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Phenazocine

Opioid analgesic From Wikipedia, the free encyclopedia

Phenazocine (brand names Prinadol, Narphen) is an opioid analgesic drug, which is related to pentazocine and has a similar profile of effects.[2]

Other namesFenazocina, Phenazocinum, DEA No. 9715
Routes of
administrationOral
Drug classκ-Opioid receptor agonist; μ-Opioid receptor agonist–antagonist; Opioid analgesic; Hallucinogen
ATC code
Quick facts Clinical data, Other names ...
Phenazocine
Clinical data
Other namesFenazocina, Phenazocinum, DEA No. 9715
Routes of
administration		Oral
Drug classκ-Opioid receptor agonist; μ-Opioid receptor agonist–antagonist; Opioid analgesic; Hallucinogen
ATC code
Legal status
Legal status
Identifiers
  • (2R,6R,11R)-6,11-Dimethyl-3-(2-phenylethyl)-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocin-8-ol
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.004.397 Edit this at Wikidata
Chemical and physical data
FormulaC22H27NO
Molar mass321.464 g·mol−1
3D model (JSmol)
  • C[C@H]1[C@H]2Cc3ccc(cc3[C@@]1(CCN2CCc4ccccc4)C)O
  • InChI=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 X markN
  • Key:ZQHYKVKNPWDQSL-KNXBSLHKSA-N X markN
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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.[3] 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.[4] 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.[5]

Regarding the two enantiomers of phenazocine, (R)-phenazocine[clarification needed] has twenty times the potency of morphine as an analgesic,[6] while (S)-phenazocine has about four times the potency of morphine.[7][full citation needed]

History

Phenazocine was invented in the 1950s.[8][9] 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.[10]

Phenazocine was briefly used in the United States but fell out of favor;[citation needed] 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.[11]

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