CID 6918992

Base Information

• Chemical Name: CID 6918992
• CAS No.: 148-82-3
• Molecular Formula: C13H18Cl2N2O2
• Molecular Weight: 305.204
• Hs Code.: 29224999
• Mol file: 148-82-3.mol

Synonyms:

Chemical Property of CID 6918992

Chemical Property:

• Appearance/Colour: Crystalline Solid
• Melting Point: 180 °C
• Refractive Index: 1.6070 (estimate)
• Boiling Point: 473.1 °C at 760 mmHg
• PKA: pKa 1.42/2.75/9.17(H2O,t =37.0,I=0.5) (Uncertain)
• Flash Point: 239.9 °C
• PSA: 66.56000
• Density: 1.32 g/cm³
• LogP: 2.62530
• Storage Temp.: -20?C Freezer
• Solubility.: 95% ethanol and 1 drop 6 N HCl: 0.05 g/mL, clear
• Water Solubility.: <0.1 g/100 mL at 22℃
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 304.0745332
• Heavy Atom Count: 19
• Complexity: 260

Purity/Quality:

Melphalan ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+
• Statements: 45-46-26/27/28-63-36/38-62
• Safety Statements: 53-22-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1CC(C(=O)[O-])[NH3+])N(CCCl)CCCl
• Isomeric SMILES: C1=CC(=CC=C1C[C@@H](C(=O)[O-])[NH3+])N(CCCl)CCCl
• Description: Melphalan is a nitrogen mustard derivative of the large neutral amino acid L-phenylalanine. It was first synthesized in 1953 by Bergel and Stock and is the active L-isomer of the compound. The D-isomer, known as medphalan, is less active against certain animal tumors, and the dose needed to produce effects on chromosomes is larger than that required with the L-isomer. The racemic (DL-) form is known as merphalan or sarcolysin. Melphalan is a phenylalanine derivative of mechlorethamine, belonging to the family of nitrogen mustard alkylating agents that are used for chemotherapy. It attaches an alkyl group to guanine bases in DNA at the 7-nitrogen of the imidazole ring, which leads to DNA interstrand and intrastrand crosslinks, cytotoxicity, and apoptosis. Melphalan can inhibit the growth of PC-3 prostate cancer cells with IC50 values of 0.074 or 0.77 μM for sequential dosing or single dosing, respectively.
• Uses: Melphalan USP (Alkeran) is used to treat multiple myeloma; plasmacytic myeloma; cancer of breast and ovary. antineoplastic, alkylating agent Glucocorticoid
• Indications: Melphalan (Alkeran) is an amino acid derivative of mechlorethamine that possesses the same general spectrum of antitumor activity as do the other nitrogen mustards. However, the bioavailability of the oral preparation is quite variable (25–90%) from one patient to another. The major indications for melphalan are in the palliative therapy of multiple myeloma and cancers of the breast or ovary. Because it does not produce alopecia, melphalan is occasionally substituted for cyclophosphamide in the CMF regimen for breast cancer. Melphalan produces less nausea and vomiting than does cyclophosphamide; however, its bone marrow suppression tends to be more prolonged and affects both white cells and platelets. Peak suppression of blood counts occurs 14 to 21 days after a 5-day course of drug therapy; recovery is generally complete within 3 to 5 weeks.
• Therapeutic Function: Cancer chemotherapy
• Clinical Use: This aromatic mustard, used primarily in the treatment of multiple myeloma, is able to stabilize the lone pair of electrons on the mustard nitrogen through resonance with the conjugated phenyl ring, slowing the formation of the reactive aziridinium ion.

Technology Process of CID 6918992

There total 8 articles about CID 6918992 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

melphalan methyl ester hydrochloride salt (62978-52-3) → L-PAM (148-82-3,8057-25-8)

Guidance literature:

melphalan methyl ester hydrochloride salt; With hydrogenchloride; water; at 80 - 85 ℃;

With ammonia; In water; at 0 ℃; pH=6;

Reference yield:

melphalan hydrochloride (3223-07-2,4213-32-5) → L-PAM (148-82-3,8057-25-8)

Guidance literature:

With sodium hydrogencarbonate; In water; at 0 - 5 ℃; for 1h; pH=3-5;

Reference yield:

N-(tert-butyloxycarbonyl)-4-(bis(2-chloroethyl)amino)-L-phenylalanine ethyl ester (189744-28-3) → L-PAM (148-82-3,8057-25-8)

Guidance literature:

N-(tert-butyloxycarbonyl)-4-(bis(2-chloroethyl)amino)-L-phenylalanine ethyl ester; With hydrogenchloride; water; In Isopropyl acetate; for 12h; Reflux;

With diethylamine; In tert-butyl methyl ether; water; pH=2;

upstream raw materials:

melphalan methyl ester hydrochloride salt

N-(t-butyloxycarbonyl)-4-[bis(2-hydroxyethyl)amino]-L-phenylalanine methyl ester

(S)-3-(4-aminophenyl)-2-tert-butoxycarbonylamino-propionic acid ethyl ester

N-boc-L-3-(4-bis(hydroxyethyl)aminophenyl)alanine ethyl ester

Downstream raw materials:

melphalan methyl ester hydrochloride salt

N-((tert-butoxy)carbonyl)-4-(bis(2-chloroethyl)amino)-L-phenylalanine

N-(benzyloxycarbonyl)melphalan

melphalan benzyl ester hydrochloride salt

Refernces

• 1、 Wade,Murthy. "". . p. 2564. Retrieved 1968.
• 2、 -. "PROCESS FOR THE PURIFICATION OF MELPHALAN". . . Retrieved 2014/12/12.