Basic information
- CAS
3902-71-4- Standard SMILES
Cc1cc2cc3c(C)cc(=O)oc3c(C)c2o1- InChIKey
FMHHVULEAZTJMA-UHFFFAOYSA-N- Molecular formula
- C14H12O3
- Average molar mass
- 228.24 g/mol
- Monoisotopic mass
- 228.07864424
Overview
Trioxsalen is 7H-Furo[3,2-g]chromen-7-one in which positions 2, 5, and 9 are substituted by methyl groups. Like other psoralens, trioxsalen causes photosensitization of the skin. It is administered orally in conjunction with UV-A for phototherapy treatment of vitiligo. After photoactivation it creates interstrand cross-links in DNA, inhibiting DNA synthesis and cell division, and can lead to cell injury; recovery from the cell injury may be followed by increased melanisation of the epidermis. It has a role as a photosensitizing agent and a dermatologic drug.
Names & identifiers
- Preferred name
- Trimethylpsoralen
- IUPAC
- 2,5,9-trimethylfuro[3,2-g]chromen-7-one
- English name
- TRIOXSALEN
- Molecular formula
- C14H12O3
- Molecular weight
- 228.24
Names & synonyms
trioxsalen3902-71-4TrioxysalenTrimethylpsoralen4,5',8-TrimethylpsoralenTrioxisalenoTrioxysalene2',4,8-TrimethylpsoralenTrioxysalenumNSC710472,5,9-trimethylfuro[3,2-g]chromen-7-oneTmp (psoralen)
Show more names
LACTONENSC-71047TrioxalenTrioxsaleTrixsalenrioxsalenTRISORALENElder 8011
DTXSID3023716NSC 710477H-Furo[3,2-g][1]benzopyran-7-one, 2,5,9-trimethyl-Y6UY8OV51T2,5,9-Trimethyl-7H-furo(3,2-g)(1)benzopyran-7-one7H-Furo(3,2-g)(1)benzopyran-7-one, 2,5,9-trimethyl-2,5,9-Trimethyl-7H-furo[3,2-g][1]benzopyran-7-oneDTXCID403716
Database identifiers
- CAS
3902-71-4- PubChem CID
- 5585
- DTXSID
DTXSID3023716- ChEMBL
CHEMBL1475- ChEBI
CHEBI:28329- UNII
- Y6UY8OV51T
Properties
Computed structural properties
- XLogP
- 3
- Topological polar surface area
- 39.4 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 0
- Heavy atoms
- 17
- Formal charge
- 0
- Complexity
- 374
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesFusion temperature
LogP3.25
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physical DescriptionSolid
Collision Cross Section
147.4 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
146.69 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 229 · 229-231 °C(lit.)
- Boiling point
- 310.05 °C · 310.05°C (rough estimate)
- Density
- 1.2196 · 1.2196 (rough estimate)
- refractive index
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
P203, P260, P264, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P318, P321, P363, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Other Safety InformationIMAP assessments - 7H-Furo[3,2-g][1]benzopyran-7-one, 2,5,9-trimethyl-: Human health tier I assessment
Hazard Classes and CategoriesSkin Corr. 1B (100%)
Toxicology
Carcinogen Classification
4,5',8-Trimethylpsoralen
Group 3: Not classifiable as to its carcinogenicity to humans
Volume 40: (1986) Some Naturally Occurring and Synthetic Food Components, Furocoumarins and Ultraviolet Radiation
1987
1987
Safety data
- F
- 8-10
- PPE
- Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- LV1576000
- ridadr
- UN 1759 8/PG 1
- hs_code
Chemistry & industry
Pharmacology
ATC Code
D - Dermatologicals
D - Dermatologicals
QD - Dermatologicals
QD - Dermatologicals
PharmacodynamicsTrioxsalen ispharmacologically inactive but when exposed to ultraviolet radiation or sunlight it is converted to its active metabolite to produce a beneficial reaction affecting the diseased tissue.
Mechanism of ActionAfter photoactivation it creates interstrand cross-links in DNA, which can cause programmed cell death.
FDA Pharmacological Classification
Y6UY8OV51T
TRIOXSALEN
Established Pharmacologic Class [EPC] - Psoralen
Chemical Structure [CS] - Psoralens
Trioxsalen is a Psoralen.
MeSH Pharmacological Classification
Drugs that are pharmacologically inactive but when exposed to ultraviolet radiation or sunlight are converted to their active metabolite to produce a beneficial reaction affecting the diseased tissue. These compounds can be administered topically or systemically and have been used therapeutically to treat psoriasis and various types of neoplasms.
Cellular LocationsCytoplasm
Uses & manufacturing
General Manufacturing Information7H-Furo[3,2-g][1]benzopyran-7-one, 2,5,9-trimethyl-: INACTIVE
Applications
Usesmelanizing agent, antipsoriatic
UsesTrioxsalen has been used: to induce small deletion mutations in worms in combination with ultraviolet A (UVA) to induce interstrand crosslinks (ICLs) in DNA for the preparation and photoactivation of trimethyl psoralen
Related reactions
2 records
Compound notes
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