Product Name

  • Name

    Carmustine

  • EINECS 205-838-2
  • CAS No. 154-93-8
  • Article Data13
  • CAS DataBase
  • Density 1.46 g/cm3
  • Solubility water: <0.1 g/100 mL at 18 °C
  • Melting Point 30 °C(lit.)
  • Formula C5H9Cl2N3O2
  • Boiling Point 404oC
  • Molecular Weight 214.051
  • Flash Point
  • Transport Information
  • Appearance light yellow powder
  • Safety 53-22-36/37/39-45
  • Risk Codes 45-46-60-61-28
  • Molecular Structure Molecular Structure of 154-93-8 (Carmustine)
  • Hazard Symbols VeryT+
  • Synonyms Urea,1,3-bis(2-chloroethyl)-1-nitroso- (8CI);1,3-Bis(b-chloroethyl)-1-nitrosourea;BCNU;Becenun;BiCNU;DTI 015;FDA 0345;Gliadel;Gliadel Wafer;N,N'-Bis(2-chloroethyl)-N-nitrosourea;NSC 409962;Nitrumon;SK 27702;SRI 1720;
  • PSA 61.77000
  • LogP 1.54790

Synthetic route

1,3-bis(2-chloroethyl)urea
2214-72-4

1,3-bis(2-chloroethyl)urea

1,3-bis(2-chloroethyl)-1-nitrosourea
154-93-8

1,3-bis(2-chloroethyl)-1-nitrosourea

Conditions
ConditionsYield
With tin(IV) chloride; sodium nitrite In dichloromethane at 20℃; for 2h;100%
With formic acid; sodium nitrite In dichloromethane; water at 0 - 3℃; for 1h;87%
With formic acid; sodium nitrite
1,2,2,2-Tetrachloroethyl N-(2-chloroethyl) N-nitroso-carbamate
113900-20-2

1,2,2,2-Tetrachloroethyl N-(2-chloroethyl) N-nitroso-carbamate

chloroethylamine
689-98-5

chloroethylamine

1,3-bis(2-chloroethyl)-1-nitrosourea
154-93-8

1,3-bis(2-chloroethyl)-1-nitrosourea

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran for 2h; Ambient temperature; Yield given;
1,3-bis(2-chloroethyl)-1-nitrosourea
154-93-8

1,3-bis(2-chloroethyl)-1-nitrosourea

A

ethylene glycol
107-21-1

ethylene glycol

B

acetaldehyde
75-07-0

acetaldehyde

C

2-chloro-ethanol
107-07-3

2-chloro-ethanol

Conditions
ConditionsYield
With sodium phosphate buffer at 37℃; for 96h; Product distribution; Mechanism; other nitrosoureas; var. pH, also in the presence of KBr;A 2%
B 19%
C 51%
...Expand
1,3-bis(2-chloroethyl)-1-nitrosourea
154-93-8

1,3-bis(2-chloroethyl)-1-nitrosourea

A

1,3-bis(2-chloroethyl)urea
2214-72-4

1,3-bis(2-chloroethyl)urea

B

2-<(2-chloroethyl)amino>-2-oxazoline
71353-16-7

2-<(2-chloroethyl)amino>-2-oxazoline

C

1-(2-chloroethyl)imidazolidin-2-one
2387-20-4

1-(2-chloroethyl)imidazolidin-2-one

D

ethanol
64-17-5

ethanol

E

ethylamine
75-04-7

ethylamine

Conditions
ConditionsYield
With potassium hydroxide; aluminum nickel In methanol Product distribution; Mechanism; degradation under various conditions (HBr in glac. CH3CO2H) with preparation of nonmutagenic reaction mixtures of products;
...Expand
1,3-bis(2-chloroethyl)-1-nitrosourea
154-93-8

1,3-bis(2-chloroethyl)-1-nitrosourea

ethanol
64-17-5

ethanol

Conditions
ConditionsYield
With equine liver alcohol dehydrogenase; 1,4-dihydronicotinamide adenine dinucleotide; potassium phoshpate buffer; water at 25℃; for 12h; Mechanism; the other reagent ; other 1H- and 18O-labeled 1-nitrosoureas;
1,3-bis(2-chloroethyl)-1-nitrosourea
154-93-8

