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Cas Database |
| Name |
Dimebolin |
EINECS | 638-815-4 |
| CAS No. | 3613-73-8 | Density | 1.13 g/cm3 |
| PSA | 21.06000 | LogP | 3.82160 |
| Solubility | N/A | Melting Point |
115-116 °C |
| Formula | C21H25N3 | Boiling Point | 505.7 °C at 760 mmHg |
| Molecular Weight | 319.45 | Flash Point | 259.7 °C |
| Transport Information | N/A | Appearance | White powder |
| Safety | Risk Codes | N/A | |
| Molecular Structure |
|
Hazard Symbols | N/A |
| 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; |
Article Data | 14 |
Dimebolin Synthetic route
- 140-76-1
2-methyl-5-vinylpyridine
- 19686-05-6
2.8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole
- 3613-73-8
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℃; |
- 1227258-81-2
tert-butyl 8-methyl-5-(2-(6-methylpyridin-3-yl)ethyl)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate
- 3613-73-8
dimebon
| Conditions | Yield |
|---|---|
| With lithium aluminium tetrahydride In tetrahydrofuran for 2h; Reflux; | 70% |
- 1445-73-4
1-Methyl-4-piperidone
- 21241-08-7
2-methyl-5-{2-[1-(4-methylphenyl)hydrazinyl]ethyl}pyridine
- 3613-73-8
dimebon
| Conditions | Yield |
|---|---|
| With acetic acid In water at 20℃; for 4h; Inert atmosphere; Reflux; | |
| With hydrogenchloride In isopropyl alcohol for 0.25h; |
- 1229621-60-6
N'-(1-methyl-piperidin-4-ylidene)-N-[2-(6-methyl-pyridin-3-yl)-ethyl]-N-p-tolyl-hydrazine
- 3613-73-8
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; |
- 3613-73-8
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 |
- 100189-17-1
2-(6-methylpyridin-3-yl) ethan-1-ol
- 3613-73-8
dimebon
| Conditions | Yield |
|---|---|
| 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 |
- 3613-73-8
dimebon
| Conditions | Yield |
|---|---|
| With sodium tetrahydroborate In methanol; water Inert atmosphere; | 0.046 g |
- 1296770-62-1
3-(2-azido-5-methylphenyl)pyridine
- 3613-73-8
dimebon
| Conditions | Yield |
|---|---|
| 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 |
- 1296770-72-3
1-methyl-3-(2-azido-5-methylphenyl)pyridinium triflate
- 3613-73-8
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 |
Dimebolin Specification
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 |
|---|---|---|---|---|---|
| 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. |
5. Use of Dimebolin
Dimebolin has been shown to inhibit brain cell death in preclinical studies of Alzheimer's disease and Huntington's disease, making it a potential treatment for these and other neurodegenerative diseases. Also it may have cognition-enhancing effects in healthy individuals.
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