • Sensory System Agents

Superlist Classification Code

  • DEA Schedule IV

Names and Synonyms

Name of Substance

  • Pentazocine
  • Pentazocine [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Pentazocine

Synonyms

  • (+-)-Pentazocine
  • (2R*,6R*,11R*)-1,2,3,4,5,6-Hexahydro-6,11-dimethyl-3-(3-methyl-2-butenyl)-2,6-methano-3-benzazocin-8-ol
  • 1,2,3,4,5,6-Hexahydro-6,11-dimethyl-3-(3-methyl-2-butenyl)-2,6-methano-3-benzazocin-8-ol
  • 2'-Hydroxy-5,9-dimethyl-2-(3,3-dimethylallyl)-6,7-benzomorphan
  • 2,6-Methano-3-benzazocin-8-ol, 1,2,3,4,5,6-hexahydro-6,11-dimethyl-3-(3-methyl-2-butenyl)-
  • 2-(3,3-Dimethylallyl)-2',2'-hydroxy-5,9-dimethyl-6,7-benzomorphan
  • 2-(3,3-Dimethylallyl)cyclazocine
  • 2-Dimethylallyl-5,9-dimethyl-2'-hydroxybenzomorphan
  • 3-(3-Methyl-2-butenyl)-1,2,3,4,5,6-hexahydro-6,11-dimethyl-2,6-methano-3-benzazocin-8-ol
  • cis-(+-)-Pentazocine
  • dl-Pentazocine
  • EINECS 206-634-6
  • Fortalgesic
  • Fortalin
  • Fortral
  • HSDB 3150
  • II-C-2
  • KF-1820
  • Liticon
  • NIH 7958
  • NSC 107430
  • NSC-107430
  • Pentagin
  • Pentazocin
  • Pentazocina
  • Pentazocina [DCIT]
  • Pentazocine
  • Pentazocinum
  • Pentazocinum [INN-Latin]
  • Sosegon
  • Sosigon
  • Talwin
  • UNII-RP4A60D26L
  • Win 20,228
  • WIN 20228

Systematic Names

  • 2,6-Methano-3-benzazocin-8-ol, 1,2,3,4,5,6-hexahydro-6,11-dimethyl-3-(3-methyl-2-butenyl)-, (2alpha,6alpha,11R*)-
  • Pentazocine

Superlist Names

  • DEA No. 9709
  • Pentazocine

Registry Numbers

CAS Registry Number

  • 359-83-1

FDA UNII

  • RP4A60D26L

Other Registry Numbers

  • 10535-38-3
  • 16760-69-3
  • 16760-70-6
  • 21820-34-8
  • 3411-11-8
  • 6654-32-6
  • 6654-33-7
  • 7313-81-7

Related Registry Numbers

  • 17146-95-1 (lactate)
  • 64024-15-3 (hydrochloride)

System Generated Number

  • 0000359831

Structure Descriptors

InChI

1S/C19H27NO/c1-13(2)7-9-20-10-8-19(4)14(3)18(20)11-15-5-6-16(21)12-17(15)19/h5-7,12,14,18,21H,8-11H2,1-4H3/t14-,18+,19+/m1/s1

InChIKey

VOKSWYLNZZRQPF-CCKFTAQKSA-N

Smiles

C[C@@H]1[C@@H]2Cc3ccc(O)cc3[C@@]1(C)CCN2CC=C(C)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human LDLo oral 18mg/kg (18mg/kg) LUNGS, THORAX, OR RESPIRATION: BRONCHIECTASIS Clinical Toxicology. Vol. 10, Pg. 327, 1977.
human TDLo intramuscular 571ug/kg (0.571mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: EUPHORIA
Journal of Pharmacology and Experimental Therapeutics. Vol. 143, Pg. 149, 1964.
human TDLo intravenous 300mg/kg/D (300mg/kg) BEHAVIORAL: ANALGESIA

BEHAVIORAL: WITHDRAWAL
British Medical Journal. Vol. 2, Pg. 21, 1978.
mammal (species unspecified) LD50 intraperitoneal 140mg/kg (140mg/kg)   United States Patent Document. Vol. #4205173,
man TDLo intramuscular 83mg/kg/4Y-I (83mg/kg) MUSCULOSKELETAL: JOINTS Archives of Internal Medicine. Vol. 143, Pg. 2203, 1983.
man TDLo intravenous 3mg/kg/2D-I (3mg/kg) BEHAVIORAL: EXCITEMENT

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: WAKEFULNESS
Journal of Pharmacology and Experimental Therapeutics. Vol. 143, Pg. 149, 1964.
mouse LD50 intramuscular 98mg/kg (98mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 190, Pg. 124, 1971.
mouse LD50 intraperitoneal 85mg/kg (85mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: ANALGESIA

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Chemical and Pharmaceutical Bulletin. Vol. 24, Pg. 2912, 1976.
mouse LD50 intravenous 19800ug/kg (19.8mg/kg)   Drugs in Japan Vol. 6, Pg. 777, 1982.
mouse LD50 oral 305mg/kg (305mg/kg)   Acta Medicia Okayama. Vol. 35, Pg. 179, 1981.
mouse LD50 subcutaneous 140mg/kg (140mg/kg)   Acta Medicia Okayama. Vol. 35, Pg. 179, 1981.
rat LD50 intramuscular 175mg/kg (175mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 190, Pg. 124, 1971.
rat LD50 intravenous 21mg/kg (21mg/kg)   "Synthetic Analgesics," Oxford, Pergamon Press, 1966Vol. 2, Pg. 174, 1966.
rat LD50 oral 1110mg/kg (1110mg/kg) BEHAVIORAL: TREMOR

AUTONOMIC NERVOUS SYSTEM: OTHER (DIRECT) PARASYMPATHOMIMETIC

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Kiso to Rinsho. Clinical Report. Vol. 4, Pg. 2145, 1970.
rat LD50 subcutaneous 165mg/kg (165mg/kg)   Acta Medicia Okayama. Vol. 35, Pg. 179, 1981.
rat LD50 unreported 280mg/kg (280mg/kg) BEHAVIORAL: ANALGESIA Pharmacological Research Communications. Vol. 5, Pg. 175, 1973.
women TDLo intramuscular 1400mg/kg/3Y (1400mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
JAMA, Journal of the American Medical Association. Vol. 231, Pg. 271, 1975.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 146.3 deg C   EXP
pKa Dissociation Constant 8.88 (none)   EXP
log P (octanol-water) 4.64 (none)   EXP
Atmospheric OH Rate Constant 2.95E-10 cm3/molecule-sec 25 EST

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