84. Acetylcarnitine

Nomenclature

CAS number: 3040-38-8; 14992-62-2 (dl-form)
(2R)-2-(Acetyloxy)-3-carboxy-N,N,N-trimethyl-1-propanaminium inner salt; l-(3-carboxy-2-hydroxypropyl)trimethylammonium hydroxide inner salt acetate; acetyl-l-carnitine; ALCAR.
C9H17NO4; mol wt 203.24.
C 53.19%, H 8.43%, N 6.89%, O 31.49%.

Description and references

Naturally occurring ester of carnitine, q.v.; important acetyl donor in metabolic processes. Prepn from carnitine extracted from meat: R. Engeland, Ber. 42, 2457 (1909); R. Krimberg, W. Wittandt, Biochem. Z. 251, 229 (1932); E. Strack et al., Z. Physiol. Chem. 238, 183 (1936). Resolution of isomers: K. Brendel, R. Bressler, Biochim. Biophys. Acta 137, 98 (1967). Extraction from calf brain tissue: E. A. Hosein, A. Orzeck, Int. J. Neuropharmacol. 3, 71 (1964). Enzymatic determn in serum: K. Tomita et al., J. Pharm. Biomed. Anal. 24, 1147 (2001). Clinical trial in cognitive impairment in the elderly: G. Salvioli, M. Neri, Drugs Exp. Clin. Res. 20, 169 (1994). Review of pharmacology in the CNS: L. Janiri, E. Tempesta, Int. J. Clin. Pharmacol. Res. 3, 295-306 (1983); of bioactivity and clinical studies in Alzheimer's disease and geriatric depression: J. W. Pettegrew et al., Mol. Psychiatry 5, 616-632 (2000); of pharmacokinetics and metabolism: C. J. Rebouche, Ann. N.Y. Acad. Sci. 1033, 30-41 (2004).

Chemical structure

Properties

Hygroscopic crystals, mp 145° (dec). [α]D20 19.52° (c = 6). Very sol in water, alcohol. Practically insol in ether.

Derivative

Hydrochloride.

Nomenclature

CAS number: 5080-50-2
Acetyl-l-carnitine chloride; levacecarnine hydrochloride; ST-200; Branigen (GSK); Nicetile (Sigma-Tau); Normobren (Medosan); Zibren (Sigma-Tau).
C9H17NO4.HCl; mol wt 239.70.
C 45.10%, H 7.57%, N 5.84%, O 26.70%, Cl 14.79%.

Properties

Stable crystals, mp 187° (dec). Also reported as small rod-shaped crystals from butanol, mp 181° (Strack). [α]D20 26.9° (c = 9). [α]D25 28° (c = 2 in water). Very sol in water, sol in alcohol. Practically insol in ether.

Therapeutic Category

Nootropic.

Keywords

Nootropic