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Draft:Aminopentamide

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Aminopentamide
Clinical data
Other namesDimevamide, Centrine.
Identifiers
  • 4-(dimethylamino)-2,2-diphenylpentanamide
PubChem CID
ChemSpider
Chemical and physical data
FormulaC19H24N2O
Molar mass296.414 g·mol−1
3D model (JSmol)
  • CC(CC(C1=CC=CC=C1)(C2=CC=CC=C2)C(=O)N)N(C)C
  • InChI=1S/C19H24N2O/c1-15(21(2)3)14-19(18(20)22,16-10-6-4-7-11-16)17-12-8-5-9-13-17/h4-13,15H,14H2,1-3H3,(H2,20,22)
  • Key:NARHAGIVSFTMIG-UHFFFAOYSA-N

Aminopentamide is an anticholinergic antispasmodic drug; also a bird and rodent repellent.[1] Part of the structure clearly is similar to Darifenacin. Functionalizing the primary amide would be consistent with narcotic analgesic potency, as for example moramide.

The synthesis is the same as for methadone except for the last step the nitrile is partly hydrolyzed into an amide instead of reacted to form a ketone.[2]

Abs config:[3] Cryst:[4] Pharmacol:[5] (ord, uv):[6]

See also

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References

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  1. ^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Bibliographies. Springer. ISBN 978-1-4757-2085-3.
  2. ^ Moffett, R. B., Aspergren, B. D. (August 1957). "Antispasmodics. X. α,α-Diphenyl-γ-amino Amides 1". Journal of the American Chemical Society. 79 (16): 4451–4457. doi:10.1021/ja01573a056.
  3. ^ Beckett, A. H.; Casy, A. F. (1957). "600. Configurational studies in synthetic analgesics. Part III. The configuration of (–)-phenadoxone". J. Chem. Soc. 0 (0): 3076–3079. doi:10.1039/JR9570003076.
  4. ^ Colleter, J.C. et al, Bull. Soc. Pharm. Bordeaux, 1961, 100, 87 (cryst struct)
  5. ^ Yusuf, S.M. et al, Arch. Intern. Pharmacodyn., 1964, 152, 198 (pharmacol)
  6. ^ Crabbe, P. et al, Bull. Soc. Chim. Fr., 1965, 2855 (ord, uv)