Phenmetrazine

Phenmetrazine
Clinical data
Trade names	Preludin, others
Other names	Fenmetrazine; Oxazimedrine; Phenmetrazin; 3-Methyl-2-phenylmorpholine; 2-Phenyl-3-methylmorpholine; 3-Methyl-2-phenyltetrahydro-2H-1,4-oxazine; PAL-55; PAL55; Prellies
Routes of; administration	By mouth, Intravenous, Vaporized, Insufflated, Suppository
Drug class	Norepinephrine–dopamine releasing agent; Psychostimulant; Appetite suppressant
ATC code	None;
Legal status
Legal status	AU: S8 (Controlled drug); BR: Class A3 (Psychoactive drugs); CA: Schedule IV; DE: Anlage II (Authorized trade only, not prescriptible); UK: Class B; US: Schedule II; UN: Psychotropic Schedule II; SE: Förteckning II;
Pharmacokinetic data
Elimination half-life	8 hours
Excretion	Kidney
Identifiers
	IUPAC name 3-methyl-2-phenylmorpholine;
CAS Number	134-49-6 ;
PubChem CID	4762;
DrugBank	DB00830 ;
ChemSpider	4598 ;
UNII	XA501VL3VR;
KEGG	C07432 ;
ChEBI	CHEBI:8067;
ChEMBL	ChEMBL1201208 ;
CompTox Dashboard (EPA)	DTXSID5023455 ;
ECHA InfoCard	100.004.677
Chemical and physical data
Formula	C11H15NO
Molar mass	177.247 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1C(C2=CC=CC=C2)OCCN1;
	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 ; Key:OOBHFESNSZDWIU-UHFFFAOYSA-N ;
	(verify)

Phenmetrazine, sold under the brand name Preludin among others, is a stimulant drug first synthesized in 1952 and originally used as an appetite suppressant, but withdrawn from the market in the 1980s due to widespread misuse. It was initially replaced by its analogue phendimetrazine (under the brand name Prelu-2) which functions as a prodrug to phenmetrazine, but now it is rarely prescribed, due to concerns of misuse and addiction. Chemically, phenmetrazine is a substituted amphetamine containing a morpholine ring or a substituted phenylmorpholine.

^ Anvisa (31 March 2023). "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 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.

[1] Anvisa (31 March 2023). "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 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.

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