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Aminopentamide

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Aminopentamide
Clinical data
Other namesDimevamide, Centrine.
Identifiers
  • 4-(dimethylamino)-2,2-diphenylpentanamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
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 and antidiarrheal drug and also a bird and rodent repellent.[1][2] It is structurally related to Darifenacin.

It is used to treat vomiting, diarrhea, gastrointestinal pain and spasms in cats and dogs.[3] The commercially available drug named Centrine contains aminopentamide bisulfate.[3]

Medical uses

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Aminopentamide is used to alleviate vomiting and diarrhea by reducing gastric motility, decreasing gastric acid secretion, and lowering gastric acidity.[4][5][6] It is also effective against visceral spasms and pylorospasm in dogs and cats due to its antispasmodic properties.[7][4]

Side effects

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Aminopentamide may cause mild anticholinergic side effects such as dry mouth or urinary retention.[5][6] At very high doses, it can produce mydriasis and hyposalivation, though these effects are less pronounced than with atropine.[8]

Pharmacology

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Aminopentamide is a synthetic anticholinergic agent that acts as a nonselective muscarinic receptor antagonist, primarily targeting smooth muscle in the gastrointestinal tract.[7][5] It reduces gastric motility, decreases gastric acid secretion, and lowers gastric acidity.[4][5][6] Compared to atropine, aminopentamide demonstrates stronger and longer-lasting suppression of colonic contraction amplitude and tone while causing fewer systemic side effects like mydriasis or excessive salivary inhibition.[7][5][6] It acts by blocking cholinergic transmission at parasympathetic nerve endings.[7][4] Aminopentamide has half the potency of atropine and one-fifth the potency of papaverine. It has similar bioavailability when taken orally, intramuscularly, or intravenously.[9] It is more suitable for decreasing the activity of the colon than atropine or banthine, being more effective and longer-lasting.[9]

Chemistry

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The synthesis is the same as for methadone except for the last step where the nitrile called 2,2-diphenyl-4-dimethylaminovaleronitrile[10] is partially hydrolyzed into an amide instead of being converted to a ketone.[11]

History

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Aminopentamide was discovered by Bristol Laboratories and was patented in 1953.[12][13][3] Its pharmacological activity was reported on a year later by Hoekstra et al.[9][3]

Another patent from 1975 claims an anesthetic mixture for cats that contains aminopentamide along with ketamine, which supposedly alleviates some of the side-effects of ketamine.[14][3]

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. ^ Papich MG (2016). "Aminopentamide". Saunders Handbook of Veterinary Drugs. Elsevier. p. 28. doi:10.1016/b978-0-323-24485-5.00076-0. ISBN 978-0-323-24485-5. Retrieved 2025-06-01.
  3. ^ a b c d e Kaduk JA, Gindhart AM, Gates-Rector S, Blanton TN (2022-09-09). "Crystal structure of aminopentamide hydrogen sulfate, (C19H25N2O)(HSO4)" (PDF). Powder Diffraction. 37 (4). Cambridge University Press (CUP): 200–205. Bibcode:2022PDiff..37..200K. doi:10.1017/s0885715622000343. ISSN 0885-7156. Retrieved 2025-06-01.
  4. ^ a b c d Dodman N (August 8, 2015). "Aminopentamide (Centrine) for Dogs and Cats". PetPlace.com. Retrieved 2025-06-02.
  5. ^ a b c d e Forney B (12 July 2022). "Aminopentamide Hydrogen Sulfate for Dogs and Cats". Wedgewood Pharmacy. Wedgewood Pharmacy. Retrieved 2025-06-02.
  6. ^ a b c d "Centrine Tablets". Drugs.com. Retrieved 2025-06-02.
  7. ^ a b c d "Aminopentamide". Inxight Drugs. National Center for Advancing Translational Sciences (NCATS), U.S. Department of Health & Human Services. Retrieved 2025-06-02.
  8. ^ Hoekstra WG, Jackson EM, Ballard RW (1954). "Aminopentamide, a new antispasmodic agent". Journal of the American Medical Association. 156 (11): 1019–1022. doi:10.1001/jama.1954.02950290021005.
  9. ^ a b c Hoekstra J, Tisch D, Rakieten N, Dickison H (Jan 1954). "The Pharmacological Activity of Dl-Alpha, Alpha-Diphenyl, Gamma-Dimethylaminovaleramide (Centrine)". The Journal of Pharmacology and Experimental Therapeutics. 110 (1). Elsevier BV: 55–67. doi:10.1016/s0022-3565(25)04464-7. ISSN 0022-3565. PMID 13118479.
  10. ^ Golzadeh R, Mahkam M, Rezaii E, Nazmi Miardan L (December 22, 2021). "Green synthesis of methadone in eutectic solvent". Main Group Chemistry. 20 (4): 463–474. doi:10.3233/MGC-210058. ISSN 1024-1221. Retrieved June 1, 2025.
  11. ^ Moffett RB, Aspergren BD (August 1957). "Antispasmodics. X. α,α-Diphenyl-γ-amino Amides 1". Journal of the American Chemical Society. 79 (16): 4451–4457. Bibcode:1957JAChS..79.4451M. doi:10.1021/ja01573a056.
  12. ^ US 2647926, Speeter ME, "Diphenyl-dimethyl-aminovaleramide", published 21 July 1955, issued 4 August 1953, assigned to Bristol Laboratories Inc 
  13. ^ US 3072722, Aspergren BD, Moffett RB, Speeter ME, "Preparation of amides of 4-tertiary amino-lower 4-alkylbutyric acids", published 21 July 1955, issued 8 January 1963, assigned to Pharmacia and Upjohn Co 
  14. ^ US 3896221, Christie GJ, Buckwalter FH, "Anesthetic composition", published 1973-02-28, issued 1975-07-22 
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