2,5-Cyclohexadiene-1,4-dione,2,3,5-tri-1-aziridinyl-

Names

[ CAS No. ]:
68-76-8

[ Name ]:
2,5-Cyclohexadiene-1,4-dione,2,3,5-tri-1-aziridinyl-

[Synonym ]:
Trenimon
Triethyleneiminobenzoquinone
Riker 601
Oncoredox
2,3,5-tris(aziridin-1-yl)cyclohexa-2,5-diene-1,4-dione
Triaziquinone
Prenimon
Treninon
2.3.5-Tris-aziridino-benzo-1.4-chinon
Oncovedex
Triaziquon

Biological Activity

[Description]:

Trenimon is a compound with anti-cancer effects. Trenimon shows mutagenic actions in many species by inducing point and chromosomal mutations, sister-chromatid exchanges, recombination phenomena and phage induction. Trenimon can be used for the research of cancer[1][2][3][4].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Cell Cycle/DNA Damage >> DNA/RNA Synthesis

[In Vitro]

Trenimon (0.17 mM) penetrates readily into mouse lymphoma cells in vitro[1]. Trenimon (0.17 nM; 5 min-16 h) time-denpendently reduces the priming activity of DNA[2]. Trenimon (1 nM-10 μM; 10-20 min) leds HeLa cells death after 2 weeks with a dose of 10 μM and dose-dependently suppresses mitosis in cells[3].

[In Vivo]

Trenimon (0.25 mg/kg; i.p. once) rapidly depresseas of the cellular elements of the peripheral blood (granulocytes, lymphocytes, reticulocytes, platelets and erythrocytes), and reduces the cell number of bone marrow[4]. Trenimon (0.03 mg/kg; i.v. once per week for 52 weeks) shows an cancerogenic effect in vivo[4]. Animal Model: BR 46 male rats[4] Dosage: 0.03 mg/kg Administration: Intravenous injection; 0.03 mg/kg once per week for 52 weeks Result: Showed an cancerogenic effect and 24% animals developed malign tumors, and showed a induction time of the tumors is 16 months.

Chemical & Physical Properties

[ Density]:
1.727g/cm3

[ Boiling Point ]:
376.5ºC at 760 mmHg

[ Melting Point ]:
162.5-163ºC

[ Molecular Formula ]:
C₁₂H₁₃N₃O₂

[ Molecular Weight ]:
231.25100

[ Flash Point ]:
175.1ºC

[ Exact Mass ]:
231.10100

[ PSA ]:
43.17000

[ Index of Refraction ]:
1.846

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DK7175000

CHEMICAL NAME :: p-Benzoquinone, 2,3,5-tris(1-aziridinyl)-

CAS REGISTRY NUMBER :: 68-76-8

BEILSTEIN REFERENCE NO. :: 0238057

LAST UPDATED :: 199710

DATA ITEMS CITED :: 98

MOLECULAR FORMULA :: C12-H13-N3-O2

MOLECULAR WEIGHT :: 231.28

WISWESSER LINE NOTATION :: L6V DVJ B- AT3NTJ& C- AT3NTJ& E- AT3NTJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 500 ug/kg

TOXIC EFFECTS :: Blood - leukopenia

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 500 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 :: Parenteral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 500 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1560 ug/kg/1Y-I

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Lungs, Thorax, or Respiration - tumors Blood - tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 125 ug/kg

SEX/DURATION :: female 1 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - other measures of fertility

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 1 mg/kg

SEX/DURATION :: female 1 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - oogenesis

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 125 ug/kg

SEX/DURATION :: male 1 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Effects on Newborn - germ cell effects (in offspring)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 20 ug/kg

SEX/DURATION :: female 15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - cytological changes (including somatic cell genetic material)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 125 ug/kg

SEX/DURATION :: male 1 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Effects on Embryo or Fetus - fetal death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 125 ug/kg

SEX/DURATION :: male 1 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Effects on Newborn - weaning or lactation index (e.g., # alive at weaning per # alive at day 4)

TYPE OF TEST :: Specific locus test

TYPE OF TEST :: Cytogenetic analysis

TYPE OF TEST :: Sex chromosome loss and nondisjunction

TYPE OF TEST :: Sex chromosome loss and nondisjunction

TYPE OF TEST :: Dominant lethal test

TYPE OF TEST :: Heritable translocation test

TYPE OF TEST :: Dominant lethal test

TYPE OF TEST :: Micronucleus test

TYPE OF TEST :: Cytogenetic analysis

TYPE OF TEST :: Micronucleus test

TYPE OF TEST :: DNA inhibition

TYPE OF TEST :: DNA inhibition

TYPE OF TEST :: Cytogenetic analysis

TYPE OF TEST :: Cytogenetic analysis

TYPE OF TEST :: Sister chromatid exchange

TYPE OF TEST :: Sister chromatid exchange

TYPE OF TEST :: Dominant lethal test

TYPE OF TEST :: Dominant lethal test

TYPE OF TEST :: Sperm Morphology

TYPE OF TEST :: Heritable translocation test

TYPE OF TEST :: Micronucleus test

TYPE OF TEST :: Micronucleus test

TYPE OF TEST :: Cytogenetic analysis

TYPE OF TEST :: Cytogenetic analysis

TYPE OF TEST :: Sister chromatid exchange

TYPE OF TEST :: Sister chromatid exchange

TYPE OF TEST :: Micronucleus test

TYPE OF TEST :: Micronucleus test

TYPE OF TEST :: Micronucleus test

MUTATION DATA

TYPE OF TEST :: DNA damage

TEST SYSTEM :: Mammal - species unspecified Lymphocyte

DOSE/DURATION :: 14 mmol/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 65,21,1979 *** REVIEWS *** IARC Cancer Review:Animal Limited 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: 9,67,1975 IARC Cancer Review:Human Inadequate 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: 9,67,1975 IARC Cancer Review:Group 3 IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,367,1987 TOXICOLOGY REVIEW ATXKA8 Archiv fuer Toxikologie. (Berlin, Fed. Rep. Ger.) V.15-31, 1954-74. For publisher information, see ARTODN. Volume(issue)/page/year: 28,135,1971

Safety Information

[ RIDADR ]:
UN 3249

[ Packaging Group ]:
II

[ Hazard Class ]:
6.1(a)

Synthetic Route

Click to get detail synthetic route

Related Compounds

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