Chemistry:Aminopentamide

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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

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

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

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

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

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

  • Vamicamide

References

  1. ↑ The Dictionary of Drugs: Chemical Data: Chemical Data, Bibliographies. Springer. 14 November 2014. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ. 
  2. ↑ "Aminopentamide". Saunders Handbook of Veterinary Drugs. Elsevier. 2016. pp. 28. doi:10.1016/b978-0-323-24485-5.00076-0. ISBN 978-0-323-24485-5. https://linkinghub.elsevier.com/retrieve/pii/B9780323244855000760. Retrieved 2025-06-01. 
  3. ↑ 3.0 3.1 3.2 3.3 3.4 "Crystal structure of aminopentamide hydrogen sulfate, (C19H25N2O)(HSO4)". Powder Diffraction (Cambridge University Press (CUP)) 37 (4): 200–205. 2022-09-09. doi:10.1017/s0885715622000343. ISSN 0885-7156. Bibcode: 2022PDiff..37..200K. https://www.cambridge.org/core/services/aop-cambridge-core/content/view/905B5AD3BF6DC16F77DD21ECF58DE062/S0885715622000343a.pdf/div-class-title-crystal-structure-of-aminopentamide-hydrogen-sulfate-c-span-class-sub-19-span-h-span-class-sub-25-span-n-span-class-sub-2-span-o-hso-span-class-sub-4-span-div.pdf. Retrieved 2025-06-01. 
  4. ↑ 4.0 4.1 4.2 4.3 "Aminopentamide (Centrine) for Dogs and Cats". PetPlace.com. August 8, 2015. https://www.petplace.com/article/drug-library/drug-library/library/aminopentamide-centrine-for-dogs-and-cats. 
  5. ↑ 5.0 5.1 5.2 5.3 5.4 "Aminopentamide Hydrogen Sulfate for Dogs and Cats". 12 July 2022. https://www.wedgewood.com/medications/aminopentamide-hydrogen-sulfate/. 
  6. ↑ 6.0 6.1 6.2 6.3 "Centrine Tablets". Drugs.com. https://www.drugs.com/vet/centrine-tablets.html. 
  7. ↑ 7.0 7.1 7.2 7.3 "Aminopentamide". National Center for Advancing Translational Sciences (NCATS), U.S. Department of Health & Human Services. https://drugs.ncats.io/drug/IP1B47L61M. 
  8. ↑ "Aminopentamide, a new antispasmodic agent". Journal of the American Medical Association 156 (11): 1019–1022. 1954. doi:10.1001/jama.1954.02950290021005. 
  9. ↑ 9.0 9.1 9.2 "The Pharmacological Activity of Dl-Alpha, Alpha-Diphenyl, Gamma-Dimethylaminovaleramide (Centrine)". The Journal of Pharmacology and Experimental Therapeutics (Elsevier BV) 110 (1): 55–67. Jan 1954. doi:10.1016/s0022-3565(25)04464-7. ISSN 0022-3565. PMID 13118479. 
  10. ↑ "Green synthesis of methadone in eutectic solvent". Main Group Chemistry 20 (4): 463–474. December 22, 2021. doi:10.3233/MGC-210058. ISSN 1024-1221. https://journals.sagepub.com/doi/10.3233/MGC-210058. Retrieved June 1, 2025. 
  11. ↑ "Antispasmodics. X. α,α-Diphenyl-γ-amino Amides 1". Journal of the American Chemical Society 79 (16): 4451–4457. August 1957. doi:10.1021/ja01573a056. Bibcode: 1957JAChS..79.4451M. 
  12. ↑ Speeter ME, "Diphenyl-dimethyl-aminovaleramide", US patent 2647926, published 21 July 1955, issued 4 August 1953, assigned to Bristol Laboratories Inc
  13. ↑ Aspergren BD, Moffett RB, Speeter ME, "Preparation of amides of 4-tertiary amino-lower 4-alkylbutyric acids", US patent 3072722, published 21 July 1955, issued 8 January 1963, assigned to Pharmaciaand Upjohn Co
  14. ↑ Christie GJ, Buckwalter FH, "Anesthetic composition", US patent 3896221, published 1973-02-28, issued 1975-07-22



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