CAS Number148-82-3
Synonyms4-[Bis(2-chloroethyl)amino]-L-phenylalanine; L-3-[p-[Bis(2-chloroethyl)amino]phenyl]alanine; melphalan; 2-Amino-3-[4-[bis(2-chloroethyl)amino]phenyl]propanoic acid; MFCD00057717; (2S)-2-amino-3-{4-[bis(2-chloroethyl)amino]phenyl}propanoic acid; Sarcoclorin; L-Phenylalanine mustard; EINECS 205-726-3; p-Di(2-chloroethyl)amino-L-phenylalanine; 3-(4-bis(2-chloroethyl)aminophenyl)-L-alanine; 3-[p-[Bis(2-chloroethyl)amino]phenyl]-L-alanine
Molecular FormulaC13H18Cl2N2O2
Molecular Weight305.20
Purity97%%
Density1.3±0.1 g/cm3
Boiling Point473.1±45.0 °C at 760 mmHg
Melting Point~180 °C
Appearancepowder
EINECS205-726-3
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 148-82-3 |
| Catalog No. | 2A-9011330 |
| Chinese Name | (+-)-A-甲基-4-羧基苯糖胶 |
| Synonyms | 4-[Bis(2-chloroethyl)amino]-L-phenylalanine; L-3-[p-[Bis(2-chloroethyl)amino]phenyl]alanine; melphalan; 2-Amino-3-[4-[bis(2-chloroethyl)amino]phenyl]propanoic acid; MFCD00057717; (2S)-2-amino-3-{4-[bis(2-chloroethyl)amino]phenyl}propanoic acid; Sarcoclorin; L-Phenylalanine mustard; EINECS 205-726-3; p-Di(2-chloroethyl)amino-L-phenylalanine; 3-(4-bis(2-chloroethyl)aminophenyl)-L-alanine; 3-[p-[Bis(2-chloroethyl)amino]phenyl]-L-alanine |
| Molecular Formula | C13H18Cl2N2O2 |
| Molecular Weight | 305.20 |
| Purity | 97% |
| Density | 1.3±0.1 g/cm3 |
| Boiling Point | 473.1±45.0 °C at 760 mmHg |
| Melting Point | ~180 °C |
| Appearance | powder |
| Water Solubility | 95% ethanol and 1 drop 6 N HCl: 0.05 g/mL, clear | |
| Storage Condition | Store in a dry and cool place. |
| Packaging | II |
| Application | Melphalan is a potent DNA alkylator with anti-tumor activity. |
| EINECS | 205-726-3 |
| HTC | 2922499990 |
| PubChem ID | 24278538 |
| MDL Number | MFCD00057717 |
| SMILES | N[C@@H](Cc1ccc(cc1)N(CCCl)CCCl)C(O)=O |
| InChI | 1S/C13H18Cl2N2O2/c14-5-7-17(8-6-15)11-3-1-10(2-4-11)9-12(16)13(18)19/h1-4,12H,5-9,16H2,(H,18,19)/t12-/m0/s1 |
| InChI Key | SGDBTWWWUNNDEQ-LBPRGKRZSA-N |
| Beilstein/REAXYS | 2816456 |
| NACRES Code | NA.32 |
| UNSPSC | 12352207 |
| Hazard Symbols | 6.1(a) |
| MSDS | msds/11330_1_148_82_3.pdf |
| Use of | Melphalan is an effective DNA alkylating agent, with potent antitumor activity. Properties Articles161 Name melphalan Synonym More Synonyms melphalan Biological Activity Description Melphalan is an effective DNA alkylating agent, with potent antitumor activity. Related Catalog Signaling Pathways >> Cell Cycle/DNA Damage >> DNA Alkylator/Crosslinker Research Areas >> Cancer DNA Alkylator/Crosslinker[1] In Vitro Melphalan is a DNA alkylating agent, used for multiple myeloma[1]. Melphalan-DNA adducts can be visualised in both cultured cells and solid tumour tissue[3]. References [1]. BLUMBERG BS, et al. AN ALKYLATING AGENT FOR MULTIPLE MYELOMA: MELPHALAN. JAMA. 1965 Feb 15;191:547-9. [2]. Glehen O, et al. Hyperthermia modifies pharmacokinetics and tissue distribution of intraperitoneal melphalan in a rat model. Cancer Chemother Pharmacol. 2004 Jul;54(1):79-84. [3]. Rothbarth J, et al. Immunohistochemical detection of melphalan-DNA adducts in colon cancer cells in vitro and human colorectal liver tumours in vivo. Biochem Pharmacol. 2004 May 1;67(9):1771-8. Chemical & Physical Properties Exact Mass 304.074524 PSA 66.56000 Index of Refraction 1.597 InChIKey SGDBTWWWUNNDEQ-LBPRGKRZSA-N Storage condition -20?C Freezer Toxicological Information CHEMICAL IDENTIFICATION RTECS NUMBER : CHEMICAL NAME : Alanine, 3-(p-(bis(2-chloroethyl)amino)phenyl)-, L- CAS REGISTRY NUMBER : BEILSTEIN REFERENCE NO. : LAST UPDATED : DATA ITEMS CITED : MOLECULAR FORMULA : C13-H18-Cl2-N2-O2 MOLECULAR WEIGHT : WISWESSER LINE NOTATION : QVYZ1R DN2G2G -L HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : Rinsed with water ROUTE OF EXPOSURE : Administration onto the