Meptazinol
- Product Name
- Meptazinol
- CAS No.
- 54340-58-8
- Chemical Name
- Meptazinol
- Synonyms
- MeptaMizol;MEPTAZINOL;Meptazinol A;Meptazinol-13C-d3;Meptazinol USP/EP/BP;MEPTAZINOL 54340-58-8;3-(3-ethyl-1-Methylazepan-3-yl)phenol;3-(1-Methyl-3-ethylhexahydro-1H-azepine-3-yl)phenol;3-(3-ethylhexahydro-1-methyl-1h-azepin-3-yl)-phenol;Phenol, 3-(3-ethylhexahydro-1-methyl-1H-azepin-3-yl)-
- CBNumber
- CB8841562
- Molecular Formula
- C15H23NO
- Formula Weight
- 233.35
- MOL File
- 54340-58-8.mol
Meptazinol Property
- Melting point:
- 127-133°C
- Boiling point:
- 354.8±35.0 °C(Predicted)
- Density
- 0.997
- pka
- 9.95±0.10(Predicted)
N-Bromosuccinimide Price
- Product number
- API0008709
- Product name
- MEPTAZINOL
- Purity
- 95.00%
- Packaging
- 1MG
- Price
- $460
- Updated
- 2021/12/16
- Product number
- API0008709
- Product name
- MEPTAZINOL
- Purity
- 95.00%
- Packaging
- 5MG
- Price
- $518
- Updated
- 2021/12/16
- Product number
- API0008709
- Product name
- MEPTAZINOL
- Purity
- 95.00%
- Packaging
- 10MG
- Price
- $574
- Updated
- 2021/12/16
- Product number
- CM200523
- Product name
- 3-(3-ethyl-1-methylazepan-3-yl)phenol
- Purity
- 97%
- Packaging
- 5g
- Price
- $505
- Updated
- 2021/12/16
Meptazinol Chemical Properties,Usage,Production
Originator
Meptid,Wyeth,UK,1983
Uses
Analgesic.
Definition
ChEBI: 3-(3-ethyl-1-methyl-3-azepanyl)phenol is a member of azepanes.
Manufacturing Process
2-(m-Methoxyphenyl)butyronitrile in dry ether was added to a stirred suspension of sodium amide in liquid ammonia. The mixture was stirred for 30 minutes then ethyl-4-iodobutyrate (99.25 g, 0.4 mol) in dry ether (200 ml) was added dropwise. The mixture was stirred at the temperature of refluxing liquid ammonia for 5 hours. Ammonium chloride (10 g) was added and the mixture allowed to warm to room temperature. Water (300 ml) was added, the organic layer separated, washed with water, 2 N sulfuric acid and water. After drying over magnesium sulfate and removing the ether, the product was distilled yielding ethyl 5-cyano-5-(mmethoxyphenyl)heptanoate.
That material was hydrogenated in cyclohexane using a Raney nickel catalyst. The product after distillation was recrystallized from ethyl acetate affording 10.0 g of 6-ethyl-(m-methoxyphenyl)hexahydro-2H-azepin-2one, MP 87°C to 88°C.
The azepinone (9.1 g) in dry tetrahydrofuran (50 ml) and ether (50 ml) was added dropwise to a stirred suspension of aluminum lithium hydride (7.5 g) in dry ether (50 ml). After heating under reflux for 3 hours the reaction mixture was worked up and distilled yielding 7.66 g of a compound which was a colorless oil, BP 108°C to 110°C/0.01 mm.
That product was then heated under reflux with 50% hydrobromic acid for 1.5
hours. The reaction mixture was evaporated to dryness and reevaporated with
three portions of propan-2-ol. The oil obtained was dissolved in propan-2-ol
and diluted with ether. 3-Ethyl-3-(m-hydroxyphenyl)hexahydro-1H-azepine
was obtained. That material in turn was reductively methylated by
hydrogenation in the presence of formaldehyde in absolute ethanol solution to
give 3-ethyl-3-(m-methoxyphenyl)-1-methylhexahydro-1H-azepine.
The methoxy group was converted to a hydroxy group by refluxing with 80%
HBr giving meptazinol hydrobromide.
Therapeutic Function
Analgesic
Clinical Use
Opioid analgesic used for moderate to severe pain
Drug interactions
Potentially hazardous interactions with other drugs
Antidepressants: possible CNS excitation or
depression with MAOIs - avoid; possible CNS
excitation or depression with moclobemide; possibly
increased sedative effects with tricyclics.
Antihistamines: increased sedative effects with
sedating antihistamines.
Antipsychotics: enhanced hypotensive and sedative
effects.
Dopaminergics: avoid with selegiline.
Nalmefene: avoid concomitant use.
Sodium oxybate: enhanced effect of sodium oxybate
- avoid
Metabolism
Meptazinol is extensively metabolised in the liver and is excreted mainly in the urine as the glucuronide conjugate. Less than 10% of a dose has been recovered from the faeces.
Meptazinol Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from Meptazinol manufacturers
- Product
- Meptazinol 54340-58-8
- Price
- US $0.00/gram
- Min. Order
- 1gram
- Purity
- 99%
- Supply Ability
- 10kg
- Release date
- 2022-02-17
- Product
- Meptazinol 54340-58-8
- Price
- US $1.10/g
- Min. Order
- 1g
- Purity
- 99.9%
- Supply Ability
- 100 Tons Min
- Release date
- 2021-06-16
- Product
- Meptazinol 54340-58-8
- Price
- US $2.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 100kg
- Release date
- 2018-12-25