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CAS No.: | 3613-73-8 |
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Name: | Dimebolin |
Article Data: | 14 |
Cas Database | |
Molecular Structure: | |
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Formula: | C21H25N3 |
Molecular Weight: | 319.45 |
Synonyms: | 1H-Pyrido[4,3-b]indole,2,3,4,5-tetrahydro-2,8-dimethyl-5-[2-(6-methyl-3-pyridyl)ethyl]- (8CI);2,3,4,5-Tetrahydro-2,8-dimethyl-5-[2-(6-methylpyridin-3-yl)ethyl]-1H-pyrido[4,3-b]indole;Dimeboline;Dimebon;Dimebone;Latrepirdine;Preparation 84; |
EINECS: | 638-815-4 |
Density: | 1.13 g/cm3 |
Melting Point: | 115-116 °C |
Boiling Point: | 505.7 °C at 760 mmHg |
Flash Point: | 259.7 °C |
Appearance: | White powder |
PSA: | 21.06000 |
LogP: | 3.82160 |
2-methyl-5-vinylpyridine
2.8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole
dimebon
Conditions | Yield |
---|---|
With potassium phosphate In ISOPROPYLAMIDE at 100℃; for 24h; Inert atmosphere; | 80% |
With potassium hydroxide In 1-methyl-pyrrolidin-2-one at 100℃; | 55% |
With potassium hydroxide In diethylene glycol dimethyl ether at 120℃; for 42h; Product distribution / selectivity; | 52% |
With sodium ethanolate; sodium In dimethyl sulfoxide at 90 - 95℃; | |
With potassium phosphate In ISOPROPYLAMIDE at 130℃; |
tert-butyl 8-methyl-5-(2-(6-methylpyridin-3-yl)ethyl)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate
dimebon
Conditions | Yield |
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With lithium aluminium tetrahydride In tetrahydrofuran for 2h; Reflux; | 70% |
1-Methyl-4-piperidone
2-methyl-5-{2-[1-(4-methylphenyl)hydrazinyl]ethyl}pyridine
dimebon
Conditions | Yield |
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With acetic acid In water at 20℃; for 4h; Inert atmosphere; Reflux; | |
With hydrogenchloride In isopropyl alcohol for 0.25h; |
N'-(1-methyl-piperidin-4-ylidene)-N-[2-(6-methyl-pyridin-3-yl)-ethyl]-N-p-tolyl-hydrazine
dimebon
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol; water at 100℃; for 0.5h; | |
Stage #1: N'-(1-methyl-piperidin-4-ylidene)-N-[2-(6-methyl-pyridin-3-yl)-ethyl]-N-p-tolyl-hydrazine With hydrogenchloride; water In ethanol at 80℃; for 1.5h; Stage #2: With sodium hydroxide In ethanol; water pH=14; | |
Stage #1: N'-(1-methyl-piperidin-4-ylidene)-N-[2-(6-methyl-pyridin-3-yl)-ethyl]-N-p-tolyl-hydrazine With hydrogenchloride In ethanol at 80℃; for 1.5h; Reflux; Stage #2: With sodium hydroxide In ethanol; water pH=14; |
dimebon
Conditions | Yield |
---|---|
With sodium hydroxide In 2-methyltetrahydrofuran; water for 1.25h; |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 0 °C / Reflux; Inert atmosphere 1.2: 1 h / Inert atmosphere 2.1: phosphorus tribromide / diethyl ether / 3 h / 0 °C / Inert atmosphere 3.1: N,N-dimethyl-formamide / 15 h / 60 °C / Inert atmosphere 4.1: sodium tetrahydroborate / methanol; water / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: potassium phosphate / ISOPROPYLAMIDE / 22 h / 100 °C 2: hydrogenchloride / isopropyl alcohol / 0.25 h View Scheme |
2-(6-methylpyridin-3-yl) ethan-1-ol
dimebon
Conditions | Yield |
