Mechlorethamine HCl
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MedKoo CAT#: 100560

CAS#: 55-86-7 (HCl)

Description: Mechlorethamine, an antineoplastic nitrogen mustard also known as HN2 hydrochloride, is a nitrogen analog of sulfur mustard. It is a light yellow brown, crystalline, hygroscopic powder that is very soluble in water and also soluble in alcohol. (Source: http://www.rxlist.com/mustargen-drug.htm).


Chemical Structure

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Mechlorethamine HCl
CAS# 55-86-7 (HCl)

Theoretical Analysis

MedKoo Cat#: 100560
Name: Mechlorethamine HCl
CAS#: 55-86-7 (HCl)
Chemical Formula: C5H12Cl3N
Exact Mass:
Molecular Weight: 192.51448
Elemental Analysis: C, 31.19; H, 6.28; Cl, 55.25; N, 7.28

Price and Availability

Size Price Availability Quantity
1.0g USD 150.0 2 Weeks
2.0g USD 250.0 2 Weeks
5.0g USD 450.0 2 Weeks
10.0g USD 650.0 2 Weeks
25.0g USD 1050.0 2 Weeks
50.0g USD 1950.0 2 Weeks
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Related CAS #: 51-75-2 (free base)   55-86-7 (HCl)  

Synonym: chloramin; chlorethamine HCl; chlorethamine hydrochloride

IUPAC/Chemical Name: 2-chloro-N-(2-chloroethyl)-N-methylethanamine hydrochloride

InChi Key: QZIQJVCYUQZDIR-UHFFFAOYSA-N

InChi Code: InChI=1S/C5H11Cl2N.ClH/c1-8(4-2-6)5-3-7;/h2-5H2,1H3;1H

SMILES Code: ClCCN(CCCl)C.[H]Cl

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 192.51448 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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 1: Sharma M, Vijayaraghavan R, Gautam A. DRDE-07 and its analogues as promising cytoprotectants to nitrogen mustard (HN-2)--an alkylating anticancer and chemical warfare agent. Toxicol Lett. 2009 Aug 10;188(3):243-50. Epub 2009 May 3. PubMed PMID: 19397960.

2: Armand JP, Ribrag V, Harrousseau JL, Abrey L. Reappraisal of the use of procarbazine in the treatment of lymphomas and brain tumors. Ther Clin Risk Manag. 2007 Jun;3(2):213-24. PubMed PMID: 18360630; PubMed Central PMCID: PMC1936303.

3: Bartzatt R. Alkylation activity and molecular properties of two antineoplastic agents that utilise indometacin and a conjugate of aspirin with 2-aminonicotinic acid to transport nitrogen mustard groups. Drugs R D. 2007;8(6):363-72. PubMed PMID: 17963427.

4: Zhang X, Ling MT, Wong YC, Wang X. Evidence of a novel antiapoptotic factor: role of inhibitor of differentiation or DNA binding (Id-1) in anticancer drug-induced apoptosis. Cancer Sci. 2007 Mar;98(3):308-14. PubMed PMID: 17214747.

5: He D, Zhang D, Wei G, Lin T, Li X. Cytoskeleton vimentin disruption of mouse sertoli cells injured by nitrogen mustard in vitro. J Androl. 2007 May-Jun;28(3):389-96. Epub 2006 Dec 27. PubMed PMID: 17192600.

6: Dutta S, Abe H, Aoyagi S, Kibayashi C, Gates KS. DNA damage by fasicularin. J Am Chem Soc. 2005 Nov 2;127(43):15004-5. PubMed PMID: 16248621.

7: Eklund JW, Trifilio S, Mulcahy MF. Chemotherapy dosing in the setting of liver dysfunction. Oncology (Williston Park). 2005 Jul;19(8):1057-63; discussion 1063-4, 1069. Review. PubMed PMID: 16131047.

8: Guo CC, Tong RB, Li KL. Chloroalkyl piperazine and nitrogen mustard porphyrins: synthesis and anticancer activity. Bioorg Med Chem. 2004 May 1;12(9):2469-75. PubMed PMID: 15080942.

9: Rapp M, Giraud I, Maurizis JC, Galmier MJ, Madelmont JC. Synthesis and in vivo biodisposition of [14C]-quaternary ammonium-melphalan conjugate, a potential cartilage-targeted alkylating drug. Bioconjug Chem. 2003 Mar-Apr;14(2):500-6. PubMed PMID: 12643763.

10: Kapuscinski J, Ardelt B, Piosik J, Zdunek M, Darzynkiewicz Z. The modulation of the DNA-damaging effect of polycyclic aromatic agents by xanthines. Part I. Reduction of cytostatic effects of quinacrine mustard by caffeine. Biochem Pharmacol. 2002 Feb 15;63(4):625-34. PubMed PMID: 11992630.



Additional Information

mechlorethamine hydrochloride is the hydrochloride salt of mechlorethamine, a nitrogen mustard and an analogue of sulfur mustard, with antineoplastic and immunosuppressive activities. Mechlorethamine is metabolized to an unstable, highly reactive ethyleniminium intemediate that alkylates DNA, particularly the 7 nitrogen of guanine residues, resulting in DNA base pair mismatching, DNA interstrand crosslinking, the inhibition of DNA repair and synthesis, cell-cycle arrest, and apoptosis. This agent also exhibits lympholytic properties. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus)
 
History
Successful clinical use of mechlorethamine gave birth to the field of anticancer chemotherapy. The drug is an analogue of mustard gas and was derived from chemical warfare research, in particular a 1943 accident in Bari, Italy which exposed civilians and soldiers-- it was noted that white cell counts of exposed patients decreased, suggesting a possible therapy for the cancer Hodgkin's lymphoma.
 
DRUG DESCRIPTION
MUSTARGEN, an antineoplastic nitrogen mustard also known as HN2 hydrochloride, is a nitrogen analog of sulfur mustard. It is a light yellow brown, crystalline, hygroscopic powder that is very soluble in water and also soluble in alcohol. Mechlorethamine hydrochloride is designated chemically as 2-chloro-N-(2-chloroethyl)-N-methylethanamine hydrochloride. The molecular weight is 192.52 and the melting point is 108-111°C. The empirical formula is C5H11Cl2N•HCl, and the structural formula is: CH3N(CH2CH2Cl)2•HCl. Trituration of MUSTARGEN is a sterile, light yellow brown crystalline powder for injection by the intravenous or intracavitary routes after dissolution. Each vial of MUSTARGEN contains 10 mg of mechlorethamine hydrochloride triturated with sodium chloride q.s. 100 mg. When dissolved with 10 mL Sterile Water for Injection or 0.9% Sodium Chloride Injection, the resulting solution has a pH of 3-5 at a concentration of 1 mg mechlorethamine HCl per mL.