5-methoxypsoralene

Dimethyl-5-methoxyangelicin 11 and 4,4 -dimethyl-5-methoxypsoralen 12 were added separately to 12 synthetic oligonucleotides, and their interaction and subsequent photoaddition reaction on UVA irradiation was studied <2000PCB4992>. The kinetics constant of the overall photoaddition process was determined accurately, the different intercalation sites were identified, and the value of the kinetics constant relative to each type of site was determined. 

Methoxypsoralen 188 is a naturally occurring linear furocoumarin found in citrus fruit rind and celery and parsley leaves. The use of oral or topical 5-methoxypsoralen plus UVA irradiation in the management of the skin disorders psoriasis and vitiligo was the subject of a medically oriented review <1998MI667>. 

Advances have been made in our understanding of the reactivity of the pyrimidine ring in compounds related to nucleosides and their aglycons. A 5-Me group to C-4 pyrone photoadduct obtained by reaction of thymidine and 5-methoxypsoralen in the dry state has been characterized by a wide array of spectroscopic methods [95JPP167]. The cis-syn cytosine-cytosine and... 

Citrus oils containing 5-methoxypsoralen 75 ppm4 phototox. 

Where the bergapten (5-methoxypsoralen) content of all relevant oils present in a compound has been determined, it is recommended that for applications on areas of skin exposed to sunshine, excluding bath preparations, soaps and other products which are washed off the skin, the total level of bergapten in the consumer products should not exceed 0.0015% (15ppm). This is equivalent to 0.0075% (75 ppm) in a fragrance compound used at 20% in the consumer product. 

Methoxypsoralen (=Bergapten Bergaptene Heraclin Majudin) (furanocoumarin)... 

A 55-year-old woman with psoriasis was treated with oral 5-methoxypsoralen and UVA photochemotherapy. After 40 treatments over 5 months she became unwell and complained of headaches, nausea, and abdominal pain. Laboratory tests confirmed a diagnosis of hepatitis. Six years earlier she had had flncloxacillin-indnced hepatitis. 

Photochemotherapy, which consists of oral (and sometimes topical) administration of psoralens (the furo-coumarins 5-methoxypsoralen, 8-methoxypsoralen, and trioxysalen) plus long-wave ultraviolet radiation, known as PUVA, is a well-established effective treatment for psoriasis, which has also been used for vitiligo (1), mycosis fungoides, alopecia areata, dyshidrotic eczema, atopic dermatitis, and certain other skin diseases. Guidelines for treatment have been recommended (2,3). 

Hypersensitivity reactions occur infrequently and have included drug fever, skin rashes, and bronchial asthma. Anaphylaxis to 5-methoxypsoralen has been reported... 

A 36-year-old woman had been treated for a polymorphic light eruption with two annual courses of PUVA, three times weekly for 6 weeks, plus oral 5-methoxypsoralen 60 mg, without any adverse effects. However, during the fourth course, 30 minutes after... 

Synonyms Psoralen and UVA Photochemotherapy Light therapy 8-Methoxypsoralen (8-MOP) 5-Methoxypsoralen (5-MOP) 4,5, 8-Trimethyl-psoralen (TMP)... 

PUVA is the acronym originally introduced to describe the combined administration of psoralen and subsequent exposure to high-intensity ultraviolet radiation from an artificial source (UVA). In the United States, orally administered 8-methoxypsor-alen (8-MOP) is the psoralen most frequently used in combination with UVA light therapy and will be the focus of this discussion. However, the term PUVA also refers to therapy with other oral and topical psoralens, most commonly 4,5, 8-trimethylpsoralen (TMP), a synthetic psoralen, and 5-methoxypsoralen (5-MOP), not available in the United States. 

Clark SM, Wilkinson SM. Phototoxic contact dermatitis from 5-methoxypsoralen in aromatherapy oil. Contact Dermatitis 1998 38 289-290. 

Ashwood-Smith MJ, Poulton GA, Barker M, Mildenberger M. 5-Methoxypsoralen, an ingredient in several suntan preparations, has lethal mutagenic and clastogenic properties. Nature 1980 285 407 109. 

Bergapten (5-methoxypsoralen) [484-20-8] M 216.2, m 190-193 , 191-193. Crystallise it from EtOH or aqueous MeOH, and it sublimes in vacuo. Its properties are similar to those of its 9-methoxy isomer (xanthotoxin, see below). It is slightly soluble in C6H6, CHCI3 and AcOH but insoluble in H2O. Its fluorescence has A,ex at 352nm with X,em at 480nm. It is a DNA intercalator and possible carcinogen. [Howell Robertson J Chem Soc 293 1937, Boyer et al. Biochemistry 27 3011 1988, Beilstein 19/6 V 4.]... 

Craw, M., Bensasson, R.V., Ronfard-Haret, J.C., Sa e Melo, M.T., and Truscott, T.G. (1983) Some phtophysical properties of 3-carbethoxypsoralen, 8-methoxypsoralen and 5-methoxypsoralen triplet states, Photochem. Photobiol., 37, 611-615. 

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