Compound: methoxsalen
SMILES: O=c1oc2c(OC)c3occc3cc2cc1
InChIKey: QXKHYNVANLEOEG-UHFFFAOYSA-N
Synonyms: methoxsalen, 8-Methoxypsoralen, 298-81-7, XANTHOTOXIN, Meladinine, Oxsoralen, 8-MOP, 9-Methoxy-7H-furo[3,2-g]chromen-7-one, Oxypsoralen, Meloxine, Puvalen, Xanthotoxine, Ammoidin, Meladinin, Uvadex, Meladoxen, Ammodin, 8-Methoxypsoralene, New-Meladinin, Geroxalen, Zanthotoxin, Puvamet, Psoralon-MOP, 9-Methoxypsoralen, Oxsoralen Ultra, 8-Methoxyfuranocoumarin, 9-Methoxy-7H-furo[3,2-g][1]benzopyran-7-one, O-methylxanthotoxol, Vitpso, Ultra Mop, 8-Methoxy-2',3',6,7-furocoumarin, 7H-Furo[3,2-g][1]benzopyran-7-one, 9-methoxy-, Metoxalen, Metoxaleno, NCI-C55903, 8-methoxsalen, 8-Methoxy-4',5',6,7-furocoumarin, NSC45923, 6-Hydroxy-7-methoxy-5-benzofuranacrylic acid delta-lactone, 8-Methoxy-4',5':6,7-furocoumarin, DTXSID8020830, 7H-Furo(3,2-G)(1)benzopyran-7-one, 9-methoxy-, 8-Methoxy-(furano-3'.2':6.7-coumarin), 8-Methoxy-[furano-3'.2':6.7-coumarin], U4VJ29L7BQ, NSC-45923, 9-Methoxy-7H-furo(3,2-g)(1)benzopyran-7-one, CHEBI:18358, 5-Benzofuranacrylic acid, 6-hydroxy-7-methoxy-, delta-lactone, DTXCID40830, SM-88 COMPONENT METHOXSALEN, Methoxa Dome, 8 Methoxypsoralen, methoxypsoralen, 8MOP, 9-methoxy-7H-furo(3,2-g)chromen-7-one, 8 MOP, Mopsoralen, Puvasoralen, Puvasoralen-8, RefChem:41982, 8-Methoxy(furano-3',2':6,7-coumarin), Methoxa-Dome, Oxsoralen-ultra, Methoxalen, Oxsoralen lotion, 8-MP, 9-methoxyfuro[3,2-g]chromen-7-one, Methoxy-8-psoralen, 8-methoxy psoralen, MFCD00005009, NSC 45923, Methoxsalen (Oxsoralen), 9-Methoxyfuro(3,2-g)chromen-7-one, CHEMBL416, 9-(methyloxy)-7H-furo[3,2-g]chromen-7-one, Proralone-mop, 9-methoxyfurano[3,2-g]chromen-2-one, Meladinin (VAN), NCGC00016418-07, CAS-298-81-7, Methoxaten, Oxoralen, ST041029, Deltapsoralen, Dltasoralen, Methoxsalene, Xanthatoxin, Methoxsalen, 8-, SMR000071170, CCRIS 2083, HSDB 2505, 8-Methoxypsoralen with ultraviolet A therapy, OXSORALEN (TN), SR-01000629727, EINECS 206-066-9, Methoxsalen plus ultraviolet radiation, UNII-U4VJ29L7BQ, BRN 0196453, Methoxsalen [USP:BAN:JAN], 9-Methoxy-7H-furo(3,2-g)benzopyran-7-one, 8-methoxylpsoralen, Prestwick_661, Xanthotoxin,Methoxsalen, Methoxsalen (Standard), Spectrum_001023, 8-Methoxy(furano-3'.2':6.7-coumarin), METHOXSALEN [MI], Prestwick0_000479, Prestwick1_000479, Prestwick2_000479, Prestwick3_000479, Spectrum2_001052, Spectrum3_000499, Spectrum4_000052, Spectrum5_001891, METHOXSALEN [JAN], UVADEX (TN), Xanthotoxin (Methoxsalen), X0009, METHOXSALEN [HSDB], METHOXSALEN [IARC], Epitope ID:613448, Methoxsalen (JP18/USP), METHOXSALEN [VANDF], 8-MOP;Xanthotoxin;Ammoidin, 7H-Furo[3, 9-methoxy-, METHOXSALEN [MART.], Oprea1_166319, SCHEMBL19168, BSPBio_000618, BSPBio_001997, KBioGR_000543, KBioSS_001503, METHOXSALEN [USP-RS], METHOXSALEN [WHO-DD], 5-19-06-00015 (Beilstein Handbook Reference), 8MO, MLS000062633, MLS002303011, DivK1c_000763, SPECTRUM1500400, SPBio_001004, SPBio_002557, 8-Methoxy-6,7-furanocoumarin, BPBio1_000680, MEGxp0_000095, orb2281208, orb3025346, Xanthotoxin, analytical standard, 8-Methoxypsoralen (Xanthotoxin), Methoxsalen (8-Methoxypsoralen), SCHEMBL29376525, ACon1_000174, GTPL12457, HMS502G05, KBio1_000763, KBio2_001503, KBio2_004071, KBio2_006639, KBio3_001497, METHOXSALEN [ORANGE BOOK], 8-Methoxy-2',6,7-furocoumarin, 8-Methoxy-4',6,7-furocoumarin, NINDS_000763, HMS1569O20, HMS1920N05, HMS2091D20, HMS2096O20, HMS2269P03, HMS3259L13, HMS3655B05, HMS3884K16, HMS5080L07, Pharmakon1600-01500400, METHOXSALEN [USP MONOGRAPH], 5-Benzofuranacrylic acid, 6-hydroxy-7-methoxy-, .delta.