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Ethoheptazine

Clinical data
Trade names	Zactane, Equagesic
Other names	Zactane
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	77-15-6
PubChem CID	6469
DrugBank	DB08988
ChemSpider	6225
UNII	3A4G3A848U
ChEMBL	ChEMBL170797
CompTox Dashboard (EPA)	DTXSID7023017
ECHA InfoCard	100.000.917
Chemical and physical data
Formula	C16H23NO2
Molar mass	261.365 g·mol
3D model (JSmol)	Interactive image
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 Key:WGJHHMKQBWSQIY-UHFFFAOYSA-N
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Ethoheptazine (trade name Zactane) is an opioid analgesic from the phenazepane family. It was invented in the 1950s and is a ring expanded analogue of pethidine.

Ethoheptazine produces similar effects to other opioids, including analgesia, sedation, dizziness, and nausea. 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. It was also investigated for use as an antitussive.

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. The controlled status (Schedule IV) of Equagesic was due to the meprobamate content. 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). "". 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. Archived from the original on 2016-03-02. Retrieved 2016-02-27.
8. PDR 1978, pp 1618

• Drugs not assigned an ATC code
• Synthetic opioids
• Azepanes
• Ethyl esters
• Mu-opioid receptor agonists