Dimethylaminopivalophenone

Dimethylaminopivalophenone
Identifiers
	IUPAC name 3-(dimethylamino)-2,2-dimethyl-1-phenylpropan-1-one;
CAS Number	15451-29-3;
PubChem CID	84922;
ChemSpider	76610;
CompTox Dashboard (EPA)	DTXSID90165652 ;
Chemical and physical data
Formula	C13H19NO
Molar mass	205.301 g·mol−1
3D model (JSmol)	Interactive image;
	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] It has never been marketed commercially, likely due to its low potency and lack of benefits compared to existing agents.

References

^ 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.
^ Edward F. Kleinman (April 2011). Dimethyl(methylene)ammonium Iodide. doi:10.1002/047084289X.rd346. ISBN 978-0471936237. {{cite book}}: |journal= ignored (help)CS1 maint: year (link)
^ 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.
^ 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.
^ "2,2-dimethyl-3-(dimethylamino)-Propiophenone". ChemIDplus. Retrieved 2 October 2015.

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[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. doi:10.1002/047084289X.rd346. ISBN 978-0471936237. {{cite book}}: |journal= ignored (help)CS1 maint: year (link)

[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.

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See also

References