Aminopentamide

Last updated

Aminopentamide
Aminopentamide.svg
Clinical data
Other namesDimevamide, Centrine.
Identifiers
  • 4-(dimethylamino)-2,2-diphenylpentanamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.000.436 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C19H24N2O
Molar mass 296.414 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.

Contents

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

References

  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. 1 2 3 4 5 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. 1 2 3 4 Dodman N (August 8, 2015). "Aminopentamide (Centrine) for Dogs and Cats". PetPlace.com. Retrieved 2025-06-02.
  5. 1 2 3 4 5 Forney B (12 July 2022). "Aminopentamide Hydrogen Sulfate for Dogs and Cats". Wedgewood Pharmacy. Retrieved 2025-06-02.
  6. 1 2 3 4 "Centrine Tablets". Drugs.com. Retrieved 2025-06-02.
  7. 1 2 3 4 "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 (inactive 1 July 2025).{{cite journal}}: CS1 maint: DOI inactive as of July 2025 (link)
  9. 1 2 3 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 Pharmaciaand Upjohn Co
  14. ↑ US 3896221,Christie GJ, Buckwalter FH,"Anesthetic composition",published 1973-02-28,issued 1975-07-22
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.