Phenmetrazine 2276394 221944477 2008-06-26T20:20:49Z Pithecanthropus 1029913 /* Abuse */ {{Drugbox| |IUPAC_name = ''3-methyl-2-phenylmorpholine'' | image=phenmetrazine.png | width=125 | PubChem=4762 | CAS_number=134-49-6 | DrugBank= | C=11 | H=15 | N=1 | O=1 | molecular_weight = 177.2456 | bioavailability= | metabolism = | elimination_half-life= 8 hours | excretion = [[Renal]] | pregnancy_category = | legal_AU = | legal_CA = Schedule IV | legal_UK = Class B | legal_US = Schedule II | legal_status = | routes_of_administration= Oral, [[Intravenous infusion|Intravenous]], [[Vaporize]]d, [[Insufflate]]d, [[Suppository]] }} '''Phenmetrazine''' is a [[stimulant]] of the central nervous system. It was previously sold under the trade name Preludin as an [[anorectic]]. Preludin has since been removed from the market. It was initially replaced by the weaker analogue [[Phendimetrazine]] (Bontril), but this is now only rarely prescribed, due to problems with abuse. Other names that have been used for Phenmetrazine include: Defenmetrazin, Fenmetrazin, Oxazimedrine, Phenmetraline. ==History== It was first patented in [[Germany]] in 1952 by [[Boehringer-Ingelheim]]. It was the result of a search by Thomae and Wick for an [[anorectic]] substance without the side-effects of [[amphetamine]].<ref name=martel>{{ cite journal | author=Martel, Antonio | title=Preludin (Phenmetrazine) in the Treatment of Obesity | journal=Can. Med. Assoc. J. | volume=76 | year=1957 | pages=117 }}</ref> Phenmetrazine was introduced into [[clinical]] use in 1954 in [[Europe]].<ref name=kalant>{{ cite book | author=Kalant, Oriana Josseau | title=The Amphetamines: Toxicity and Addiction | year=1966 }}</ref> ==Medical use== In clinical use phenmetrazine produces less nervousness, hyperexcitability, [[Euphoria (emotion)|euphoria]] and [[insomnia]] than the amphetamines.<ref name=jama>{{ cite journal | title=Phenmetrazine Hydrochloride | journal=J. Am. Med. Assoc. | volume=163 | issue=5 | pages=357 | year=1957 }}</ref> It tends not to increase [[heart rate]] as much as other stimulants.<ref name=martel /> Due to the relative lack of side-effects, one study found it well tolerated in children.<ref name=martel /> In a study of the effectiveness on weight loss between phenmetrazine and [[dextroamphetamine]], phenmetrazine was found to be slightly more efficient.<ref name=hampson>{{ cite journal | title=Phenmetrazine and Dexamphetamine in the Management of Obesity | author=Hampson, J | journal=The Lancet | volume=275 | issue=7137 | pages=1265 | year=1960 }}</ref> Even though the manufacturers claimed it had "exceptional safety and strikingly low incidence of side effects", within some years there were some reports of [[Amphetamine psychosis|psychotic]] reactions of the amphetamine type.<ref name=kalant /> ==Pharmacology== Phenmetrazine produces its action by causing release of [[noradrenaline]] and [[dopamine]] in the central nervous system.<ref>{{ cite journal | title=Interaction of the anorectic medication, phendimetrazine, and its metabolites with monoamine transporters in rat brain. | author=Rothman RB et al | journal=Eur J Pharmacol. | volume=447 | issue=1 | pages=51 | year=2002 }}[http://www.ncbi.nlm.nih.gov/sites/entrez?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=12106802 Abstract]</ref> After an oral dose, about 70% of the drug is excreted from the body within 24 hours. About 19% of that is excreted as the unmetabolised drug and the rest as various [[metabolite]]s.<ref name=clarkes>{{ cite book | title=Clarke's Analysis of Drugs and Poisons | author=Anthony C Moffat, M David Osselton and Brian Widdop | isbn=0-85369-473-7 }}</ref> In trials in rats it has been found that after [[subcutaneous]] administration, both the [[optical isomer]]s of phenmetrazine is equally effective in reducing food intake, but in [[oral]] administration the [[levo]] isomer is more effective. In terms of central stimulation however, the dextro isomer is about 4 times as effective in both methods of administration.<ref name=engelhardt>{{ cite journal | title=Studies of the Mechanism of the Anti-Appetite Action of Phenmetrazine | author=Engelhardt, A | journal=Biochem. Pharmacol. | volume=8 | issue=1 | pages=100 | year=1961 }}</ref> ==Abuse== It is by some considered to have a greater potential for [[addiction]] than the amphetamines, and has been abused in many countries, for example [[Sweden]]. When stimulant abuse first became prevalent in Sweden in the 1950s, phenmetrazine was preferred to [[amphetamine]] and [[methamphetamine]] by addicts, as it was considered the superior drug. In the autobiographical novel "Rush" by [[Kim Wozencraft]], intravenous phenmetrazine is described as the most euphoric and pro-sexual of the stimulants the author used. Phenmetrazine was classified as a narcotic in Sweden in 1959, and was taken completely off the market in 1965. At first the illegal demand was satisfied by smuggling from Germany and later Spain and Italy. At first Preludin tablets were smuggled, but soon the smugglers started bringing in raw phenmetrazine powder. Eventually Amphetamine became the dominant stimulant of abuse because of its easier availability. The drug was taken by [[The Beatles]] early in their career. [[Paul McCartney]] was one known user. McCartney's introduction to drugs started in [[Hamburg]], [[Germany]]. The Beatles had to play for hours, and they were often given "Prellies" (Preludin) by the maid that cleaned their housing arrangements, German customers, or by [[Astrid Kirchherr]] (whose mother bought them). McCartney would usually take one, but [[John Lennon]] would often take four or five.<ref name="Milesp66-67"> Miles 1998. pp66-67.</ref> As is often the case with stimulant drug abuse, the Beatles' use of Preludin has been described as stemming from the need to stay awake and continue working, rather than a simple desire to get high. ==References== <references/> {{Stimulants}} [[Category:Stimulants]] [[Category:Anorectics]] [[Category:Withdrawn drugs]] [[Category:Morpholines]] [[sv:Fenmetrazin]]