Compound: ETHOHEPTAZINE
SMILES: O=C(OCC)C1(c2ccccc2)CCN(C)CCC1
InChIKey: WGJHHMKQBWSQIY-UHFFFAOYSA-N
Synonyms: ETHOHEPTAZINE, Aethoheptazin, 77-15-6, ethyl 1-methyl-4-phenylazepane-4-carboxylate, Ethyl heptazine, Zactane, Ethoheptazinum, Etoheptazina, WY 401, 4-Carbethoxy-1-methyl-4-phenylazacycloheptane, 1-Methyl-4-carbethoxy-4-phenylhexamethylenimine, 4-Carbethoxy-1-methyl-4-phenylhexamethylenimine, 1-Methyl-4-carbethoxy-4-phenylhexamethyleneimine, 3A4G3A848U, 1H-Azepine-4-carboxylic acid, hexahydro-1-methyl-4-phenyl-, ethyl ester, Ethyl hexahydro-1-methyl-4-phenyl-azepine-4-carboxylate, Hexahydro-1-methyl-4-phenyl-4-azepinecarboxylic acid ethyl ester, Azepine-4-carboxylic acid, hexahydro-1-methyl-4-phenyl-, ethyl ester, DTXSID7023017, RefChem:592707, DTXCID403017, 201-007-3, Aethoheptazin;Ethyl heptazine;Wy 401, Ethoheptazinum [INN-Latin], Etoheptazina [INN-Spanish], HSDB 3326, NCGC00183870-01, EINECS 201-007-3, Ethoheptazine [INN:BAN], BRN 0088192, UNII-3A4G3A848U, ETHOHEPTAZINE [MI], ETHOHEPTAZINE [INN], ETHOHEPTAZINE [HSDB], SCHEMBL24581, ETHOHEPTAZINE [VANDF], 4-22-00-01044 (Beilstein Handbook Reference), ETHOHEPTAZINE [WHO-DD], CHEMBL170797, CHEBI:135074, EBC-26358, AKOS016010413, DB08988, Ethyl 1-methyl-4-phenyl-4-azepanecarboxylate #, EN300-18562833, Q5404408, Ethyl hexahydro-1-methyl-4-phenyl-1H-azepine-4-carboxylate, 4-ETHOXYCARBONYL-1-METHYL-4-PHENYL-HEXAHYDRO-1H-AZEPINE
Theoretical properties:
molecular_formula: C16H23NO2
molecular_weight: 261.36 g/mol
exact_mass: 261.172878976 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 4
heavy_atom_count: 19
topological_polar_surface_area: 29.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: LIQUID
color: LIQUID
boiling_point: 127-129 °C/0.5 MM HG
melting_point: 122-124
density: 1.038 @ 26 °C/4 °C
Descriptions:
pubchem: Ethoheptazine is a member of azepanes.
chembl: ETHOHEPTAZINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: 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.