Xanthotoxin

Names

[ CAS No. ]:
298-81-7

[ Name ]:
Xanthotoxin

[Synonym ]:
8-MP
Puvalen
Xanthotoxin
Methoxsalen
Puvamet
Dermox
Meloxine
7H-Furo[3,2-g][1]benzopyran-7-one, 9-methoxy-
Vitpso
Meladinine
Deltasoralen
OXSORALEN
9-methoxypsoralen
8-methoxypsoralene
8-MOP,9-Methoxyfuro[3,2-g][1]benzopyran-7-one,Ammoidin
Uvadex
9-Methoxy-7H-furo[3,2-g]chromen-7-one
Ammodin
8-MOP
8-MOP,8-Methoxypsoralen,9-Methoxyfuro[3,2-g][1]benzopyran-7-one
EINECS 206-066-9
Methoxsalen, 8-
6-Hydroxy-7-methoxy-5-benzofuranacrylic Acid d-Lactone
MFCD00005009
8-Methoxypsoralen
Metoxin
8-Methoxy[furano-3',2':6,7-coumarin]

Biological Activity

[Description]:

Methoxsalen (8-Methoxypsoralen) is a potent tricyclic furocoumarin suicide inhibitor of CYP (cytochrome P-450), is an agent used to treat psoriasis, eczema, vitiligo and some cutaneous Lymphomas in conjunction with exposing the skin to sunlight.Target: CYP (cytochrome P-450)Methoxsalen is a drug used to treat psoriasis, eczema, vitiligo, and some cutaneous lymphomas in conjunction with exposing the skin to UVA light from lamps or sunlight. Methoxsalen modifies the way skin cells receive the UVA radiation, allegedly clearing up the disease. The dosage comes in 10 mg tablets, which are taken in the amount of 30 mg 75 minutes before a PUVA (psoralen + UVA) light treatment. Chemically, methoxsalen belongs to a class of organic natural molecules known asfuranocoumarins. They consist of coumarin annulated with furan.Administration of intra peritoneal (ip) methoxsalen significantly increased nicotine's Cmax, prolonged the plasma half-life (fourfold decrease) of nicotine, and increased its area under the curve (AUC) compared with ip vehicle treatment. Methoxsalen pretreatment prolonged the duration of nicotine-induced antinociception and hypothermia (15mg/kg, po) for periods up to 6- and 24-hr postnicotine administration, respectively.

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Cytochrome P450

Natural Products >> Phenylpropanoids

Research Areas >> Inflammation/Immunology

[References]

[1]. Alsharari SD, et al. Pharmacokinetic and Pharmacodynamics Studies of Nicotine After Oral Administration in Mice: Effects of Methoxsalen, a CYP2A5/6 Inhibitor. Nicotine Tob Res. 2014 Jan;16(1):18-25.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
414.8±45.0 °C at 760 mmHg

[ Melting Point ]:
143-148 ºC

[ Molecular Formula ]:
C₁₂H₈O₄

[ Molecular Weight ]:
216.189

[ Flash Point ]:
204.7±28.7 °C

[ Exact Mass ]:
216.042252

[ PSA ]:
52.58000

[ LogP ]:
1.93

[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C

[ Index of Refraction ]:
1.635

[ Storage condition ]:
-20°C Freezer, Under Inert Atmosphere

[ Water Solubility ]:
PRACTICALLY INSOLUBLE

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: LV1400000

CHEMICAL NAME :: 7H-Furo(3,2-g)(1)benzopyran-7-one, 9-methoxy-

CAS REGISTRY NUMBER :: 298-81-7

BEILSTEIN REFERENCE NO. :: 0196453

LAST UPDATED :: 199806

DATA ITEMS CITED :: 40

MOLECULAR FORMULA :: C12-H8-O4

MOLECULAR WEIGHT :: 216.20

WISWESSER LINE NOTATION :: T C566 DO LVOJ BO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 791 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - changes in motor activity (specific assay) Behavioral - ataxia

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 158 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1880 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 423 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - changes in motor activity (specific assay) Behavioral - ataxia

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 250 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - changes in motor activity (specific assay) Behavioral - ataxia

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 860 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 505 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 26 gm/kg/13W-I

TOXIC EFFECTS :: Liver - other changes Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2400 mg/kg/16D-I

TOXIC EFFECTS :: Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 690 mg/kg/15D-I

TOXIC EFFECTS :: Gastrointestinal - hypermotility, diarrhea Liver - hepatitis (hepatocellular necrosis), zonal Blood - hemorrhage

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: 1404 mg/kg/26W-I

TOXIC EFFECTS :: Gastrointestinal - nausea or vomiting

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 18025 mg/kg/2Y-C

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Kidney, Ureter, Bladder - Kidney tumors Sense Organs and Special Senses (Olfaction) - tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 800 mg/kg

SEX/DURATION :: female 6-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1600 mg/kg

SEX/DURATION :: female 6-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1600 mg/kg

SEX/DURATION :: female 6-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous System

MUTATION DATA

TYPE OF TEST :: Sister chromatid exchange

TEST SYSTEM :: Rodent - hamster Ovary

DOSE/DURATION :: 33300 ug/L

REFERENCE :: NTPTR* National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No.206- Volume(issue)/page/year: NTP-TR-359,1989 *** REVIEWS *** IARC Cancer Review:Human Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 24,101,1980 IARC Cancer Review:Animal Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 24,101,1980 TOXICOLOGY REVIEW CRTXB2 CRC Critical Reviews in Toxicology. (CRC Press, Inc., 2000 Corporate Blvd., NW, Boca Raton, FL 33431) V.1- 1971- Volume(issue)/page/year: 1(1),93,1971

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H317

[ Precautionary Statements ]:
P280-P301 + P312 + P330

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Faceshields;Gloves

[ Hazard Codes ]:
T:Toxic

[ Risk Phrases ]:
R22;R34;R45;R46

[ Safety Phrases ]:
S36/37-S53-S45-S36/37/39-S26

[ RIDADR ]:
3216

[ WGK Germany ]:
3

[ RTECS ]:
LV1400000

[ Packaging Group ]:
I; II; III

[ Hazard Class ]:
6.1

[ HS Code ]:
2932999099

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2932999099

[ Summary ]:
2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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Related Compounds

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