2355

5-Methoxypsoralen, also known as bergapten, is a 5-methoxyfurocoumarin that is a derivative of psoralen with a methoxy group at the 5th position. It serves multiple roles, including as a hepatoprotective agent and a plant metabolite. Bergapten is part of the psoralens family, a group of organic heterotricyclic compounds, and is functionally related to psoralen. Bergapten is being studied in clinical trials, such as NCT00533195, which compares UVA1 phototherapy versus photochemotherapy for patients with severe generalized atopic dermatitis. It is naturally produced by numerous plant species, particularly within the carrot (Apiaceae) and citrus (Rutaceae) families. For instance, significant quantities of bergapten have been extracted from various Heracleum species in the Apiaceae family and from several Citrus species, including the bergamot orange, in the Rutaceae family. As a furanocoumarin, bergapten was first isolated from bergamot essential oil in 1834 by Kalbrunner, hence its common name. It was the first furanocoumarin to be isolated and identified. Furanocoumarins like bergapten are known for their strong photosensitizing properties when applied topically to the skin. Bergapten is associated with phytophotodermatitis, a skin inflammation that occurs when skin comes into contact with certain plant substances and is then exposed to ultraviolet light. Bergapten is particularly noted as the primary phototoxic compound causing Citrus-induced phytophotodermatitis. In addition to causing skin reactions, it can be mutagenic and induce chromosome aberrations, and with high concentrations, it can inhibit mitosis. The International Agency for Research on Cancer classifies bergapten as probably carcinogenic to humans, based on its promotion of cancer in animals. Bergapten is used in treatments for skin conditions like vitiligo and psoriasis, often in conjunction with sun exposure or artificial solar radiation. It helps the skin absorb more light and can increase the skin's tolerance to solar radiation. For vitiligo, it can help even out pigmentation, although results can vary. In psoriasis, bergapten is valued for its efficacy in oral photochemotherapy, often being preferable to 8-methoxypsoralen due to fewer side effects. Bergapten has shown potential in preventing sunlight-related skin cancer, as studies indicate that a tan developed with bergapten may result in less DNA damage. It has also demonstrated anti-tumoral effects, such as inducing autophagy in breast cancer cells, potentially through the up-regulation of the PTEN gene. Moreover, bergapten and other furanocoumarins have been implicated in inhibiting Cytochrome P450, an important enzyme in drug metabolism.

GHS Hazard Statements

• H317 (42.86%): May cause an allergic skin reaction [Warning Sensitization, Skin]

• H334 (55.71%): May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory]

• H340 (55.71%): May cause genetic defects [Danger Germ cell mutagenicity]

• H350 (61.43%): May cause cancer [Danger Carcinogenicity]

First Aid

Eyes:

• Check for contact lenses, flush eyes with water or saline for 20-30 minutes.

• Call hospital/poison control, avoid applying substances to eyes.

• Transport victim to hospital immediately, regardless of symptoms.

Skin:

• Flood affected skin with water, remove contaminated clothing, wash with soap.

• Call hospital/poison control, transport victim to hospital promptly.

Inhalation:

• Leave contaminated area, breathe fresh air, call physician.

• Provide respiratory protection, preferably SCBA.

Ingestion:

• Do not induce vomiting.

• If conscious, give water, call hospital/poison control, transport to hospital.

• If convulsing/unconscious, ensure clear airway, transport to hospital.

Other:

• Contact a physician for long-term health effects and medical monitoring recommendations based on specific factors (NTP, 1992).

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

Chemical and Physical Properties

Source: PubChem