Nicotinic acid, esters

Nicotinyl alcohol (3-pyridinylcarbinol, 3-pyridinemethanol) (27) has use as an antilipemic and peripheral vasodilator. It is available from either the reductions of nicotinic acid esters or preferably, the reduction of the nitrile to the amine followed by dia2otation and nucleophilic displacement. It is frequently adininistered in the form of the tartrate (Eig. 7). Nicotinic acid is frequently used as a salt in conjunction with basic dmgs such as the peripheral vasodilator xanthinol niacinate (28). Nicotinic acid and its derivatives have widespread use as antihyperlipidemic agents and peripheral vasodilators (1). 

An examination of some of the factors influencing the chemical and enzymatic hydrolysis of nicotinic acid esters was undertaken [45-48]. Twenty-five esters of nicotinic acid were prepared whose pro-moiety was a simple alkyl (unbranched, sec-, or /er/-alkyl), a chloroalkyl, a hydroxyalkyl, an alkoxyalkyl, a carbamoylmethyl, an aminoalkyl, a cycloalkyl, an arylalkyl, or an aryl group (Table 8.5). 

Table 1 The values (min) of nicotinic acid esters omitted from Eqs. 30 and 31, and predicted by these equations...

Pyka, A. Sliwiok, J. Use of traditional structural descriptors in QSRR analysis of nicotinic acid esters. J. Liq. Chromatogr. Relat. Technol. 2004, 27 (5), 785-798. 

An improved method to synthesize 25 involves the reduction of the methylated nicotinic acid ester 179 with sodium borohydride [126a]. 

When nicotinic acid esters are applied to the skin of patients with rheumatoid arthritis, an anomalous vasoconstriction frequently occurs instead of the usual erythema and was at first thought to offer diagnostic possibilities . It is now apparent, however, that the effect is attributable to the therapeutic use, by such patients, of acetylsalicylic acid, which is remarkably potent in retarding the development of the reaction -. ... 

Testosterone Nicotinate. I7-[(3-Pyridinylcarbon-yt)oxyJandrost-4-en-3-one testosterone 17-nicotinic acid ester Bolfortan. CjjHjtNOj mol wt 393.51. C 76.30%, H 7.94%, N 3.56%, O 12.20%, Prepared from testosterone and nicotinic acid anhydride Zirm, Weichsel, U.S. pat. 3,057,-856 (1962 to Lannacher Heilmittel). 

Juhlin L, Michaelsson G (1971) Abnormal cutaneous reactions to a nicotinic acid ester. Acta Derm Venereol (Stockh) 31 448-452... 

Fig. 2 Relationship between the experimental R values of nicotinic acid esters on sihca gel and the Rm values calculated by use of Eq. 8.

Differentiation between non-specific irritant reactions and contact urticaria may be difficult. Strong irritants, e.g., hydrochloric acid, lactic acid, and phenol, can cause clear-cut immediate whealing if the concentration is high enough, but the reactions do not usually fade away quickly. Instead, they are followed by signs of irritation (erythema, scaling, or crusting) 24 h later. Some substances have only irritant properties, e.g., benzoic acid and nicotinic acid esters, some are pure irritants, e.g., SLS, and some have both of these features, e.g., dimethyl sulfoxide (DMSO) and formaldehyde. Amin et al. (1997) provide details. 

Medicaments Alcohols, benzocaine, camphor, cantharides, capsaicin, chloroform, dimethyl sulfoxide, fi iar s balsam, iodine, methyl salicylate, methylene green, myrrh, nicotinic acid esters, resorcinol, tar extracts, tincture of benzoin, witch hazel... 

Figure 11.20 Stabilization quotient Q of nicotinic acid esters (ethyl, isopropyl, butyl, benzyl and hexyl) as a function of percentage binding of ester, (a) to three non-ionic surfactants based on PEG lOCX) O PEG l(X)0-lauryl ether, X PEG l(XX)-myristyl ether, PEG 1000 palmityl ether, and (b) to three stearyl surfactant derivatives, O PEG 900 stearyl ether, X PEG 1400 stearyl ether and PEG 2000 stearyl ether. In both (a) and (b) ionic strength is 0.083, temperature 20.0 0.1° C and borate buffer pH 10.(X) 0.02 used. Redrawn from Lippold et al [137], by permission.

XXXIII, are active in DOCA rats and in dogs. The nicotinic acid ester H-1 (XXXIV) is a hypotensive and vasodilator in spontaneous hypertensive rats. ... 

Table 5.3 Enzymatic binding strength and rate of hydrolysis for nicotinic acid esters...

---