Phenazocine

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Phenazocine
180px
Systematic (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
Clinical data
Routes of
administration		 Oral
Legal status
Legal status
  • UK: Class A, Withdrawn
Identifiers
CAS Number 127-35-5
ATC code N02AD02 (WHO)
PubChem CID 443405
Synonyms Fenazocina, Phenazocinum, DEA No. 9715
Chemical data
Formula C22H27NO
Molar mass 321.45588 g/mol[[Script error: No such module "String".]]
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Phenazocine (brandnames 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.[1]

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.[2]

Consequently phenazocine is some 4x the potency of morphine as an analgesic. 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.[3]

History

Phenazocine was invented in the 1950s. [4][5] 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 5mg tablets of the hydrobromide salt for sublingual use (Narphen, Prinadol and other names), but its use was discontinued in the United Kingdom in 2001.[6]

Phenazocine was briefly used in the United States but fell out of favour for the above-mentioned reasons; it remains a Schedule II substance under the Comprehensive Drug Abuse Control & Prevention Act (aka Controlled Substances Act) of 1970 (CSA) but is not manufactured; other Schedule II narcotics not in use in the United States include bezitramide and metopon.

References

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Opioids
See also: Opioids template
Opium & alkaloids thereof
Semi-synthetic opium
derivatives
Synthetic opioids
Pyrazolones
Cannabinoids
Anilides
Non-steroidal
anti-inflammatories
See also: NSAIDs template
Propionic acid class
Oxicam class
Acetic acid class
Anthranilic acid
(fenamate) class
Atypical, Adjuvant & Potentiators,
Metabolic agents and miscellaneous
sv:Fenazocin
  1. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
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  3. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  4. ↑ Clarke EG (August 8, 1959). "Identification of Phenazocine, a Potent New Analgesic". Nature. 184(Suppl 7) (184(Suppl 7)): 451. PMID 13810504. 
  5. ↑ Eckenhoff JE (May–June 1959). "Phenazocine, a new benzomorphan narcotic analgesic". Anesthesiology. 20 (3): 355–8. doi:10.1097/00000542-195905000-00016. PMID 13650222. 
  6. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
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