134-49-6

Basic information

• Product Name: PHENMETRAZINE
• Synonyms: PHENMETRAZINE;3-methyl-2-phenylmorpholine;Oxazimedrine;2-Phenyl-3-methylmorpholine;A-66;Probese-P;Psychamine A 66;C07432
• CAS NO: 134-49-6
• Molecular Formula: C₁₁H₁₅NO
• Molecular Weight: 177.24
• EINECS: 205-143-4
• Mol File: 134-49-6.mol
• Article Data: 12

Chemical Properties

• Boiling Point: bp12 138-140°; bp1 104°
• Flash Point: 112.7 °C
• Appearance: /
• Density: 1.0290 (rough estimate)
• Refractive Index: 1.5302 (estimate)
• PKA: pKa 8.45 (Uncertain)
• CAS DataBase Reference: PHENMETRAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: PHENMETRAZINE(134-49-6)
• EPA Substance Registry System: PHENMETRAZINE(134-49-6)

Safety Data

• Hazardous Substances Data: 134-49-6(Hazardous Substances Data)

Usage

Originator

Preludin, Boehringer Ingelheim, US ,1956

Uses

Anorexic.

Definition

ChEBI: Phenmetrazine is a member of the class of morpholines that is morpholine substituted with a phenyl group at position 2 and a methyl group at position 3. It has a role as a metabolite and a sympathomimetic agent. It derives from a morpholine.

Manufacturing Process

10 grams of β-phenyl-α-methyl-β,β'-dihydroxy-diethylamine hydrochloride (produced by hydrogenation in the presence of palladium and charcoal of βphenyl-α-methyl-β-keto-β'-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-3methyl-morpholine crystallizes out from methanolic hydrochloric acid and acetone, MP = 182°C, according to US Patent 2,835,669.

Brand name

Preludin (Boehringer Ingelheim);Anorex;Bromadryl;Emagrin;Filon;Gratsidin;Marsin;Neo-zine;Prelazine.

Therapeutic Function

Antiobesity

World Health Organization (WHO)

Phenmetrazine, a sympathomimetic amine, was introduced in 1956 for use as an anorexic agent. Although preparations remain available, the use of phenmetrazine is no longer indicated for the treatment of obesity. Moreover, since it has been subject to abuse, and because dependence can occur, it is now controlled under Schedule II of the 1971 Convention on Psychotropic Substances. (Reference: (UNCPS2) United Nations Convention on Psychotropic Substances (II), , , 1971)

Pharmacology

Phenmetrazine is a sympathomimetic drug used primarily as an appetite depressant. Its actions and mechanisms are similar to dextroamphetamine. Amphetamines are non-catecholamine sympathomimetic amines with CNS stimulant activity. Phenmetrazine was originally sold under the tradename Preludin as an anorectic. It has since been removed from the market. 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.

InChI:InChI=1S/C11H15NO/c1-9-11(13-8-7-12-9)10-5-3-2-4-6-10/h2-6,9,11-12H,7-8H2,1H3

Upstream product

• 89100-80-1 4-formyl-3-methyl-2-phenylmorpholine 
• 634-03-7 trans-Phendimetrazine 
• 54804-28-3 (1RS,2SR)-2-(2-hydroxy-ethylamino)-1-phenyl-propan-1-ol 
• 91485-53-9 3-Isopropyl-2-methyl-4-(3-methyl-2-phenyl-morpholinomethyl)-1-phenyl-3-pyrazolin-5-on 
• 141-43-5 ethanolamine 
• 2114-00-3 2-bromo-1-phenyl-1-propanone 
• 19347-08-1 acetic acid 1-methyl-2-oxo-2-phenyl-ethyl ester 
• 6536-18-1 Morazone 
• 63991-20-8 2-(2-hydroxy-ethylamino)-1-phenyl-propan-1-ol; hydrochloride 
• 38234-04-7 3-methyl-2-phenyl-morpholin-4-ol 

Downstream Products

• 91485-53-9 3-Isopropyl-2-methyl-4-(3-methyl-2-phenyl-morpholinomethyl)-1-phenyl-3-pyrazolin-5-on 
• 91485-52-8 4-Isopropyl-2-methyl-3-(3-methyl-2-phenyl-morpholinomethyl)-1-phenyl-3-pyrazolin-5-on 
• 634-03-7 trans-Phendimetrazine 
• 95228-53-8 [2-(3,4-dimethoxy-phenyl)-1-methyl-ethyl]-(3t-methyl-2r-phenyl-morpholin-4-yl)-amine 
• 97297-07-9 (2-indol-3-yl-1-methyl-ethyl)-(3t-methyl-2r-phenyl-morpholin-4-yl)-amine 
• 97432-04-7 2-(3-methyl-2-phenyl-morpholin-4-ylamino)-1-phenyl-propan-1-ol 
• 98131-85-2 (3t-methyl-2r-phenyl-morpholin-4-yl)-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amine 
• 98763-25-8 (1-furan-2-yl-ethyl)-(3t-methyl-2r-phenyl-morpholin-4-yl)-amine 
• 95555-40-1 (1-methyl-2-phenoxy-ethyl)-(3t-methyl-2r-phenyl-morpholin-4-yl)-amine 
• 94998-95-5 (3t-methyl-2r-phenyl-morpholin-4-yl)-(1-methyl-3-phenyl-propyl)-amine 
• 94436-89-2 (3t-methyl-2r-phenyl-morpholin-4-yl)-(1-phenyl-ethyl)-amine 
• 95558-62-6 (3t-methyl-2r-phenyl-morpholin-4-yl)-phenethyl-amine 
• 94681-96-6 (2-cyclohexyl-3-methyl-morpholin-4-yl)-(1-methyl-2-phenyl-ethyl)-amine 

Related news

The individual and combined effects of PHENMETRAZINE (cas 134-49-6) and mgluR2/3 agonist LY379268 on the motivation to self-administer cocaine09/30/2019

The US Food and Drug Administration has not approved a treatment for cocaine addiction, possibly due in part to the fact that repeated cocaine use results in dysregulation of multiple neurotransmitter systems, including glutamate and dopamine, and an emergence of increased negative affective sta...detailed

PHENMETRAZINE (cas 134-49-6) or ephedrine? - Fooled by library search09/29/2019

Chemical and/or thermal conversion of analytes in a sample and/or GC injector can mislead the identification of analytes in a toxicological screening. In addition, library search can even more complicate the identification. The risk for false positive identification of phenmetrazine in an ephedr...detailed

Relevant articles and documents

Optical rotation and conformation. VI. N.M.R. spectra and conformation of some stereoisomeric 2.3-disubstituted morpholines and 5-oxomorpholines

-

Facile, efficient, and catalyst-free electrophilic aminoalkoxylation of olefins: Scope and application

A new one-pot electrophilic aminoalkoxylation reaction using olefin, cyclic ether, amine, and N-bromosuccinimide has been developed. The olefinic substrates and the cyclic ether partners can be flexibly varied to produce a range of amino ether derivatives. This novel protocol has been applied in the facile and efficient synthesis of biologically active morpholine compounds.

Photochemical decomposition of phenazone derivatives. Part 7: Mechanism of decomposition in aqueous solutions

-