skin SPECIES OBSERVED : Rodent - rabbit TYPE OF TEST : Standard Draize test ROUTE OF EXPOSURE : Administration onto the skin SPECIES OBSERVED : Rodent - rabbit TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : SPECIES OBSERVED : DOSE/DURATION : TOXIC EFFECTS : Gastrointestinal - nausea or vomiting TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : SPECIES OBSERVED : DOSE/DURATION : 1200 ug/kg/5D-I TOXIC EFFECTS : Gastrointestinal - nausea or vomiting TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Human - child DOSE/DURATION : TOXIC EFFECTS : Behavioral - anorexia (human) Gastrointestinal - hypermotility, diarrhea Blood - agranulocytosis TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Human - man DOSE/DURATION : TOXIC EFFECTS : Behavioral - anorexia (human) Gastrointestinal - hypermotility, diarrhea Blood - agranulocytosis TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Human - infant DOSE/DURATION : TOXIC EFFECTS : Gastrointestinal - hypermotility, diarrhea Blood - agranulocytosis Blood - thrombocytopenia TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 11200 ug/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 : Intraperitoneal SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 4484 ug/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 : Intravenous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 4100 ug/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 : Intracerebral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD10 - Lethal Dose ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 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 : Intravenous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 20800 ug/kg TOXIC EFFECTS : Behavioral - somnolence (general depressed activity) Blood - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Parenteral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 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 : Unreported SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 29600 ug/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Mammal - dog DOSE/DURATION : TOXIC EFFECTS : Behavioral - somnolence (general depressed activity) Gastrointestinal - hypermotility, diarrhea Blood - normocytic anemia TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : SPECIES OBSERVED : Rodent - rat DOSE/DURATION : TOXIC EFFECTS : Endocrine - changes in spleen weight Immunological Including Allergic - decrease in humoral immune response Nutritional and Gross Metabolic - weight loss or decreased weight gain TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : SPECIES OBSERVED : Human - woman DOSE/DURATION : 80 ug/kg/D-C TOXIC EFFECTS : Tumorigenic - Carcinogenic by RTECS criteria Blood - other changes Blood - lymphoma, including Hodgkin's disease TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : SPECIES OBSERVED : Human - man DOSE/DURATION : 57 ug/kg/D-C TOXIC EFFECTS : Tumorigenic - Carcinogenic by RTECS criteria Blood - other changes Blood - lymphoma, including Hodgkin's disease TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Unreported SPECIES OBSERVED : Human - woman DOSE/DURATION : TOXIC EFFECTS : Tumorigenic - Carcinogenic by RTECS criteria Blood - tumors TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - rat DOSE/DURATION : TOXIC EFFECTS : Tumorigenic - neoplastic by RTECS criteria Tumorigenic - tumors at site of application TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Administration onto the skin SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : TOXIC EFFECTS : Tumorigenic - equivocal tumorigenic agent by RTECS criteria Lungs, Thorax, or Respiration - tumors Skin and Appendages - tumors TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : TOXIC EFFECTS : Tumorigenic - Carcinogenic by