-lactone, Tox21_110432, Tox21_201767, Tox21_302816, 8-Methoxypsoralen;Xanthotoxin;8-MOP, BDBM50041234, CCG-36366, EBC-11074, HY-30151R, NSC757114, s1952, SBB005950, STK735539, WLN: T C566 DO LVOJ BO1, 8-Methoxypsoralen, analytical standard, AKOS000277012, Tox21_110432_1, 9-Methoxy-furo[3,2-g]chromen-7-one, AC-4259, CS-1983, DB00553, DS-5159, FM08242, METHOXSALEN COMPONENT OF SM-88, NC00652, NSC-757114, SDCCGMLS-0042377.P002, IDI1_000763, 8-methoxy-2'',3'',6,7-furocoumarin, 8-methoxy-4'',5'':6,7-furocoumarin, NCGC00016418-01, NCGC00016418-02, NCGC00016418-03, NCGC00016418-04, NCGC00016418-05, NCGC00016418-06, NCGC00016418-08, NCGC00016418-09, NCGC00016418-10, NCGC00016418-11, NCGC00016418-12, NCGC00016418-14, NCGC00016418-15, NCGC00060938-02, NCGC00060938-03, NCGC00060938-04, NCGC00060938-05, NCGC00060938-06, NCGC00178871-01, NCGC00178871-02, NCGC00178871-03, NCGC00256435-01, NCGC00259316-01, HY-30151, NCI60_004085, SBI-0051443.P003, NS00004875, SW167762-4, 8-methoxy-[furano-3''.2'':6.7-coumarin], 9-Methoxy-7H-furo[3,2-g]chromen-7-one #, EN300-52504, C01864, D00139, AB00052042-14, AB00052042-15, AB00052042_16, AB00052042_17, 9-METHOXY-2H-FURO[3,2-G]CHROMEN-2-ONE, AH-357/03514063, F239129, Q408570, SR-01000629727-2, SR-01000629727-4, BRD-K63430059-001-03-2, BRD-K63430059-001-06-5, BRD-K63430059-001-09-9, BRD-K63430059-001-16-4, BRD-K63430059-001-17-2, Z754918916, Methoxsalen, United States Pharmacopeia (USP) Reference Standard, 12692-94-3
Theoretical properties:
molecular_formula: C12H8O4
molecular_weight: 216.19 g/mol
exact_mass: 216.04225873 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 1
heavy_atom_count: 16
topological_polar_surface_area: 48.7 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Silky needles from hot water or benzene + petroleum ether
color: Silky needles from hot water or benzene + petroleum ether
odor: Odorless
melting_point: 298 °F (NTP, 1992)
solubility: less than 1 mg/mL at 59 °F (NTP, 1992)
Descriptions:
pubchem: 8-Methoxypsoralen with ultraviolet A therapy can cause cancer according to California Labor Code.
chebi: A member of the class of psoralens that is 7<em>H</em>-furo[3,2-<em>g</em>]chromen-7-one in which the 9 position is substituted by a methoxy group. It is a constituent of the fruits of <em>Ammi majus</em>. 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.
chembl: METHOXSALEN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Methoxsalen (or Xanthotoxin, 8-methoxypsoralen) sold under the brand name Oxsoralen and Melanocyl among others, is a medication used to treat psoriasis, eczema, vitiligo, and some cutaneous lymphomas in conjunction with exposing the skin to ultraviolet (UVA) light from lamps or sunlight. Methoxsalen modifies the way skin cells receive the UVA radiation, allegedly clearing up the disease. Levels of individual patient PUVA exposure were originally determined using the Fitzpatrick scale. The scale was developed after patients demonstrated symptoms of phototoxicity after oral ingestion of methoxsalen followed by PUVA therapy.
Chemically, methoxsalen is a derivative of psoralen and belongs to a class of organic natural molecules known as furanocoumarins. They consist of coumarin annulated with furan. It can also be injected and used topically.