Dimethylaminopivalophenone

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Dimethylaminopivalophenone
3-(dimethylamino)-2,2-dimethyl-1-phenylpropan-1-one.svg
Identifiers
  • 3-(dimethylamino)-2,2-dimethyl-1-phenylpropan-1-one
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H19NO
Molar mass205.301 g·mol−1
3D model (JSmol)
  • CN(CC(C(=O)C1=CC=CC=C1)(C)C)C
  • 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.

See also[edit]

References[edit]

  1. ^ Brewster JH, Eliel EL (2011). "Carbon-Carbon Alkylations with Amines and Ammonium Salts". Organic Reactions. 7 (3): 99–197. doi:10.1002/0471264180.or007.03.
  2. ^ Kleinman EF (April 2011). "Dimethyl(methylene)ammonium Iodide". Encyclopedia of Reagents for Organic Synthesis. E-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rd346. ISBN 978-0471936237.
  3. ^ Buschmann H, Strassburger W, Friderichs E (24 January 2002). "Patent US 20020010178 - 1-phenyl-3-dimethylaminopropane compounds with a pharmacological effect". Retrieved 2 October 2015.
  4. ^ Atwal MS, Bauer L, Dixit SN, Gearien JE, Megahy M, Morris R, Pokorny C (November 1969). "Analgetics. II. Relationship between structure and activity of some beta-amino ketones". Journal of Medicinal Chemistry. 12 (6): 994–7. doi:10.1021/jm00306a006. PMID 5351480.
  5. ^ "2,2-dimethyl-3-(dimethylamino)-Propiophenone". ChemIDplus. Retrieved 2 October 2015.