|CompTox Dashboard (EPA)|
|Chemical and physical data|
|Molar mass||231.339 g·mol−1|
|3D model (JSmol)|
4-Dimethylamino-4-(p-tolyl)cyclohexanone (sometimes known as dimetamine) is a narcotic analgesic with an arylcyclohexylamine chemical structure. It was developed by Daniel Lednicer at Upjohn in the 1970s. It has around the same analgesic potency as morphine, with analogues where the p-methyl group is replaced by chlorine or bromine being slightly weaker. However derivatives where the ketone group has been reacted with a Grignard reagent to add a phenethyl substitution are several hundred times stronger, and in this series it is the bromo compound BDPC that is the most potent.
4-Dimethylamino-4-(p-tolyl)cyclohexanone is specifically listed as an illegal drug in Latvia. It is also covered by drug analogue laws in various jurisdictions as a generic arylcyclohexylamine derivative.
- This is ambiguous, as Dimetamine is also the name of an unrelated alkaloid, as well as a trade name for propylhexedrine.
- US 4366172, Lednicer D, "4-Amino-cyclohexanols, their pharmaceutical compositions and methods of use", issued 1982-12-28, assigned to Upjohn Company
- Lednicer D, VonVoigtlander PF, Emmert DE (April 1980). "4-Amino-4-arylcyclohexanones and their derivatives, a novel class of analgesics. 1. Modification of the aryl ring". Journal of Medicinal Chemistry. 23 (4): 424–30. doi:10.1021/jm00178a014. PMID 7381841.
- Lednicer D, VonVoigtlander PF, Emmert DE (April 1981). "4-amino-4-arylcyclohexanones and their derivatives: a novel class of analgesics. 2. Modification of the carbonyl function". Journal of Medicinal Chemistry. 24 (4): 404–8. doi:10.1021/jm00136a010. PMID 7265128.
- Lednicer D, Von Voigtlander PF, Emmert DE (March 1981). "4-aryl-4-aminocyclohexanones and their derivatives, a novel class of analgesics. 3. m-Hydroxyphenyl derivates". Journal of Medicinal Chemistry. 24 (3): 341–6. doi:10.1021/jm00135a019. PMID 7265120.
- "Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem". Archived from the original on 2016-03-04. Retrieved 2019-11-15.