54340-58-8 Usage
Originator
Meptid,Wyeth,UK,1983
Uses
Analgesic.
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 drugsAntidepressants: 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.
Check Digit Verification of cas no
The CAS Registry Mumber 54340-58-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,4,3,4 and 0 respectively; the second part has 2 digits, 5 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 54340-58:
(7*5)+(6*4)+(5*3)+(4*4)+(3*0)+(2*5)+(1*8)=108
108 % 10 = 8
So 54340-58-8 is a valid CAS Registry Number.
InChI:InChI=1/C15H23NO/c1-3-15(10-4-5-11-16(2)12-15)13-6-8-14(17)9-7-13/h6-9,17H,3-5,10-12H2,1-2H3
54340-58-8Relevant articles and documents
Preparation method of meptazinol impurity D hydrochloride
-
Paragraph 0048; 0049, (2019/05/08)
The invention provides a preparation method of meptazinol impurity D hydrochloride, successively comprising the following reaction steps: Step 1, using meptazinol hydrochloride as a raw material and washing with a first alkali solvent to obtain a free compound as shown in the formula I; Step 2, dissolving the compound as shown in the formula I in a first solvent, adding a second alkali solvent, adding Tf2O dropwise, and stirring for a period of time to obtain a compound as shown in the formula II; Step 3, carrying out a coupled reaction on the compound as shown in the formula I and the compound as shown in the formula II so as to obtain a compound as shown in the formula III; and Step 4, carrying out a reaction between the compound as shown in the formula III and a hydrochloric acid solution of methanol to obtain a compound meptazinol impurity D hydrochloride as shown in the formula V. The invention provides convenience for rapid preparation. Operation is simple; raw materials are cheap and easily available; post-treatment is simple; product purity is high; and yield is high.
PRODRUGS OF OPIOIDS AND USES THEREOF
-
Page/Page column 46-47, (2011/08/08)
The present invention concerns prodrugs of opioid analgesics and pharmaceutical compositions containing such prodrugs. Methods for providing more consistent pain relief by increasing the bioavailability of the opioid analgesic with the aforementioned prodrugs are provided. The invention also provides for decreasing the adverse GI side effects of opioid analgesics.
Combination of selected opioids with muscarine antagonists for treating urinary incontinence
-
, (2008/06/13)
Active compound combinations of compounds of group A, particularly opioids, and compounds of group B, particularly anti-muscarine agents and other substances suitable for treatment of an increased urge to urinate or urinary incontinence. Related pharmaceutical formulations and methods of treatment of an increased urge to urinate or urinary incontinence are also provided.
