Phenmetrazine

Therapeutic Function Antiobesity drug Chemical Name 3-methyl-2-phenylmorpholine Common Name Oxazimedrine Structural Formula .  

Trade Name Manufacturer Country Year Introduced 

10 grams of -phenyl-a-methyl-/3,(3 -dihydroxy-diethylamine hydrochlgride (produced by hydrogenation in the presence of palladium and charcoal of -phenyl-a-methyl-(3-keto- -hydroxy-N-benzyl-diethylamine hydrochloride obtained from bromopropiophenone by reacting with benzyl-ethanolamine), are warmed with 10% hydrochloric acid for 6 hours on a water bath. 

After working up in the usual manner, the hydrochloride of the 2-phenyl-3-methyl-morpho-line crystallizes out from methanolic hydrochloric acid and acetone, MP= 182°C, according to U.S. Patent 2,835,669. 

Siemer, H. and Hengen, 0. U.S. Patent 3,018,222 January 23, 1962 assigned to Ravens-berg GmbH, Germany 

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Acylation of norephedrine (56) with the acid chloride from benzoylglycolic acid leads to the amide (57), Reduction with lithium aluminum hydride serves both to reduce the amide to the amine and to remove the protecting group by reduction (58), Cyclization by means of sulfuric acid (probably via the benzylic carbonium ion) affords phenmetrazine (59), In a related process, alkylation of ephedrine itself (60) with ethylene oxide gives the diol, 61, (The secondary nature of the amine in 60 eliminates the complication of dialkylation and thus the need to go through the amide.) Cyclization as above affords phendimetra-zine (62), - Both these agents show activity related to the parent acyclic molecule that is, the agents are CNS stimulants... 

Phenmetrazine 260 Phenobarbital 1, 268 Phenol phthal ei n 1, 316 Phenomorphan 294 Phenoperidine 302... 

Valethamate bromide dl-1 -Benzyl-4-(1,3-dicyano-1 -phenyl-propyl)piperidine HCI Dexetimide Benzylethanolamine Phenmetrazine... 

Cafllon (Ravensberg)-corab. with phenmetrazine-8-chlorotheophyllinate wfm... 

Cafilon (Yamanouchi)-comb. with phenmetrazine-8-chlorotheophyllinate... 

C9H13NO 104-63-2) see Indeloxacine Phenmetrazine 7-(2-benzylaminoethyl)theophylline (C15H19N5O2 22680-61-1) see Fenetylline Theodrenaline benzyl [(2R,35)-3-amino-2-hydroxy-4-phenylbutyl](2-methylpropyl)carbamate monohydrochloride (C22H3[C1N20j 160232-11-1) see Amprenavir 2-benzylamino-l-(4-methoxyphenyl)propane (C17H21NO 43229-65-8) see Fenoterol Formoterol benzyl [3-[(2-aminophenyl)carbamoyl]propyl]methyl> carbamate... 

Ci)H f 0 93-55-0) see Amfeprainone Dextropropoxyphene Eprazinone Mephenytoin Phendimetrazine Phenmetrazine Phenylpropanolamine Tamoxifen... 

Martin WR, Sloan JW, Sapira JD, et al Physiologic, subjective, and behavioral effects of amphetamine, methamphetamine, ephedrine, phenmetrazine, and methylphenidate in man. Clin Pharmacol Ther 12 245-258, 1971 McCormick TC Jr, McNeil TW Acute psychosis and Ritalin abuse. Tex State J Med... 

Chemical Structures. Figure 1 shows the chemical structures for 14 phenylethylamine compounds. Nine of these compounds are used clinically as anorectics (ii-amphetamine, phentermine, diethylpropion, phenmetrazine, phendimetrazine, clotermine, chlorphentermine, benzphetamine, and fenfluramine). Four of these compounds are not approved for clinical use and are reported to have hallucinogenic properties (MDA, PMA, DOM, and DOET). The final compound ( /-ephedrine) is used clinically for bronchial muscle relaxation, cardiovascular, and mydriatic effects. Figure 2 shows the chemical structure for MDMA, the methyl analog of MDA. MDMA is not approved for clinical use and has been reported to produce both LSD-like and cocaine-like effects. 

Figure 3 presents the mean levels of self-infusion for the 14 phenylethyl-amines shown in figure 1. Of all the drugs tested, injection rates were... 

In a summary of the human abuse literature on anorectic phenylethylamines, Griffiths et al. (1979) found there was a good correlation between the results of self-administration studies in animals and information about the subjective effects and abuse in man. Specifically, amphetamine, diethyl-propion, and phenmetrazine have been associated with numerous clinical case reports involving abuse, and these three compounds as well as benz-phetamine and /-ephedrine have shown similar subjective effects in drug abuser populations (Griffiths et al. 1979). In addition, fenfluramine was associated with low incidence of abuse in humans and did not maintain self-injection responding in animals. Chlorphentermine was similarly associated with low incidence of abuse in man, but did not maintain selfinjection uniformly in animals (Griffiths et al. 1979). 

Phenmetrazine Clinically used for short-term appetite suppression in the longer term its supposed benefits for weight control are very doubtful recreational use is rare, with weaker CNS effects than amphetamine, but it is still addictive. 

Mephentermine Methamphet amine Phendimetraz ine Phenmetrazine Phentermine... 

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