1,3-bis(2-chloroethyl)-1-nitrosourea

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

1,3-Bis-(2-chloro-ethyl)-1,3-bis-(2,2,2-trifluoro-acetyl)-urea

1,3-Bis-(2-chloro-ethyl)-1,3-bis-(2,2,2-trifluoro-acetyl)-urea

Conditions
ConditionsYield
at 85℃; for 6h;
glutathione
35436-84-1

glutathione

1,3-bis(2-chloroethyl)-1-nitrosourea
154-93-8

1,3-bis(2-chloroethyl)-1-nitrosourea

A

S-(2-chloroethyl)glutathione

S-(2-chloroethyl)glutathione

B

(S)-4-[(R)-1-(Carboxymethyl-carbamoyl)-2-mercapto-ethylcarbamoyl]-4-(2-chloro-ethylamino)-butyric acid

(S)-4-[(R)-1-(Carboxymethyl-carbamoyl)-2-mercapto-ethylcarbamoyl]-4-(2-chloro-ethylamino)-butyric acid

C

S-glutathione

S-glutathione

D

N,S-bis-glutathione

N,S-bis-glutathione

Conditions
ConditionsYield
With phosphate buffer at 37℃; for 3h; pH 7.4; Further byproducts given. Title compound not separated from byproducts;
With phosphate buffer at 37℃; for 3h; pH 7.4; Further byproducts given;
...Expand
glutathione
35436-84-1

glutathione

1,3-bis(2-chloroethyl)-1-nitrosourea
154-93-8

1,3-bis(2-chloroethyl)-1-nitrosourea

A

S-(2-chloroethyl)glutathione

S-(2-chloroethyl)glutathione

B

(S)-4-[(R)-1-(Carboxymethyl-carbamoyl)-2-mercapto-ethylcarbamoyl]-4-(2-chloro-ethylamino)-butyric acid

(S)-4-[(R)-1-(Carboxymethyl-carbamoyl)-2-mercapto-ethylcarbamoyl]-4-(2-chloro-ethylamino)-butyric acid

C

S-glutathione

S-glutathione

D

(S)-4-Amino-4-[(R)-2-{2-[(R)-2-((S)-2-amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-ethylsulfanyl}-1-(carboxymethyl-carbamoyl)-ethylcarbamoyl]-butyric acid

(S)-4-Amino-4-[(R)-2-{2-[(R)-2-((S)-2-amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-ethylsulfanyl}-1-(carboxymethyl-carbamoyl)-ethylcarbamoyl]-butyric acid

Conditions
ConditionsYield
With phosphate buffer at 37℃; for 3h; pH 7.4; Further byproducts given;
...Expand
1,3-bis(2-chloroethyl)-1-nitrosourea
154-93-8

1,3-bis(2-chloroethyl)-1-nitrosourea

A

S-cysteinylglycine

S-cysteinylglycine

B

(S)-4-Amino-4-[(R)-1-(carboxymethyl-carbamoyl)-2-((E)-2-chloro-vinylcarbamoylsulfanyl)-ethylcarbamoyl]-butyric acid

(S)-4-Amino-4-[(R)-1-(carboxymethyl-carbamoyl)-2-((E)-2-chloro-vinylcarbamoylsulfanyl)-ethylcarbamoyl]-butyric acid

C

S-glutathione

S-glutathione

D

(S)-4-Amino-4-[(R)-1-(carboxymethyl-carbamoyl)-2-(4,5-dihydro-oxazol-2-ylsulfanyl)-ethylcarbamoyl]-butyric acid

(S)-4-Amino-4-[(R)-1-(carboxymethyl-carbamoyl)-2-(4,5-dihydro-oxazol-2-ylsulfanyl)-ethylcarbamoyl]-butyric acid

Conditions
ConditionsYield
for 4h; Product distribution; Mechanism; rat's liver; also in vitro with glutathione at 37 deg C inphosphate buffer;
...Expand
1,3-bis(2-chloroethyl)-1-nitrosourea
154-93-8

