Title: Methoxsalen
CAS Registry Number: 298-81-7
CAS Name: 9-Methoxy-7H-furo[3,2-g][1]benzopyran-7-one
Additional Names: 6-hydroxy-7-methoxy-5-benzofuranacrylic acid d-lactone; 9-methoxypsoralen; 8-methoxy-4¢,5¢:6,7-furocoumarin; 8-methoxy[furano-3¢,2¢:6,7-coumarin]; ammoidin; xanthotoxin; 8-methoxypsoralen; 8-MOP; 8-MP
Trademarks: Meladinine (DB Pharma); 8-MOP (Valeant); Oxsoralen (Valeant)
Molecular Formula: C12H8O4
Molecular Weight: 216.19
Percent Composition: C 66.67%, H 3.73%, O 29.60%
Literature References: Naturally occurring analog of psoralen, q.v., found in spp. of Leguminosae, Umbelliferae, and Rutaceae. Isolation: Priess, Ber. Dtsch. Pharm. Ges. 21, 227 (1911); Thoms, Ber. 44, 3325 (1911); 45, 3705 (1912); Jois et al., J. Indian Chem. Soc. 10, 41 (1933); Späth et al., Ber. 73, 1361 (1933); Schonberg, Sina, Nature 160, 468 (1947); 161, 481 (1948); J. Am. Chem. Soc. 72, 4826 (1950). Synthesis: Späth, Pailer, Ber. 69, 767 (1936); Lagercrantz, Acta Chem. Scand. 10, 647 (1956); Stanley, Vannier, US 2889337 (1959 to USDA); P. Nore, E. Honkanen, J. Heterocycl. Chem. 17, 985 (1980). Use in treatment of psoriasis and mycosis fungoides: J. A. Parrish et al., Int. J. Dermatol. 19, 379 (1980). Acute toxicity data: Hakim et al., J. Pharmacol. Exp. Ther. 131, 394 (1961). Phototoxicity study: A. Kornhauser et al., Science 217, 733 (1982). Comprehensive description: M. A. Loutfy, M. A. Hassan, Anal. Profiles Drug Subs. 9, 427-454 (1980). Review of use in photochemotherapy: T. F. Anderson, J. J. Voorhees, Annu. Rev. Pharmacol. Toxicol. 20, 235-258 (1980); Acta Derm. Venereol. Suppl. 106, 9-42 (1982).
Properties: Silky needles from hot water or benzene + petr ether, long rhombic prisms from alcohol + ether. mp 148°. Odorless. Bitter taste followed by tingling sensation. pH 5.5. uv max: 219, 249, 300 nm (log e 4.32, 4.35, 4.06). Practically insol in cold water. Sparingly sol in boiling water, liq petrolatum, ether. Sol in boiling alcohol, acetone, acetic acid, vegetable fixed oils, propylene glycol, benzene. Freely sol in chloroform. Sol in aq alkalies with ring cleavage, but is reconstituted upon neutralization. LD50 i.p. in rats: 470 ±30 mg/kg (Hakim).
Melting point: mp 148°
Absorption maximum: uv max: 219, 249, 300 nm (log e 4.32, 4.35, 4.06)
Toxicity data: LD50 i.p. in rats: 470 ±30 mg/kg (Hakim)
CAUTION: Methoxsalen with ultraviolet A (long wave light) therapy (PUVA) is listed as a known human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-165.
Therap-Cat: Pigmentation agent.
Keywords: Pigmentation Agent. |