Movatterモバイル変換

[0]ホーム
URL:

Jump to content
WikipediaThe Free Encyclopedia
Search

Metapramine

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Metapramine
Clinical data
Trade namesProdastene, Timaxel
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Eliminationhalf-life7–8 hours
Identifiers
  • (rac)-10,11-dihydro-N,5-dimethyl-5H-dibenz[b,f]azepin-10-amine
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC16H18N2
Molar mass238.334 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • CNC1CC2=C(C=CC=C2)N(C)C3=CC=CC=C31

Metapramine (brand namesProdastene,Timaxel) is atricyclic antidepressant (TCA) developed byRhone Poulenc[1] that was introduced for the treatment ofdepression inFrance in 1984.[2][3] In addition to its efficacy againstaffective disorders, it also hasanalgesic properties,[4][5] and may be useful in the treatment ofpain.

Metapramine hasdesipramine-like effects, acting as anorepinephrine reuptake inhibitor without affecting thereuptake ofserotonin ordopamine.[6][7][8] It has also been shown to act as a low-affinityNMDA receptorantagonist.[9] Metapramine's direct effects onserotonin,histamine, andmuscarinic acetylcholine receptors have not been assayed, but uniquely among most TCAs, it has anecdotally been reported to lackanticholinergic effects.[8][10]

Synthesis

[edit]

A pair of syntheses has been reported in the patent literature:[11][1]

Thehydroboration betweeniminostilbene (1) andN,N-diethylaminoborane (2) gives 10-borohydro-5-methyl-10,11-dihydro-dibenzo[b,f]azepine (3). This is treated with methylchloramine (4), completing the synthesis of metapramine (5).

References

[edit]
  1. ^abUS 3622565, Fouche JC, Alexandre CG, "Dibenzazepine derivatives and their preparation", issued 23 November 1971, assigned to Rhone Poulenc SA 
  2. ^Dictionary of organic compounds. London: Chapman & Hall. 1996. p. 13.ISBN 0-412-54090-8.
  3. ^Vela JM, Buschmann H, Holenz J, Párraga A, Torrens A (2007)."Compounds launched in single countries".Antidepressants, Antipsychotics, Anxiolytics: From Chemistry and Pharmacology to Clinical Application. Weinheim: Wiley-VCH. p. 248.ISBN 978-3-527-31058-6.
  4. ^Michael-Titus A, Costentin J (December 1987). "Analgesic effects of metapramine and evidence against the involvement of endogenous enkephalins in the analgesia induced by tricyclic antidepressants".Pain.31 (3):391–400.doi:10.1016/0304-3959(87)90167-9.PMID 2827090.S2CID 39569622.
  5. ^Fialip J, Marty H, Aumaitre O, Bougerolle AM, Dordain G, Berger JA, Eschalier A (1992). "Antinociceptive activity of metapramine in mice. Relationship with its pharmacokinetic properties".Life Sciences.50 (3):161–168.doi:10.1016/0024-3205(92)90268-T.PMID 1731171.
  6. ^Dagonneau H, Fonlupt P, Pacheco H (1986). "[Effects, in rats, of metapramine and carpipramine on the uptake of catecholamines and serotonin; relationship with 3H-imipramine binding]".Comptes Rendus des Séances de la Société de Biologie et de Ses Filiales (in French).180 (1):43–48.PMID 3017518.
  7. ^Warter JM, Tranchant C, Marescaux C, Depaulis A, Lannes B, Vergnes M (1990). "Immediate effects of 14 non MAOI antidepressants in rats with spontaneous petit mal-like seizures".Progress in Neuro-Psychopharmacology & Biological Psychiatry.14 (2):261–270.doi:10.1016/0278-5846(90)90106-q.PMID 2106711.S2CID 8332732.
  8. ^abBonierbale M, Dufour H, Scotto JC, Sutter JM (1976). "[Metapramine: antidepressant and psycho-stimulant]".L'Encephale (in French).2 (3):219–223.PMID 1033059.
  9. ^Boireau A, Bordier F, Durand G, Doble A (1996). "The antidepressant metapramine is a low-affinity antagonist at N-methyl-D-aspartic acid receptors".Neuropharmacology.35 (12):1703–1707.doi:10.1016/S0028-3908(96)00122-0.PMID 9076749.S2CID 7244740.
  10. ^Dufour P, Billa JP, Fabre J, Roquebert J (1989). "[Evaluation of the central anticholinergic activity of antidepressants. Comparison of two experimental methods]".Annales Pharmaceutiques Françaises (in French).47 (3):135–141.PMID 2634929.
  11. ^Linares Hubert, GB1323219 (1973 to Rhone-poulenc S.a., Paris).
SSRIsTooltip Selective serotonin reuptake inhibitors
SNRIsTooltip Serotonin–norepinephrine reuptake inhibitors
NRIsTooltip Norepinephrine reuptake inhibitors
NDRIsTooltip Norepinephrine–dopamine reuptake inhibitors
NaSSAsTooltip Noradrenergic and specific serotonergic antidepressants
SARIsTooltip Serotonin antagonist and reuptake inhibitors
SMSTooltip Serotonin modulator and stimulators
Others
TCAsTooltip Tricyclic antidepressants
TeCAsTooltip Tetracyclic antidepressants
Others
Non-selective
MAOATooltip Monoamine oxidase A-selective
MAOBTooltip Monoamine oxidase B-selective
Miscellaneous
α1
Agonists
Antagonists
α2
Agonists
Antagonists
β
Agonists
Antagonists
AMPARTooltip α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor
KARTooltip Kainate receptor
NMDARTooltip N-Methyl-D-aspartate receptor
Group I
mGluR1Tooltip Metabotropic glutamate receptor 1
mGluR5Tooltip Metabotropic glutamate receptor 5
Group II
mGluR2Tooltip Metabotropic glutamate receptor 2
mGluR3Tooltip Metabotropic glutamate receptor 3
Group III
mGluR4Tooltip Metabotropic glutamate receptor 4
mGluR6Tooltip Metabotropic glutamate receptor 6
mGluR7Tooltip Metabotropic glutamate receptor 7
mGluR8Tooltip Metabotropic glutamate receptor 8
H1
Agonists
Antagonists
H2
Agonists
Antagonists
H3
Agonists
Antagonists
H4
Agonists
Antagonists
DATTooltip Dopamine transporter
(DRIsTooltip Dopamine reuptake inhibitors)
NETTooltip Norepinephrine transporter
(NRIsTooltip Norepinephrine reuptake inhibitors)
SERTTooltip Serotonin transporter
(SRIsTooltip Serotonin reuptake inhibitors)
VMATsTooltip Vesicular monoamine transporters
Others
5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT3–7
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
Classes
Antidepressants
(Tricyclic antidepressants(TCAs))
Antihistamines
Antipsychotics
Anticonvulsants
Anticholinergics
Others
Retrieved from "https://en.wikipedia.org/w/index.php?title=Metapramine&oldid=1307792041"
Categories:
Hidden categories:
[8]ページ先頭
©2009-2025 Movatter.jp