Dimethylaminopivalophenone

Dimethylaminopivalophenone

Systematic (IUPAC) name
3-(dimethylamino)-2,2-dimethyl-1-phenylpropan-1-one
Identifiers
CAS Number	15451-29-3
PubChem	CID 84922
ChemSpider	76610
Chemical data
Formula	C13H19NO
Molar mass	205.30 g·mol^−1
SMILES CN(CC(C(=O)C1=CC=CC=C1)(C)C)C
InChI InChI=1S/C13H19NO/c1-13(2,10-14(3)4)12(15)11-8-6-5-7-9-11/h5-9H,10H2,1-4H3 Key:WKJYCZMXCFRIEO-UHFFFAOYSA-N

Dimethylaminopivalophenone^[1][2] is an opioid analgesic.^[3] with a potency ½ that of morphine. It was initially discovered by Russian scientists in 1954 and subsequently rediscovered in the US in 1969.^[4] Its LD₅₀ in mice is 83 mg/kg.^[5]

See also

• Tapentadol
• List of opioids
• Opioid#Table of non-morphinan opioids

References

1. James H. Brewster, Ernest L. Eliel (2011). "Carbon-Carbon Alkylations with Amines and Ammonium Salts". Organic Reactions 7 (3): 99–197. doi:10.1002/0471264180.or007.03.
2. Edward F. Kleinman (April 2011). "Dimethyl(methylene)ammonium Iodide". e-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rd346.
3. Helmut Buschmann, Wolfgang Strassburger, Elmar Friderichs (24 January 2002). "Patent US 20020010178 - 1-phenyl-3-dimethylaminopropane compounds with a pharmacological effect". Retrieved 2 October 2015.
4. Manmohan S. Atwal, Ludwig Bauer, S. N. Dixit, J. E. Gearien, M. Magahy, R. Morris, C. Pokorny (November 1969). "Analgetics. II. Relationship between structure and activity of some beta-amino ketones.". Journal of Medicinal Chemistry 12 (6): 994–997. doi:10.1021/jm00306a006. PMID 5351480.
5. "2,2-dimethyl-3-(dimethylamino)-Propiophenone". ChemIDplus. Retrieved 2 October 2015.