1,3-bis(2-chloroethyl)-1-nitrosourea

L-ornithine hydrochloride
3184-13-2

L-ornithine hydrochloride

Nδ-nitroso-Nδ-(2-chloroethyl)carbamoyl-L-ornithine; Nδ-(2-chloroethyl)nitrosocarbamoyl-L-ornithine; mixture of

Nδ-nitroso-Nδ-(2-chloroethyl)carbamoyl-L-ornithine; Nδ-(2-chloroethyl)nitrosocarbamoyl-L-ornithine; mixture of

Conditions
ConditionsYield
Stage #1: 1,3-bis(2-chloroethyl)-1-nitrosourea; L-ornithine hydrochloride With potassium hydroxide; copper(II) sulfate In water; isopropyl alcohol at 32℃; for 1h; Alkylation;
Stage #2: With sodium nitrite In water at 0℃; for 1h; Nitrosation;		4.21 g
1,3-bis(2-chloroethyl)-1-nitrosourea
154-93-8

1,3-bis(2-chloroethyl)-1-nitrosourea

D-ornithine hydrochloride
16682-12-5

D-ornithine hydrochloride

Nδ-nitroso-Nδ-(2-chloroethyl)carbamoyl-D-ornithine; Nδ-(2-chloroethyl)nitrosocarbamoyl-D-ornithine; mixture of

Nδ-nitroso-Nδ-(2-chloroethyl)carbamoyl-D-ornithine; Nδ-(2-chloroethyl)nitrosocarbamoyl-D-ornithine; mixture of

Conditions
ConditionsYield
Stage #1: 1,3-bis(2-chloroethyl)-1-nitrosourea; D-ornithine hydrochloride With potassium hydroxide; copper(II) sulfate In water; isopropyl alcohol at 32℃; for 1h; Alkylation;
Stage #2: With sodium nitrite In water at 0℃; for 1h; Nitrosation;		6.25 g
1,3-bis(2-chloroethyl)-1-nitrosourea
154-93-8

1,3-bis(2-chloroethyl)-1-nitrosourea

L-Lysine hydrochloride
657-27-2, 10098-89-2

L-Lysine hydrochloride

Nε-nitroso-Nε-(2-chloroethyl)carbamoyl-L-lysine; Nε-(2-chloroethyl)nitrosocarbamoyl-L-lysine; mixture of

Nε-nitroso-Nε-(2-chloroethyl)carbamoyl-L-lysine; Nε-(2-chloroethyl)nitrosocarbamoyl-L-lysine; mixture of

Conditions
ConditionsYield
Stage #1: 1,3-bis(2-chloroethyl)-1-nitrosourea; L-Lysine hydrochloride With potassium hydroxide; copper(II) sulfate In water; isopropyl alcohol at 32℃; for 1h; Alkylation;
Stage #2: With sodium nitrite In water at 0℃; for 1h; Nitrosation;		9.7 g
1,3-bis(2-chloroethyl)-1-nitrosourea
154-93-8

1,3-bis(2-chloroethyl)-1-nitrosourea

diethyl 1-aminoethyl phosphate

diethyl 1-aminoethyl phosphate

C9H20ClN2O5P

C9H20ClN2O5P

Conditions
ConditionsYield
In water at 60℃; for 2h; Concentration;

Carmustin Chemical Properties

Product Name: Carmustin (CAS NO.154-93-8)
IUPAC Name: 1,3-bis(2-chloroethyl)-1-nitrosourea

MF: C5H9Cl2N3O2                                 
MW: 214.05
Apperance: orange-yellow solid
EINECS: 205-838-2
Mol File: 154-93-8.mol
Surface Tension: 50.3 dyne/cm 
Density: 1.46 g/ml
MP: 30 °C(lit.)
Water Solubility: <0.1 g/100 mL at 18 °C
Index of Refraction: 1.548 
Molar Refractivity: 46.55 cm3 
Molar Volume: 146.4 cm3   
Surface Tension: 50.3 dyne/cm
Product Categories: Active Pharmaceutical Ingredients; Pharmaceutical Chemicals; Mutagenesis Research Chemicals

Carmustin Uses

 The Carmustin(CAS NO.154-93-8) is used as the goods for the broad-spectrum anti-cancer drug.It has a good effect on the breast, lung, brain and cancer, bone metastases, also have a certain effect for Hodgkin's Disease and acute leukemia.

