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Melphalan

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Name Melphalan EINECS 205-726-3
CAS No. 148-82-3 Density 1.32 g/cm3
Solubility <0.1 g/100 mL at °C in water Melting Point 180 °C
Formula C13H18Cl2N2O2 Boiling Point 473.1 °C at 760 mmHg
Molecular Weight 305.23 Flash Point 239.9 °C
Transport Information UN 2811 6.1/PG 2 Appearance Crystalline Solid
Safety 53-22-36/37/39-45 Risk Codes 45-46-26/27/28-63
Molecular Structure Molecular Structure of 148-82-3 (Melphalan) Hazard Symbols VeryT+
Synonyms

L-Phenylalanine, 4-[bis (2-chloroethyl)amino]-;{3-p-[Di(2-chloroethyl)amino]} phenyl-L-alanine;SK-15673;Alanine, 3-[p-[bis (2-chloroethyl)amino]phenyl]-, L-;{3-[p-[Bis(2-chloroethyl)amino]phenyl]-L-alanine};

 

Chemistry

Structure of Melphalan (CAS NO.148-82-3):

IUPAC Name: (2S)-2-amino-3-[4-[bis(2-chloroethyl)amino]phenyl]propanoic acid 
Empirical Formula: C13H18Cl2N2O2
Molecular Weight: 305.2002 
EINECS: 205-726-3 
Index of Refraction: 1.596
Molar Refractivity: 78.77 cm3
Molar Volume: 231.2 cm3
Polarizability: 31.22×10-24cm3
Surface Tension: 55.2 dyne/cm
Density: 1.32 g/cm3
Flash Point: 239.9 °C
Enthalpy of Vaporization: 77.55 kJ/mol 
Melting Point: ~180 °C
Boiling Point: 473.1 °C at 760 mmHg
Vapour Pressure: 9.33E-10 mmHg at 25°C 
Water Solubility: <0.1 g/100 mL at 22 ºC 
Physical Appearance: Crystalline Solid
Product Categories: Amino Acids 13C, 2H, 15N;Amino Acids & Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals

Uses

 Melphalan (CAS NO.148-82-3) is used to treat multiple myeloma and ovarian cancer, and occasionally malignant melanoma. The agent was first investigated as a possible drug for use in melanoma. It was not found to be effective, but has been found to be effective in the treatment of myeloma.

Toxicity Data With Reference

1.    

skn-rbt 5 mg/24H rns

    TXCYAC    Toxicology. 14 (1979),117.
2.    

skn-rbt 1 pph/24H MLD

    NTIS**    National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) PB270-483 .
3.    

mmo-sat 100 µg/plate

    ONCODU    Revista de Chirurgui, Oncologie, Radiologie, ORL, Oftalmologie, Stomatologie, Seria: Oncologia. 18 (1979),95.
4.    

dnr-esc 100 µg/disc

    CNREA8    Cancer Research. 34 (1974),1658.
5.    

dnr-esc 100 µg/disc

    CNREA8    Cancer Research. 34 (1974),1658.
6.    

ipr-rat TDLo:70 mg/kg/26W-I:NEO

    RRCRBU    Recent Results in Cancer Research. 52 (1975),1.
7.    

orl-hmn TDLo:700 mg/kg/7D:GIT

    34ZIAG    Toxicology of Drugs and Chemicals ,Deichmann, W.B.,New York, NY.: Academic Press, Inc.,1969,367.
8.    

orl-hmn TDLo:1200 µg/kg/5D-I:GIT

    CCROBU    Cancer Chemotherapy Reports, Part 1. 57 (1973),369.
9.    

ivn-cld LDLo:4500 mg/kg

    NZMJAX    New Zealand Medical Journal. 97 (1984),816.
10.    

ivn-man LDLo:8140 mg/kg

    NZMJAX &n

Consensus Reports

NTP 10th Report on Carcinogens. IARC Cancer Review: Group 1 IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 239.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Sufficient Evidence; Human Limited Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 9 ,1975,p. 167.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . NCI Carcinogenesis Studies (ipr); Clear Evidence: mouse, rat RRCRBU    Recent Results in Cancer Research. 52 (1975),1. . EPA Genetic Toxicology Program.

Safety Profile

Confirmed human carcinogen producing leukemia and Hodgkin′s disease. Poison by ingestion, intravenous, and intracerebral routes. Human systemic effects by ingestion: nausea, hypermotility, diarrhea, agranulocytosis, thrombocytopenia. Human reproductive effects by ingestion: menstrual changes. Mutation data reported. A skin irritant. Used as a poison gas. When heated to decomposition it emits toxic fumes of Cl and NOx.
Hazard Codes: VeryT+
Risk Statements: 45-46-26/27/28-63 
R45:May cause cancer. 
R46:May cause heritable genetic damage. 
R26/27/28:Very toxic by inhalation, in contact with skin and if swallowed. 
R63:Possible risk of harm to the unborn child.
Safety Statements: 53-22-36/37/39-45 
S53:Avoid exposure - obtain special instructions before use. 
S22:Do not breathe dust. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 2811 6.1/PG 2
WGK Germany: 3
RTECS: AY3675000
F: 8
HazardClass: 6.1(a)
PackingGroup: II

Specification

  Melphalan , its cas register number is 148-82-3. It also can be called 3-(p-(Bis(2-chloroethyl)amino)phenyl)-L-alanine ; 4-(Bis(2-chloroethyl)amino)-L-phenylalanine ; Alanine, 3-(p-(bis(2-chloroethyl)amino)phenyl)-, L- ; L-3-(p-(Bis(2-chloroethyl)amino)phenyl)alanine ; L-3-(para-(Bis(2-chloroethyl)amino)phenyl)alanine ; L-Phenylalanine mustard ; L-Sarcolysin ; Phenylalanine mustard ; Phenylalanine nitrogen mustard ; p-Bis(beta-chloroethyl)aminophenylalanine ; p-Di-(2-chloroethyl)amino-L-phenylalanine ; p-L-Sarcolysin ; p-N-Bis(2-chloroethyl)amino-L-phenylalanine .

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