Ethoheptazine

Ethoheptazine[1] (trade name Zactane) is an opioid analgesic from the phenazepane family. It was invented in the 1950s[2] and is a ring expanded analogue of pethidine.[3]

Ethoheptazine
Clinical data
Trade namesEquagesic
Other namesZactane
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • US: Schedule IV (Some preparations)
Identifiers
IUPAC name
  • Ethyl 1-methyl-4-phenylazepane-4-carboxylate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.917
Chemical and physical data
FormulaC16H23NO2
Molar mass261.365 g·mol−1
3D model (JSmol)
SMILES
  • O=C(OCC)C2(c1ccccc1)CCN(C)CCC2
InChI
  • InChI=1S/C16H23NO2/c1-3-19-15(18)16(14-8-5-4-6-9-14)10-7-12-17(2)13-11-16/h4-6,8-9H,3,7,10-13H2,1-2H3 Y
  • Key:WGJHHMKQBWSQIY-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Ethoheptazine produces similar effects to other opioids, including analgesia, sedation, dizziness and nausea.[4] It was sold by itself as Zactane, and is still available as a combination product with acetylsalicylic acid and meprobamate as Equagesic, which is used for the treatment of conditions where both pain and anxiety are present.[5] It was also investigated for use as an antitussive.[6]

It is no longer prescribed, as it is no longer FDA approved, and not available for United States' Pharmacy Processing. Revocation of FDA Approved Medications Status stems from a combination of efficacy vs. toxicity, and the more-varied and historically safer Benzodiazepines Class. Only reversal of the FDA's decision, allows removing the drug from the CSD. Ethoheptazine is not listed as a controlled substance under the Controlled Substances Act, 1970 in the United States.[7] The controlled status (Schedule IV) of Equagesic was due to the meprobamate content.[8][7] Regulation elsewhere varies.

References
  1. ES 310184, "Procedure for the preparation of a new derivative of pirazolidine-hexametilenimina with therapeutic properties."
  2. Batterman RC, Golbey M, Grossman AJ, Leifer P (October 1957). "Analgesic effectiveness of orally administered ethoheptazine in man". The American Journal of the Medical Sciences. 234 (4): 413–9. doi:10.1097/00000441-195710000-00004. PMID 13469802. S2CID 32299049.
  3. Diamond J, Bruce WF, Tyson FT (January 1964). "Synthesis and Properties of the Analgesic DL-α-1,3-dimethyl-4-phenyl-4-propionoxyazacycloheptane (Proheptazine)". Journal of Medicinal Chemistry. 7: 57–60. doi:10.1021/jm00331a013. PMID 14186026.
  4. Cinelli P, Zucchini M (March 1962). "[Current pharmaco-therapeutic possiblities in the treatment of pain. Experiments with ethoeptazine]". Minerva Medica (in Italian). 53: 637–42. PMID 13879557.
  5. Scheiner JJ, Richards DJ (September 1974). "Treatment of musculoskeletal pain and associated anxiety with an ethoheptazine-aspirin-meprobamate combination (equagesic): a controlled study". Current Therapeutic Research, Clinical and Experimental. 16 (9): 928–36. PMID 4214668.
  6. Overton DA, Batta SK (November 1979). "Investigation of narcotics and antitussives using drug discrimination techniques". The Journal of Pharmacology and Experimental Therapeutics. 211 (2): 401–8. PMC 8331839. PMID 41087.
  7. "Conversion Factors for Controlled Substances". Diversion Control Division. Drug Enforcement Agency, U.S. Department of Justice.
  8. PDR 1978, pp 1618


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