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

Clinical data
ATC code	None
Identifiers
IUPAC name 4-(Dimethylamino)-4-(4-methylphenyl)cyclohexan-1-one
CAS Number	65619-06-9
PubChem CID	12595643
ChemSpider	15036994
ChEMBL	ChEMBL341983
CompTox Dashboard (EPA)	DTXSID30503812
Chemical and physical data
Formula	C15H21NO
Molar mass	231.339 g·mol
3D model (JSmol)	Interactive image
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 (sometimes known as dimetamine) is a opioid 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 para-methyl group is replaced by a halogen being slightly weaker. Derivatives where the ketone group has been reacted with a Grignard reagent to add a phenethyl side chain are several hundred times stronger (as is seen in the compound BDPC).

Legal Status

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.

See also

• 3-HO-PCP
• 4-Keto-PCP
• Tramadol

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.

• Drugs not assigned an ATC code
• Arylcyclohexylamines
• Dimethylamino compounds
• Mu-opioid receptor agonists
• Synthetic opioids