Phenazocine

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Opioid analgesic

title: "Phenazocine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["benzomorphans", "hallucinogenic-kappa-opioid-receptor-agonists", "mu-opioid-receptor-agonists", "hydroxyarenes", "synthetic-opioids"] description: "Opioid analgesic" topic_path: "general/benzomorphans" source: "https://en.wikipedia.org/wiki/Phenazocine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Opioid analgesic ::

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 464200012 | IUPAC_name = (2R,6R,11R)-6,11-Dimethyl-3-(2-phenylethyl)-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocin-8-ol | image = Phenazocine2DCSD.svg | image_class = skin-invert-image | width = 220px | image2 = Phenazocine 3D BS.png | image_class2 = bg-transparent | width2 = 220px

| tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = Schedule 9 | legal_BR = A1 | legal_BR_comment = | legal_CA = Schedule I | legal_UK = Class A | legal_UK_comment = Withdrawn | legal_US = Schedule II | legal_DE = Anlage I | routes_of_administration = Oral

| bioavailability = | protein_bound = | excretion =

| CAS_number_Ref = | CAS_number = 58073-76-0 | ATC_prefix = N02 | ATC_suffix = AD02 | PubChem = 14707 | DrugBank_Ref = | DrugBank = | KEGG = C11790 | ChemSpiderID_Ref = | ChemSpiderID = 391631 | UNII_Ref = | UNII = J0ND6N0AQC | ChEMBL_Ref = | ChEMBL = 46399

| C=22 | H=27 | N=1 | O=1 | smiles = C[C@H]1[C@H]2Cc3ccc(cc3[C@@]1(CCN2CCc4ccccc4)C)O | StdInChI_Ref = | StdInChI = 1S/C22H27NO/c1-16-21-14-18-8-9-19(24)15-20(18)22(16,2)11-13-23(21)12-10-17-6-4-3-5-7-17/h3-9,15-16,21,24H,10-14H2,1-2H3/t16-,21+,22+/m0/s1 | StdInChIKey_Ref = | StdInChIKey = ZQHYKVKNPWDQSL-KNXBSLHKSA-N | synonyms = Fenazocina, Phenazocinum, DEA No. 9715 Phenazocine (brand names Prinadol, Narphen) is an opioid analgesic drug, which is related to pentazocine and has a similar profile of effects.

Effects of phenazocine include analgesia and euphoria, also may include dysphoria and hallucinations at high doses, most likely due to action at κ-opioid and σ receptors. Phenazocine appears to be a much stronger analgesic with fewer side effects than pentazocine, probably due to a more favorable μ/κ binding ratio. Phenazocine is a much more potent analgesic than pentazocine and other drugs in the benzomorphan series, most probably due to the presence of an N-phenethyl substitution, which is known to boost μ-opioid activity in many classes of opioid analgesics. Also, it does not cause spasm of the sphincter of Oddi, making it more suitable than morphine for the treatment of biliary or pancreatic pain.

Regarding the two enantiomers of phenazocine, (R)-phenazocine has twenty times the potency of morphine as an analgesic, while (S)-phenazocine has about four times the potency of morphine.

History

Phenazocine was invented in the 1950s. It was one of a number of benzomorphan opioids (including pentazocine, dezocine, and cyclazocine) developed in the search for non-addictive strong analgesics.

Phenazocine was once widely used, and was mainly supplied as 5 mg tablets of the hydrobromide salt for sublingual use (Narphen, Prinadol and other names), but its use was discontinued in the United Kingdom in 2001.

Phenazocine was briefly used in the United States but fell out of favor; it remains a Schedule II substance under the Comprehensive Drug Abuse Control & Prevention Act (Controlled Substances Act) of 1970 (CSA) but is not manufactured. The DEA ACSCN for phenazocine is 9715 and its 2013 annual manufacturing quota was 6 grams.

References

References

  1. Anvisa. (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial". [[Diário Oficial da União]].
  2. "Iso-benzmorphan derivatives".
  3. (February 1964). "Some Narcotic Antagonists in the Benzomorphan Series". Journal of Pharmacology and Experimental Therapeutics.
  4. (November 1976). "The opiate receptor: a model explaining structure-activity relationships of opiate agonists and antagonists". Proceedings of the National Academy of Sciences USA.
  5. Hopton D.. (January 1971). "Double-blind clinical trial of the analgesic effects of phenazocine hydrobromide (Narphen) compared with morphine sulphate in patients with acute abdominal pain". Gut.
  6. (August 1959). "Identification of Phenazocine, a Potent New Analgesic". Nature.
  7. Textbook of Pharmacology - Page 117
  8. Clarke EG. (August 8, 1959). "Identification of Phenazocine, a Potent New Analgesic". Nature.
  9. Eckenhoff JE. (May–June 1959). "Phenazocine, a new benzomorphan narcotic analgesic". Anesthesiology.
  10. (February 2001). "Monthly Release Terming and Coding Newsletter". NHS Information Authority.
  11. "Quotas - 2013". Drug Enforcement Agency, U.S. Department of Justice.

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benzomorphanshallucinogenic-kappa-opioid-receptor-agonistsmu-opioid-receptor-agonistshydroxyarenessynthetic-opioids