2843. Deanol

Nomenclature

CAS number: 108-01-0
2-(Dimethylamino)ethanol; N,N-dimethylethanolamine; β-dimethylaminoethyl alcohol; N,N-dimethyl-2-hydroxyethylamine; DMAE.
C4H11NO; mol wt 89.14.
C 53.90%, H 12.44%, N 15.71%, O 17.95%.

Description and references

Naturally occurring precursor of choline, q.v.; found in high concentrations in salmon, sardines, and anchovies. Prepn from equimolar amounts of ethylene oxide and dimethylamine: Knorr, Ber. 37, 3508 (1904); Hanhart, Ingold, J. Chem. Soc. 1927, 1012. Determn in animal tissues: C. G. Honegger, R. Honegger, Nature 184, 550 (1959). GCMS determn with choline: D. J. Jenden et al., Life Sci. 23, 291 (1978). Pharmacology and stimulant effect: C. C. Pfeiffer et al., Science 126, 610 (1959). Clinical trial in hyperkinetic children: N. Coleman et al., Psychosomatics 17, 68 (1976); in involuntary movement disorders: D. E. Casey, Dis. Nerv. Syst. 38, 7 (1977). Use in organic synthesis: Z. Lu, R. J. Twieg, Tetrahedron 61, 903 (2005); as corrosion inhibitor: G. Batis et al., American Concrete Inst. Spec. Publ. SP-217, 469 (2003). Review of role in cosmetic dermatology: R. Grossman, Am. J. Clin. Dermatol. 6, 39-47 (2005).

Chemical structure

Properties

Very faintly yellow liquid with fishy odor. Flammable and corrosive. d420 0.8866. bp758 135°. nD20 1.43. Vapor pressure (20°): 6.12 mm Hg. Vapor density: 3.1 g/l. Flash point (closed cup): 39°C (102°F). Autoignition temp: 245°C. Miscible with water, alcohol, ether. Keep tightly closed, away from heat and open flame.

Derivative

Aceglumate.

Nomenclature

CAS number: 3342-61-8
Cleregil (Merck KGaA); Risatarun (Ravensberg).
C4H11NO.C7H11NO5; mol wt 278.30.
C 47.47%, H 7.97%, N 10.07%, O 34.49%.

Description and references

Prepn: FR M2487 (1964 to Interco Fribourg), C.A. 61, 12085c (1964).

Properties

Sol in water.

Derivative

Acetamidobenzoate.

Nomenclature

CAS number: 3635-74-3
Deaner.
C4H11NO.C9H9NO3; mol wt 268.31.
C 58.19%, H 7.51%, N 10.44%, O 23.85%.

Description and references

Prepn: GB 879259 (1957 to Riker Labs); A. Lasslo et al., J. Am. Pharm. Assoc. Sci. Ed. 48, 345 (1959).

Properties

Crystals from absolute ethanol + ethyl acetate, mp 159-161.5°. Sol in water.

Derivative

Bitartrate.

Nomenclature

CAS number: 5988-51-2
C4H11NO.C4H6O6; mol wt 239.22.
C 40.17%, H 7.16%, N 5.86%, O 46.82%.

Properties

White powder, mp 109-113°. [α]D20 +18° (c = 3% in water). Sol in water. LD50 in mice, rats (g/kg): 3.1, 2.6 orally (Pfeiffer).

Derivative

Hemisuccinate.

Nomenclature

Tonibral (Bouchara); Rischiaril (Piam).
C4H11NO.C4H6O4; mol wt 207.22.
C 46.37%, H 8.27%, N 6.76%, O 38.60%.

Properties

White, hygroscopic crystalline powder. Very soluble in water, ethanol; sparingly sol in chloroform, benzene.

Use

Solvent and ligand in organic synthesis; accelerator in epoxy resin formulations. As corrosion inhibitor in steel-reinforced concrete. Salts as dietary supplement, tonic. In cosmetics as antiwrinkle and skin firming agent.