1799. Carbinoxamine

Nomenclature

CAS number: 486-16-8
2-[(4-Chlorophenyl)-2-pyridinylmethoxy]-N,N-dimethylethanamine; 2-[p-chloro-α-(2-dimethylaminoethoxy)benzyl]pyridine; paracarbinoxamine.
C16H19ClN2O; mol wt 290.79.
C 66.09%, H 6.59%, Cl 12.19%, N 9.63%, O 5.50%.

Description and references

Prepn: Tilford, Shelton, US 2606195 (1952 to Wm. S. Merrell); Swain, US 2800485 (1957 to McNeil Labs.). Prepn of l-form: GB 905993 (1962 to McNeil Labs.), C.A. 58, 5644a (1962). Abs config of l-form: V. Barouh et al., J. Med. Chem. 14, 834 (1971). Pharmacology and toxicology: R. Cahen, Ann. Pharm. Fr. 20, 463 (1962). GLC determn in serum: D. J. Hoffman et al., J. Pharm. Sci. 72, 1342 (1983).

Chemical structure

Properties

Liquid, bp0.1 158-162°.

Derivative

Hydrochloride.
C16H19ClN2O.HCl; mol wt 327.25.
C 58.72%, H 6.16%, Cl 21.67%, N 8.56%, O 4.89%.

Properties

Crystals from isopropanol + ethyl acetate, dec 162-164°. Sol in water.

Derivative

Maleate.

Nomenclature

CAS number: 3505-38-2
Allergefon (Lafon); Clistin (McNeil); Ciberon (Taisho); Lergefin (Larma); Polistin T-Caps (Trommsdorff).
C16H19ClN2O.C4H4O4; mol wt 406.86.
C 59.04%, H 5.70%, Cl 8.71%, N 6.89%, O 19.66%.

Properties

Bitter crystals from ethyl acetate, mp 117-119°. Freely sol in water, alcohol, chloroform. Very slightly sol in ether. pH of 1% aq soln 4.6-5.1. LD50 in mice (mg/kg): 166 i.p. (Cahen).

Derivative

l-Form.

Nomenclature

Levocarbinoxamine; rotoxamine; McN-R-73-Z.

Properties

bp0.5 143-144°. nD20 1.5522. [α]D25 -6.8° (c = 2 in methanol).

Derivative

l-Form d-tartrate.

Nomenclature

CAS number: 49746-00-1
Twiston (McNeil).
C16H19ClN2O.C4H6O6; mol wt 440.87.
C 54.49%, H 5.72%, Cl 8.04%, N 6.35%, O 25.40%.

Properties

Crystals from isopropanol, mp 143-144.5°. [α]D25 +37.2° (c = 20 in methanol).

Therapeutic Category

Antihistaminic.

Keywords

Antihistaminic; Aminoalkylethers