RTECS criteria Lungs, Thorax, or Respiration - tumors Blood - lymphoma, including Hodgkin's disease TYPE OF TEST : TD - Toxic dose (other than lowest) ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : TOXIC EFFECTS : Tumorigenic - neoplastic by RTECS criteria Skin and Appendages - tumors TYPE OF TEST : TD - Toxic dose (other than lowest) ROUTE OF EXPOSURE : SPECIES OBSERVED : Human - man DOSE/DURATION : TOXIC EFFECTS : Tumorigenic - Carcinogenic by RTECS criteria Blood - leukemia TYPE OF TEST : TD - Toxic dose (other than lowest) ROUTE OF EXPOSURE : SPECIES OBSERVED : Human - man DOSE/DURATION : TOXIC EFFECTS : Tumorigenic - Carcinogenic by RTECS criteria Blood - leukemia TYPE OF TEST : TD - Toxic dose (other than lowest) ROUTE OF EXPOSURE : SPECIES OBSERVED : Human - woman DOSE/DURATION : TOXIC EFFECTS : Tumorigenic - Carcinogenic by RTECS criteria Blood - leukemia TYPE OF TEST : TD - Toxic dose (other than lowest) ROUTE OF EXPOSURE : SPECIES OBSERVED : Human - woman DOSE/DURATION : TOXIC EFFECTS : Tumorigenic - Carcinogenic by RTECS criteria Blood - leukemia TYPE OF TEST : TD - Toxic dose (other than lowest) ROUTE OF EXPOSURE : SPECIES OBSERVED : Human - man DOSE/DURATION : TOXIC EFFECTS : Tumorigenic - Carcinogenic by RTECS criteria Blood - leukemia TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : 3750 ug/kg SEX/DURATION : female 25 day(s) pre-mating TOXIC EFFECTS : Reproductive - Maternal Effects - menstrual cycle changes or disorders TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Unreported 8800 ug/kg SEX/DURATION : female 1 day(s) pre-mating TOXIC EFFECTS : Reproductive - Maternal Effects - ovaries, fallopian tubes Reproductive - Maternal Effects - other effects TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Unreported 5946 ug/kg SEX/DURATION : female 1 day(s) pre-mating TOXIC EFFECTS : Reproductive - Maternal Effects - menstrual cycle changes or disorders TYPE OF TEST : Specific locus test TYPE OF TEST : Specific locus test TYPE OF TEST : Sex chromosome loss and nondisjunction TYPE OF TEST : Micronucleus test TYPE OF TEST : Specific locus test TYPE OF TEST : DNA damage TYPE OF TEST : Unscheduled DNA synthesis TYPE OF TEST : DNA inhibition TYPE OF TEST : Sister chromatid exchange TYPE OF TEST : Dominant lethal test TYPE OF TEST : Heritable translocation test MUTATION DATA TYPE OF TEST : DNA damage TEST SYSTEM : Mammal - species unspecified Lymphocyte DOSE/DURATION : 2500 nmol/L REFERENCE : MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 368,235,1996 *** REVIEWS *** IARC Cancer Review:Human Sufficient Evidence IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,239,1987 IARC Cancer Review:Animal Sufficient 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: 9,167,1975 IARC Cancer Review:Group 1 IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,239,1987 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X4742 No. of Facilities: 140 (estimated) No. of Industries: 1 No. of Occupations: 4 No. of Employees: 2418 (estimated) No. of Female Employees: 974 (estimated) Safety Information GHS06, GHS08 Signal Word Danger Hazard Statements H300-H310-H330-H350-H361 Precautionary Statements P201-P260-P264-P280-P284-P302 + P350 Personal Protective Equipment Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges Hazard Codes T+:Verytoxic; WGK Germany 3 RTECS AY3675000 Packaging Group II Hazard Class 6.1(a) HS Code 2922499990 Synthetic Route Total: 1 Page methyl 2-amino-... CAS#:62978-52-3 CAS#:148-82-3 N-Boc-4-[bis(2-... CAS#:1217651-06-3 CAS#:148-82-3 Precursor & DownStream Precursor 2 CAS#:62978-52-3 methyl 2-amino-... CAS#:1217651-06-3 N-Boc-4-[bis(2-... DownStream 2 CAS#:35849-41-3 l-3-(p-(BIS(2-C... CAS#:62978-52-3 methyl 2-amino-... |
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