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8-Methoxypsoralen

Basic information Description References Safety Related Supplier

8-Methoxypsoralen Basic information

Product Name:
8-Methoxypsoralen
CAS:
298-81-7
MF:
C12H8O4
MW:
216.19
EINECS:
206-066-9
Mol File:
298-81-7.mol
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8-Methoxypsoralen Chemical Properties

Melting point:
148-150 °C(lit.)
Boiling point:
276.6°C (rough estimate)
Density 
1.1344 (rough estimate)
refractive index 
1.4270 (estimate)
storage temp. 
-20°C Freezer, Under Inert Atmosphere
solubility 
H2O: slightly soluble
form 
Needle-Like Crystals or Powder
color 
white to yellow
Water Solubility 
PRACTICALLY INSOLUBLE
Merck 
14,5988
BRN 
196453
CAS DataBase Reference
298-81-7(CAS DataBase Reference)
NIST Chemistry Reference
Methoxsalen(298-81-7)
IARC
1 (Vol. 24, Sup 7, 100A) 2012
EPA Substance Registry System
Methoxsalen (298-81-7)
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Safety Information

Hazard Codes 
Xn,T
Risk Statements 
22-43-46-45-34
Safety Statements 
36/37-53-45-36/37/39-26
RIDADR 
3216
WGK Germany 
3
RTECS 
LV1400000
10
TSCA 
Yes
HS Code 
29322090
Hazardous Substances Data
298-81-7(Hazardous Substances Data)
Toxicity
LD50 i.p. in rats: 470 ±30 mg/kg (Hakim)

MSDS

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8-Methoxypsoralen Usage And Synthesis

Description

8-methoxypsoralen (also known as methoxsalen) is a naturally occurring furocoumarin compound existing in several species of plants such as Psoralea corylifolia. It is a photoactive substance that can form DNA adducts upon UVA irradiation. It is a drug used for the treatment of psoriasis, eczema, vitiligo, and some kinds of cutaneous lymphomas associated with the exposure of skin to the UVA or light from lamps or sunlight. Its mechanism of action is through inhibiting the synthesis of the deoxyribonucleic acid (DNA). After the activation, it can preferentially bind to the guanine and cytosine molecules of DNA, further leading to the cross-linking of DNA, thus inhibiting the DNA synthesis. It can further inhibit the RNA and protein synthesis at high concentration. It is extracted from Ammi majus.

References

https://www.drugbank.ca/drugs/DB00553
https://en.wikipedia.org/wiki/Methoxsalen

Chemical Properties

White to cream-colored, crystalline solid; odorless. Slightly soluble in alcohol; practically insoluble in water. Combustible.

Originator

Oxsoracen,Eider,US,1955

Uses

antipsoriatic, pigmentation agent

Uses

Naturally occurring analog of Psoralen (P839800). Use in treatment of psoriasis and mycosis fungoides.

Uses

For the treatment of psoriasis and vitiligo

Uses

A potent suicide inhibitor of cytochrome P-450.

Uses

Naturally occurring analog of psoralen. Use in treatment of psoriasis and mycosis fungoides

Indications

Methoxsalen has effects similar to those of trioxsalen. Methoxsalen is superior to trioxsalen in producing erythema and tanning and is the drug used in PUVA therapy. Methoxsalen is also available as a 1% lotion.

Definition

ChEBI: A member of the class of psoralens that is 7H-furo[3,2-g]chromen-7-one in which the 9 position is substituted by a methoxy group. It is a constituent of the fruits of Ammi majus. Like other psoralens, trioxsalen causes photosensitization of the skin. It is administered topically or orally in conjunction with UV-A for phototherapy treatment of vitiligo and severe psoriasis.

