3967. Fencamine

Nomenclature

CAS number: 28947-50-4
3,7-Dihydro-1,3,7-trimethyl-8-[[2-[methyl(1-methyl-2-phenylethyl)amino]ethyl]amino]-1H-purine-2,6-dione; 8-[[2-[methyl(α-methylphenethyl)amino]ethyl]amino]caffeine; 8-[2-(N,α-dimethyl-β-phenyl)ethylamino]-1,3,7-trimethyl-2,6-dioxopurine; N1-(1,3,7-trimethyl-2,6-dioxopurin-8-yl)-N2-(1-methyl)phenethyl-N2-methylethylenediamine; N-8-caffeyl-N′-methyl-N′-(α-methylphenethyl)ethylenediamine; phencamine; ST-374.
C20H28N6O2; mol wt 384.48.
C 62.48%, H 7.34%, N 21.86%, O 8.32%.

Description and references

Prepn: ES 347509; ES 352077 (both 1969 to Labs. Miquel); Pitarch et al., Quim. Ind. (Madrid) 17, 71 (1971). Pharmacology: eidem, ibid. 76. Colorimetric and TLC determn in urine: J. Mallol et al., Arzneim.-Forsch. 24, 1301 (1974). Toxicity data: E. Usdin, D. H. Efron, Psychotropic Drugs and Related Compounds (National Institute of Mental Health, Rockville, MD, 2nd ed., 1972) p 229. Clinical trial in depression: P. G. Quiros e Isla, Rev. Clin. Esp. 119, 437 (1970).

Chemical structure

Properties

Crystals from methanol, mp 150-152°.

Derivative

Hydrochloride.

Nomenclature

CAS number: 63918-50-3
Altimina (Miquel); Sicoclor (Gramon).
C20H28N6O2.HCl; mol wt 420.94.
C 57.07%, H 6.94%, N 19.96%, O 7.60%, Cl 8.42%.

Properties

Slightly hygroscopic, bitter crystals, decomp 278-279°. uv max (water): 296 nm (E1%1cm 398). Sol in water; slightly sol in many organic solvents. LD50 in rats, mice (mg/kg): 93, 82 i.p.; 508, 418 orally (Usdin, Efron).

Therapeutic Category

Analeptic.

Keywords

Antidepressant; Bicyclics