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Multi-step reaction with 3 steps 1: phosphorus tribromide / diethyl ether / 3 h / 0 °C / Inert atmosphere 2: N,N-dimethyl-formamide / 15 h / 60 °C / Inert atmosphere 3: sodium tetrahydroborate / methanol; water / Inert atmosphere View Scheme |
dimebon
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol; water Inert atmosphere; | 0.046 g |
3-(2-azido-5-methylphenyl)pyridine
dimebon
Conditions | Yield |
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Multi-step reaction with 5 steps 1: dichloromethane / 20 °C / Inert atmosphere 2: dirhodium(II) tetrakis(perfluorobutyrate) / toluene / 15 h / 90 °C / Inert atmosphere; Molecular sieve 3: potassium hydroxide / water / 2 h / 90 °C / Inert atmosphere 4: N,N-dimethyl-formamide / 15 h / 60 °C / Inert atmosphere 5: sodium tetrahydroborate / methanol; water / Inert atmosphere View Scheme | |
Multi-step reaction with 5 steps 1: dichloromethane / 20 °C / Inert atmosphere 2: ruthenium trichloride hydrate / Isopropyl acetate / 15 h / 80 °C / Inert atmosphere 3: potassium hydroxide / water / 2 h / 90 °C / Inert atmosphere 4: N,N-dimethyl-formamide / 15 h / 60 °C / Inert atmosphere 5: sodium tetrahydroborate / methanol; water / Inert atmosphere View Scheme |
1-methyl-3-(2-azido-5-methylphenyl)pyridinium triflate
dimebon
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: dirhodium(II) tetrakis(perfluorobutyrate) / toluene / 15 h / 90 °C / Inert atmosphere; Molecular sieve 2: potassium hydroxide / water / 2 h / 90 °C / Inert atmosphere 3: N,N-dimethyl-formamide / 15 h / 60 °C / Inert atmosphere 4: sodium tetrahydroborate / methanol; water / Inert atmosphere View Scheme | |
Multi-step reaction with 4 steps 1: ruthenium trichloride hydrate / Isopropyl acetate / 15 h / 80 °C / Inert atmosphere 2: potassium hydroxide / water / 2 h / 90 °C / Inert atmosphere 3: N,N-dimethyl-formamide / 15 h / 60 °C / Inert atmosphere 4: sodium tetrahydroborate / methanol; water / Inert atmosphere View Scheme |
1. Introduction of Dimebolin
Dimebolin, with the IUPAC Name of 2,8-dimethyl-5-[2-(6-methylpyridin-3-yl)ethyl]-3,4-dihydro-1H-pyrido[4,3-b]indole, is one kind of solid. And its Classification Code is Reproductive Effect. It is an antihistamine drug and is an orally-active small molecule compound.
2. Properties of Dimebolin
Dimebolin has the following property data: (1)XLogP3-AA: 3.5; (2)H-Bond Donor: 0; (3)H-Bond Acceptor: 2; (4)Surface Tension: 41.5 dyne/cm; (5)Density: 1.13 g/cm3; (6)Flash Point: 259.7 °C; (7)Enthalpy of Vaporization: 77.55 kJ/mol; (8)Boiling Point: 505.7 °C at 760 mmHg; (9)Vapour Pressure: 2.37E-10 mmHg at 25 °C.
3. Structure Descriptors of Dimebolin
You could convert the following datas into the molecular structure:
InChI: InChI=1S/C21H25N3/c1-15-4-7-20-18(12-15)19-14-23(3)10-9-21(19)24(20)11-8-17-6-5-16(2)22-13-17/h4-7,12-13H,8-11,14H2,1-3H3
InChIKey: InChIKey=JNODQFNWMXFMEV-UHFFFAOYSA-N
Smiles: n1(c2c(c3cc(ccc13)C)CN(CC2)C)CCc1cnc(cc1)C
4. Toxicity of Dimebolin
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
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mouse | LD50 | intraperitoneal | 178mg/kg (178mg/kg) | Russian Pharmacology and Toxicology Vol. 31, Pg. 105, 1968. | |
mouse | LDLo | oral | 356mg/kg (356mg/kg) | Farmakologiya i Toksikologiya Vol. 46(5), Pg. 90, 1983. |