Manufacturing Process

It has been found that the compound 8-geranoxy psoralen is present in citrus oils, particularly lemon and lime oils. This compound can be isolated from the oil by a process which involves primarily absorption on an adsorbent material followed by elution with a suitable solvent.
(A) Cleavage of 8-Geranoxypsoralen: 275 mg of 8-geranoxypsoralen was dissolved with mechanical stirring in 4 ml glacial acetic acid. After 10 minutes,one drop of concentrated sulfuric acid was added to the solution. In 4 minutes thereafter a light tan precipitate began to form. Stirring was continued for 35 minutes and the reaction mixture was refrigerated for one hour and 20 minutes. The precipitate was then removed by suction filtration and washed on the filter with glacial acetic acid followed by ice-cold ethyl ether. The product, 8-hydroxypsoralen, weighed 115 mg, that is, 74% of theory.
(B) Methylation of 8-Hydroxypsoralen: 115 mg of 8-hydroxypsoralen was dissolved in 10 ml absolute methanol, an excess of diazomethane dissolved in ether was added and the mixture allowed to stand at room temperature with occasional stirring for 3 hours. The next day the reaction mixture was reduced in volume to 3 ml by evaporation on the steam bath and the concentrate was held in a refrigerator overnight. The next day, fine needles (80 mg) of 8- methoxypsoralen were filtered from the solution. The compound had a MP of 145 to 146°C and was obtained in a yield of 65% of theory.
There is also a wholly synthetic route to Methoxsalen as outlined by Kleeman and Engel.

brand name

8-Mop (Valeant); Oxsoralen (Valeant); Uvadex (Therakos).

Therapeutic Function

Dermal pigmentation enhancer

General Description

Odorless white to cream-colored crystalline solid. Bitter taste followed by tingling sensation.

Air & Water Reactions

Sensitive to light and air. Insoluble in water.

Reactivity Profile

8-Methoxypsoralen is incompatible with strong oxidizing agents.

Fire Hazard

Flash point data for 8-Methoxypsoralen are not available; however, 8-Methoxypsoralen is probably combustible.

Contact allergens

This fur(an)ocoumarin is an phototoxic compound that causes phototoxic dermatitis. Many plants of the Apiaceae–Umbelliferae and most of the Rutaceae family contain 5-methoxypsoralen and 8-methoxypsoralen. Their spectra is in the UVA range (300–360 nm). It is used in combination with UVA to treat various skin disorders such as psoriasis.

Safety Profile

Confirmed carcinogen. Poison by intraperitoneal route. Moderately toxic by ingestion and subcutaneous routes. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes. A drug used to treat slun diseases.

Purification Methods

Purify xanthotoxin by recrystallisation from *C6H6/pet ether (b 60-80o) to give silky needles, or from EtOH/Et2O to give rhombic prisms or from hot H2O to give needles. It is soluble in aqueous alkali due to ring opening of the cyclic lactone but recyclises upon acidification. It has UV max in EtOH at 219, 249 and 300nm (log  4.32, 4.35 and 4.06) and 1H NMR in CDCl3 with at 7.76 (d, 1H, J 10 Hz), 7.71 (d, 1H, J 2.5 Hz), 7.38 (s, 1H), 6.84 (d, 1H, J 2.5 Hz), 6.39 (d, 1H, J 10 Hz) and 4.28 (s, 3H)ppm. [Nore & Honkanen J Heterocycl Chem 17 985 1980.] It is a DNA intercalator, is used in the treatment of dermal diseases, and is a human carcinogen [Tessman et al. Biochemistry 24 1669 1985.] [Beilstein 19 I 711, 19/6 V 15.]

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8-MethoxypsoralenSupplierMore

Changzhou Pumelo Co.,Ltd. Gold
Tel:
0519-81698808
Email:
pml@pmlchem.com
Wuxi Helen Biotechnology Co., Ltd., Gold
Tel:
18013409632 0510-85629785-
Email:
sales@reading-chemicals.com
J & K SCIENTIFIC LTD.
Tel:
400-666-7788 010-82848833-
Email:
jkinfo@jkchemical.com;market6@jkchemical.com
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel:
400-660-8290 21-61259100-
Email:
sh@meryer.com
INTATRADE GmbH
Tel:
+49 3493/605464
Email:
sales@intatrade.de
Basic information Description References Safety Related Supplier