Phenazocine

Phenazocine
Clinical data
Synonyms	Phenazocine, Prinadol, Narphen
Identifiers
	IUPAC name 1,2,3,4,5,6-hexahydro-6,11-dimethyl-3- (2-phenylethyl)-2,6-Methano-3-benzazocin-8-ol;
CAS Number	127-35-5;
PubChem CID	14707;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C22H27NO
Molar mass	321.46 g/mol

Phenazocine (Prinadol, Narphen) is an opioid analgesic, invented in the 1950s,^[1]^[2] which is related to pentazocine and has a similar profile of effects that include analgesic action and euphoria, but may produce dysphoria and hallucinations at high doses, most likely due to action at κ-opioid and σ receptors.^[3] However phenazocine appears to be a much stronger analgesic and with less side effects than pentazocine, probably reflecting a more favourable μ/κ binding ratio. Phenazocine used to be widely used in medicine, mainly supplied as 5mg tablets of the hydrobromide salt, but was discontinued in 2001 and is now no longer used.[1]

Phenazocine is much more potent as an 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] 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.^[5]

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References

↑ Clarke EGC. Identification of Phenazocine, a Potent New Analgesic. Nature. 1959; 184: 451.
↑ Eckenhoff JE. Phenazocine, a new benzomorphan narcotic analgesic. Anesthesiology. 1959 May-Jun;20(3):355-8.
↑ Harris LS, Pierson AK. Some Narcotic Antagonists in the Benzomorphan Series. Journal of Pharmacology and Experimental Therapeutics. 1964 Feb;143:141-8.
↑ Feinberg AP, Creese I, Snyder SH. The opiate receptor: a model explaining structure-activity relationships of opiate agonists and antagonists. Proceedings of the National Academy of Sciences U S A. 1976 Nov;73(11):4215-9.
↑ Hopton D. Double-blind clinical trial of the analgesic effects of phenazocine hydrobromide (Narphen) compared with morphine sulphate in patients with acute abdominal pain. Gut. 1971 Jan;12(1):51-4.

Template:Opioids

[1] Clarke EGC. Identification of Phenazocine, a Potent New Analgesic. Nature. 1959; 184: 451.

[2] Eckenhoff JE. Phenazocine, a new benzomorphan narcotic analgesic. Anesthesiology. 1959 May-Jun;20(3):355-8.

[3] Harris LS, Pierson AK. Some Narcotic Antagonists in the Benzomorphan Series. Journal of Pharmacology and Experimental Therapeutics. 1964 Feb;143:141-8.

[4] Feinberg AP, Creese I, Snyder SH. The opiate receptor: a model explaining structure-activity relationships of opiate agonists and antagonists. Proceedings of the National Academy of Sciences U S A. 1976 Nov;73(11):4215-9.

[5] Hopton D. Double-blind clinical trial of the analgesic effects of phenazocine hydrobromide (Narphen) compared with morphine sulphate in patients with acute abdominal pain. Gut. 1971 Jan;12(1):51-4.

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Phenazocine

References

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