4-Dimethylamino-4-(p-tolyl)cyclohexanone

4-Dimethylamino-4-(p-tolyl)cyclohexanone (sometimes known as dimetamine)[1] is a narcotic analgesic with an arylcyclohexylamine chemical structure. It was developed by Daniel Lednicer at Upjohn in the 1970s.[2] 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.[3][4][5]

4-Dimethylamino-4-(p-tolyl)cyclohexanone
Clinical data
ATC code
  • None
Identifiers
IUPAC name
  • 4-(Dimethylamino)-4-(4-methylphenyl)cyclohexan-1-one
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H21NO
Molar mass231.339 g·mol−1
3D model (JSmol)
SMILES
  • CC1=CC=C(C=C1)C2(CCC(=O)CC2)N(C)C
InChI
  • InChI=1S/C15H21NO/c1-12-4-6-13(7-5-12)15(16(2)3)10-8-14(17)9-11-15/h4-7H,8-11H2,1-3H3
  • Key:VCEODKLEIJWHMI-UHFFFAOYSA-N

4-Dimethylamino-4-(p-tolyl)cyclohexanone is specifically listed as an illegal drug in Latvia.[6] It is also covered by drug analogue laws in various jurisdictions as a generic arylcyclohexylamine derivative.

See also

References
  1. This is ambiguous, as Dimetamine is also the name of an unrelated alkaloid, as well as a trade name for propylhexedrine.
  2. US 4366172, Lednicer D, "4-Amino-cyclohexanols, their pharmaceutical compositions and methods of use", issued 1982-12-28, assigned to Upjohn Company
  3. 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.
  4. 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.
  5. 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.
  6. "Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem". Archived from the original on 2016-03-04. Retrieved 2019-11-15.
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