Pseudophenmetrazine

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Pseudophenmetrazine
Pseudophenmetrazine.svg
Systematic (IUPAC) name
(±)-cis-3-methyl-2-phenylmorpholine
or
(±)-(2RS,3SR)-3-methyl-2-phenylmorpholine
Clinical data
Identifiers
13580-23-9
None
Chemical data
Formula C11H15NO
177.243 g/mol

Pseudophenmetrazine is a psychostimulant compound of the morpholine class. It is the N-demethylated and cis-configured analogue of phendimetrazine as well as the cis-configured stereoisomer of phenmetrazine.[1] In addition, along with phenmetrazine, it is believed to be one of the active metabolites of phendimetrazine, which itself is inactive and behaves merely as a prodrug.[2] Relative to phenmetrazine, pseudophenmetrazine is of fairly low potency, acting as a modest releasing agent of norepinephrine (EC50 = 514 nM), while its (+)-enantiomer is a weak releaser of dopamine (EC50 = 1,457 nM) whereas its (−)-enantiomer is a weak reuptake inhibitor of dopamine (Ki = 2,691 nM);[2][3] together as a racemic mixture with the two enantiomers combined, pseudophenmetrazine behaves overall more as a dopamine reuptake inhibitor (Ki = 2,630 nM),[2][3] possibly due to the (+)-enantiomer blocking the uptake of the (−)-enantiomer into dopaminergic neurons and thus preventing it from inducing dopamine release. Neither enantiomer has any significant effect on serotonin reuptake or release (both Ki = >10,000 nM and EC50 = >10,000 nM, respectively).[2][3]

See also[edit]

References[edit]

  1. ^ F.. Macdonald (1997). Dictionary of Pharmacological Agents. CRC Press. p. 1333. ISBN 978-0-412-46630-4. Retrieved 18 May 2012. 
  2. ^ a b c d Rothman RB, Katsnelson M, Vu N et al. (June 2002). "Interaction of the anorectic medication, phendimetrazine, and its metabolites with monoamine transporters in rat brain". European Journal of Pharmacology 447 (1): 51–7. doi:10.1016/S0014-2999(02)01830-7. PMID 12106802. 
  3. ^ a b c Partilla JS, Dempsey AG, Nagpal AS, Blough BE, Baumann MH, Rothman RB (October 2006). "Interaction of amphetamines and related compounds at the vesicular monoamine transporter". The Journal of Pharmacology and Experimental Therapeutics 319 (1): 237–46. doi:10.1124/jpet.106.103622. PMID 16835371.