Draft:Aminopentamide

Aminopentamide
Clinical data
Other names	Dimevamide, Centrine.
Identifiers
	IUPAC name 4-(dimethylamino)-2,2-diphenylpentanamide;
PubChem CID	22565;
ChemSpider	21159;
Chemical and physical data
Formula	C19H24N2O
Molar mass	296.414 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(CC(C1=CC=CC=C1)(C2=CC=CC=C2)C(=O)N)N(C)C;
	InChI 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;

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

Synthesis:^[1]

Abs config:^[2] Cryst:^[3] Pharmacol:^[4] (ord, uv):^[5]

References

^ Moffett, Robert Bruce; Aspergren, Brooke D. (1957). "Antispasmodics. X. α,α-Diphenyl-γ-amino Amides1". Journal of the American Chemical Society. 79 (16): 4451–4457. doi:10.1021/ja01573a056.
^ 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.
^ Colleter, J.C. et al, Bull. Soc. Pharm. Bordeaux, 1961, 100, 87 (cryst struct)
^ Yusuf, S.M. et al, Arch. Intern. Pharmacodyn., 1964, 152, 198 (pharmacol)
^ Crabbe, P. et al, Bull. Soc. Chim. Fr., 1965, 2855 (ord, uv)

[1] Moffett, Robert Bruce; Aspergren, Brooke D. (1957). "Antispasmodics. X. α,α-Diphenyl-γ-amino Amides1". Journal of the American Chemical Society. 79 (16): 4451–4457. doi:10.1021/ja01573a056.

[2] 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.

[3] Colleter, J.C. et al, Bull. Soc. Pharm. Bordeaux, 1961, 100, 87 (cryst struct)

[4] Yusuf, S.M. et al, Arch. Intern. Pharmacodyn., 1964, 152, 198 (pharmacol)

[5] Crabbe, P. et al, Bull. Soc. Chim. Fr., 1965, 2855 (ord, uv)

[1]

[2]

[3]

[4]

[5]

v t e Urologicals, including antispasmodics (G04B)
Acidifiers	Ammonium chloride Calcium chloride
Urinary antispasmodics (primarily antimuscarinics)	Darifenacin Desfesoterodine Emepronium Fesoterodine Flavoxate Imidafenacin Meladrazine Mirabegron Oxybutynin Propiverine Solifenacin Terodiline Tolterodine Trospium chloride Vibegron
Other urologicals	Urea analogues: Acetohydroxamic acid Salicylhydroxamic acid Other: Collagen Dapoxetine Dimethyl sulfoxide Magnesium hydroxide Pentosan polysulfate Phenazopyridine Phenyl salicylate Succinimide Tiopronin

v t e Irritable bowel syndrome (IBS)
Management	Low-FODMAP diet Gluten-free diet Soluble fiber Laxatives Antispasmodics Psychotherapy Tricyclic antidepressants SSRIs Probiotics Eluxadoline
Related topics	Gut–brain axis Hypothalamic–pituitary–adrenal axis Sympathetic nervous system

See also

References