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7761-45-7

7761-45-7 structure
7761-45-7 structure
  • Name: Metoprine
  • Chemical Name: 5-(3,4-dichlorophenyl)-6-methylpyrimidine-2,4-diamine
  • CAS Number: 7761-45-7
  • Molecular Formula: C11H10Cl2N4
  • Molecular Weight: 269.13000
  • Catalog: Signaling Pathways Cell Cycle/DNA Damage Antifolate
  • Create Date: 2018-02-26 08:00:00
  • Modify Date: 2025-08-21 19:27:26
  • Metoprine (BW 197U) is a potent histamine N-methyltransferase (HMT) inhibitor. Metoprine, a diaminopyrimidine derivative, can cross the blood-brain barrier and increase brain histamine levels by inhibiting HMT[1][2]. Metoprine is an antifolate and antitumor agent[3].
Name 5-(3,4-dichlorophenyl)-6-methylpyrimidine-2,4-diamine
Synonyms METOPRINE,METHODICHLOROPHEN
BW-197U
2aov
DDMP
METOPRINE
SK 5265
Methodichlorophen
Description Metoprine (BW 197U) is a potent histamine N-methyltransferase (HMT) inhibitor. Metoprine, a diaminopyrimidine derivative, can cross the blood-brain barrier and increase brain histamine levels by inhibiting HMT[1][2]. Metoprine is an antifolate and antitumor agent[3].
Related Catalog
In Vivo Metoprine (BW 197U; 2-10 mg/kg; IP) ameliorates the memory deficits induced by nucleus basalis magnocellularis (NBM) lesions in a dose-dependent manner[2]. Intraperitoneal administration of Metoprine produces various behavioral effects, including decreases in food intake and increases in water consumption[1]. Animal Model: Male Sprague-dawley rats (200-280g)[2] Dosage: 2, 5, 10 mg/kg Administration: IP Result: Ameliorated the memory deficits induced by nucleus basalis magnocellularis (NBM) lesions in a dose-dependent manner and significanty prolonged transfer latency at a high dose of 10 mg/kg.
References

[1]. Junichi Kitanaka, et al. Brain Histamine N-Methyltransferase As a Possible Target of Treatment for Methamphetamine Overdose. Drug Target Insights. 2016 Mar 2;10:1-7.

[2]. Zhong Chen, et al. Effects of brain histamine on memory deficit induced by nucleus basalis-lesion in rats. Acta Pharmacol Sin. 2002 Jan;23(1):66-70.

[3]. John R Horton, et al. Structural basis for inhibition of histamine N-methyltransferase by diverse drugs. J Mol Biol. 2005 Oct 21;353(2):334-344.
Density 1.447g/cm3
Boiling Point 483.7ºC at 760 mmHg
Melting Point 275-276ºC
Molecular Formula C11H10Cl2N4
Molecular Weight 269.13000
Flash Point 246.3ºC
Exact Mass 268.02800
PSA 77.82000
LogP 4.08560
Index of Refraction 1.678

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UV8180000
CHEMICAL NAME :
Pyrimidine, 2,4-diamino-5-(3,4-dichlorophenyl)-6-methyl-
CAS REGISTRY NUMBER :
7761-45-7
BEILSTEIN REFERENCE NO. :
0223622
LAST UPDATED :
199612
DATA ITEMS CITED :
7
MOLECULAR FORMULA :
C11-H10-Cl2-N4
MOLECULAR WEIGHT :
269.15
WISWESSER LINE NOTATION :
T6N CNJ BZ DZ ER CG DG& F1

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 :
7 mg/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 :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
50 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Tumorigenic - active as anti-cancer agent
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
40 mg/kg/21D-I
TOXIC EFFECTS :
Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
2500 ug/kg
SEX/DURATION :
female 7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
5 mg/kg
SEX/DURATION :
female 8-9 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
7500 ug/kg
SEX/DURATION :
female 6-8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)

MUTATION DATA

TEST SYSTEM :
Human
DOSE/DURATION :
2800 ug/kg
REFERENCE :
RBBIAL Revista Brasileira de Biologia. Brazilian Review of Biology. (Academia Brasileira de Ciencias, Caixa Postal 229, ZC-00 Rio de Janeiro, Brazil) V.1- 1941- Volume(issue)/page/year: 25,145,1965
Hazard Codes Xi
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