Carmustin Toxicity Data With Reference

1.    

mmo-sat 33 µg/plate

     TCMUD8    Teratogenesis, Carcinogenesis, and Mutagenesis. 5 (1985),319.
2.    

sce-hmn:lym 25 µmol/L

     CNREA8    Cancer Research. 45 (1985),4798.
3.    

ivn-cld LDLo:78 mg/kg/52W I

     CANCAR    Cancer. 42 (1978),74.
4.    

ivn-hmn TDLo:125 mg/kg:BLD,GIT

     ACRSAJ    Advances in Cancer Research. 16 (1972),273.
5.    

ivn-hmn TDLo:6 mg/kg:BLD,GIT

     CTRRDO    Cancer Treatment Reports. 60 (1976),709.
6.    

par-wmn LDLo:1566 mg/kg:PUL

     JAMAAP    JAMA, Journal of the American Medical Association. 244 (1980),687.
7.    

orl-rat LD50:20 mg/kg

     JPETAB    Journal of Pharmacology and Experimental Therapeutics. 166 (1969),104.
8.    

ipr-rat LD50:17,420 µg/kg

     NCISP*    National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program, Bethesda, MD 20205 JAN86 .
9.    

scu-rat LD50:83,200 µg/kg

     IYKEDH    Iyakuhin Kenkyu. Study of Medical Supplies. 9 (1978),766.
10.    

ivn-rat LD50:13,800 µg/kg

     ONCOBS    Oncology. 37 (1980),177.

Carmustin Consensus Reports

NTP 10th Report on Carcinogens. IARC Cancer Review: Group 2A IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man 7 (1987),p. 150.(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) ; Human Limited Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man 26 (1981),p. 79.(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 IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man 26 (1981),p. 79.(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); Some Evidence: rat CANCAR    Cancer. 40 (1977),1935. ; Clear Evidence: mouse CANCAR    Cancer. 40 (1977),1935. . EPA Genetic Toxicology Program.

Carmustin Safety Profile

Confirmed carcinogen with experimental carcinogenic and tumorigenic data. A human poison by parenteral route. An experimental poison by ingestion, intravenous, intraperitoneal, parenteral, and subcutaneous routes. Human systemic effects by parenteral, intravenous, and possibly other routes: nausea or vomiting, reduced white blood cell and blood platelet counts, bone marrow damage, and potentially fatal respiratory system effects including lung fibrosis, dyspnea, and cyanosis. Experimental teratogenic and reproductive effects. Human mutation data reported. When heated to decomposition it emits very toxic fumes of Cl− and NOx. See also N-NITROSO COMPOUNDS.
Safety information of Carmustin (CAS NO.154-93-8):
Hazard Codes: T+
Risk Statements: 45-46-60-61-28
R45:May cause cancer ;
R46:May cause heritable genetic damage ;
R60:May impair fertility ;
R61:May cause harm to the unborn child ;
R28:Very Toxic if swallowed ;
Safety Statements: 53-22-36/37/39-45
S53:Avoid exposure - obtain special instruction 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 label where possible) ;
RIDADR: 3249
WGK Germany: 3
RTECS: YS2625000
HazardClass: 6.1(a)
PackingGroup: II

Carmustin Specification

 Carmustin, its CAS NO. is 154-93-8, the synonyms are 1,3-Bis(2-chloroethyl)-1-nitrosourea ; 1,3-Bis(2-chloroethyl)nitrosourea ; 1,3-Bis(beta-chloroethyl)-1-nitrosourea ; Bis(2-chloroethyl)1-nitrosourea ; Bis(2-chloroethyl)nitrosourea ; Bis-N,N'-(chloroethyl)nitrosourea ; Bischlorethylnitrosourea ; Bischlorethylnitrosurea ; Bischloroethyl nitrosourea ; Bischloroethylnitrosourea .

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