Phenazocine

Overview

Phenazocine (brand names Prinadol, Narphen) is an opioid analgesic drug, which is related to pentazocine and has a similar profile of effects.[1] WP

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.[2][3][4] WP

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.[5][6] WP⚠ Part of this sentence could not be copied from the source. Open the source to read it in full.⚠ Wikipedia itself has flagged this text: clarification needed.

History

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.[5][7] WP

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.[8] WP

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.[9] WP⚠ Wikipedia itself has flagged this text: citation needed.

Chemistry

Formula

C22H27NO PC

CAS number

127-35-5 PC

Molar mass (g/mol)

321.5 PC

IUPAC name (computed by PubChem)

1,13-dimethyl-10-(2-phenylethyl)-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-4-ol PC

SMILES

CC1C2CC3=C(C1(CCN2CCC4=CC=CC=C4)C)C=C(C=C3)O PC

InChIKey

ZQHYKVKNPWDQSL-UHFFFAOYSA-N PC

PubChem CID

14707

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Other Iso-benzmorphan derivatives
2. Journal / agency Harris LS, Pierson AK. Some Narcotic Antagonists in the Benzomorphan Series. Journal of Pharmacology and Experimental Therapeutics. February 1964. doi:10.1016/S0022-3565(25)26704-0 · PMID 14163985
3. Journal / agency 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 USA. November 1976. doi:10.1073/pnas.73.11.4215 · PMID 186791 · PMC431391
4. Journal / agency 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. January 1971. doi:10.1136/gut.12.1.51 · PMID 4929685 · PMC1411461
5. Journal / agency Clarke, E. G. C. Identification of Phenazocine, a Potent New Analgesic. Nature. August 1959. doi:10.1038/184451a0 · PMID 13810504
6. Other Textbook of Pharmacology - Page 117
7. Journal / agency Eckenhoff JE. Phenazocine, a new benzomorphan narcotic analgesic. Anesthesiology. May–June 1959. doi:10.1097/00000542-195905000-00016 · PMID 13650222
8. Other Monthly Release Terming and Coding Newsletter. February 2001
9. Other Quotas - 2013

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.