3638. Eptastigmine

Nomenclature

CAS number: 101246-68-8
(3aS,8aR)-1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-yl heptylcarbamic acid ester; N-demethyl-N-heptylphysostigmine; heptylphysostigmine; heptylstigmine.
C21H33N3O2; mol wt 359.51.
C 70.16%, H 9.25%, N 11.69%, O 8.90%.

Description and references

Cholinesterase inhibitor; analog of physostigmine, q.v. Prepn: M. Pomponi et al., EP 154864; M. Brufani et al., US 4831155 (1985, 1989 both to Consiglio Naz. Ricerche). Prepn of tartrate: P. G. Pagella et al., EP 298202 (1989 to Mediolanum Farm. and Consiglio Naz. Ricerche). Prepn and pharmacology: M. Marta et al., Life Sci. 43, 1921 (1988). Anticholinesterase activity: P. De Sarno et al., Neurobiochem. Res. 14, 971 (1989). Clinical cholinesterase inhibition: L. K. Unni et al., Eur. J. Clin. Pharmacol. 41, 83 (1991).

Chemical structure

Properties

Crystals from heptane, mp 60-64°; also reported as 58-62° (Marta). uv max (methanol): 303, 253 nm (ε 3300, 14200).

Derivative

Tartrate.

Nomenclature

CAS number: 121652-76-4
MF-201.
C21H33N3O2.C4H6O6; mol wt 509.59.
C 58.92%, H 7.71%, N 8.25%, O 25.12%.

Properties

Microcrystalline powder, mp 122-123°. Soly in water 70%. LD50 i.p. in mice: 35 mg/kg (De Sarno).

Therapeutic Category

Cholinergic.

Keywords

Cholinergic; Cholinesterase Inhibitor