Phendimetrazine

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"Mephenmetrazine" redirects here. For other methyl substitutions of phenmetrazine, see Phenmetrazine § Substituted phenmetrazines.
Phendimetrazine
Clinical data
Trade namesBontril
AHFS/Drugs.comMonograph
Pregnancy
category
  • C (US)
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
Pharmacokinetic data
BioavailabilityPeak plasma levels occur within 1 to 3 hours. Absorption is usually complete by 4 to 6 hours
MetabolismHepatic
Elimination half-life19-24 hours
ExcretionUrinary elimination
Identifiers
  • 3,4-dimethyl-2-phenylmorpholine
JSmol)
  • O2C(c1ccccc1)C(N(C)CC2)C
  • InChI=1S/C12H17NO/c1-10-12(14-9-8-13(10)2)11-6-4-3-5-7-11/h3-7,10,12H,8-9H2,1-2H3 checkY
  • Key:MFOCDFTXLCYLKU-UHFFFAOYSA-N checkY
  (verify)

Phendimetrazine (Bontril, Adipost, Anorex-SR, Appecon, Melfiat, Obezine, Phendiet, Plegine, Prelu-2, Statobex) is a

appetite suppressant.[2]

Pharmacology

Phendimetrazine functions as a

releasing agent (NDRA).[3]

As an amphetamine congener, its structure incorporates the backbone of

pharmacokinetics over phenmetrazine as a therapeutic agent because its metabolization by demethylases
produces a more steady and prolonged exposure of active drug within the body. This decreases abuse potential as the peak blood-concentration of active phenmetrazine that's produced from a single dose of phendimetrazine is lower than a single therapeutically equivalent dose of phenmetrazine.

Indicated as a short-term secondary treatment for exogenous obesity, phendimetrazine immediate-release 35mg tablets are typically consumed one hour before meals, not to exceed three doses daily. Phendimetrazine is also manufactured as a 105mg extended-release capsule for once daily dosing, typically consumed 30 to 60 minutes before a morning meal. Whereas the immediate-release formulation has a maximum daily dosage of 210mg (6 tablets), the extended-release capsules have a maximum daily dosage of 105mg (one capsule).

Legality

According to the List of Psychotropic Substances under International Control published by the International Narcotics Control Board, phendimetrazine is a Schedule III controlled substance under the Convention on Psychotropic Substances.[4]

Synthesis

2-chloroethanol also works):[5]

Alkylation of ephedrine (1) with oxirane (2) gives the diol, N-(2-Hydroxyethyl) Pseudoephedrine [54275-43-3] [91688-17-4] (3). (The secondary nature of the amine in 1) eliminates the complication of dialkylation and thus the need to go through the amide.) Cyclization affords phendimetrazine (4).

Thieme Patents (Ex 2):[6][7][8]

The halogenation of Propiophenone [93-55-0] (1) with bromine gives 2-Bromopropiophenone [2114-00-3] (2). Further reaction with N-Methylethanolamine [109-83-1] (3) goes on to five CID:232614 [902267-47-4] (4). Cyclization with formic acid completed the synthesis of phendimetrazine (5).

Patent:[9]

The reaction between Ephedrine [299-42-3] (1) and ethyl chloroacetate [105-39-5] (2) in the presence of sodium hydride gives 4,5-dimethyl-6-phenylmorpholin-3-one, [5493-96-9] (3). The optional reduction of the lactam carbonyl with lithium aluminium hydride.

Additional method:[10]

See also

References

  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. PMID 18710555
    .
  3. PMID 17017961
    . Retrieved 2020-05-05.
  4. ^ "List of psychotropic substances under international control" (PDF). Archived from the original (PDF) on 2012-08-31. Retrieved 2005-06-15.
  5. ^ Otto, W. G. (7 March 1956). "Optisch aktives 2-Phenyl-3,4-dimethyl-morpholin". Angewandte Chemie. 68 (5): 181–182. doi:10.1002/ange.19560680508.
  6. ^ Werner Heel and Karl Zeile, U.S. patent 2,997,469 (1961 to Ingelheim, Germany, assignors to C. H. Boehringer Sohn, Ingelheim, Germany, a partnership).
  7. ^ , GB862198 (1961 to ILSE LIEBRECHT, JULIUS LIEBRECHT, WALTER MAYER LIST, WALTER MAYER-LIST).
  8. ^ , GB791416 (1958 to ILSE LIEBRECHT, JULIUS LIEBRECHT, WALTER MAYER LIST. WALTER MAYER-LIST).
  9. ^ Gannon Walter Francis & Poos George Ireland, U.S. patent 3,308,121 (1967 to Janssen Pharmaceuticals Inc).
  10. ^ https://eurekamag.com/research/031/845/031845550.php
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