Introduction：Basic information about CAS 7761-45-7|Metoprine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Metoprine |
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| CAS Number | 7761-45-7 | Molecular Weight | 269.13000 |
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| Density | 1.447g/cm3 | Boiling Point | 483.7ºC at 760 mmHg |
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| Molecular Formula | C11H10Cl2N4 | Melting Point | 275-276ºC |
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| MSDS | / | Flash Point | 246.3ºC |
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Names
| Name | 5-(3,4-dichlorophenyl)-6-methylpyrimidine-2,4-diamine |
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| Synonym | More Synonyms |
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Metoprine BiologicalActivity
| 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]. |
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| Related Catalog | Research Areas >>CancerSignaling Pathways >>Epigenetics >>Histone MethyltransferaseSignaling Pathways >>Cell Cycle/DNA Damage >>AntifolateResearch Areas >>Neurological Disease |
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| 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. |
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| 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. |
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Chemical & Physical Properties
| Density | 1.447g/cm3 |
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| Boiling Point | 483.7ºC at 760 mmHg |
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| Melting Point | 275-276ºC |
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| Molecular Formula | C11H10Cl2N4 |
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| Molecular Weight | 269.13000 |
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| Flash Point | 246.3ºC |
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| Exact Mass | 268.02800 |
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| PSA | 77.82000 |
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| LogP | 4.08560 |
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| Index of Refraction | 1.678 |
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| InChIKey | VQJHOPSWBGJHQS-UHFFFAOYSA-N |
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| SMILES | Cc1nc(N)nc(N)c1-c1ccc(Cl)c(Cl)c1 |
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Toxicological Information
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 DATAACUTE 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
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Safety Information
Synonyms
| METOPRINE,METHODICHLOROPHEN |
| BW-197U |
| 2aov |
| DDMP |
| METOPRINE |
| SK 5265 |
| Methodichlorophen |
