3-methyl-2-phenylmorpholine

• ChemBase ID: 709
• Molecular Formular: C11H15NO
• Molecular Mass: 177.2429
• Monoisotopic Mass: 177.11536411
• SMILES: O1C(C(NCC1)C)c1ccccc1
• Canonical SMILES: CC1NCCOC1c1ccccc1
• 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
• InChIKey: OOBHFESNSZDWIU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-methyl-2-phenylmorpholine
• IUPAC Traditional name: phenmetrazine
• Brand Name: Bromadryl; Cafilon; Marsin; Mefolin; Neo-zine; Phenmetrazin; Phenmetrazine hydrochloride; Preludin; Preludin hydrochloride; Probese-P; Probese-P hydrochloride; Psychamine A 66; Psychamine A 66 hydrochloride
• Synonyms: 2-Phenyl-3-Methylmorpholine; 3-Methyl-2-phenylmorpholine; Dexphenmetrazine; Fenmetrazina [INN-Spanish]; Phenmetraline hydrochloride; Phenmetrazinum [INN-Latin]; USAF Ge-1; Defenmetrazin; Fenmetrazin; Oxazimedrine; Phenmetrazine

Database IDs

• CAS Number: 134-49-6
• PubChem SID: 46504524; 160964172
• PubChem CID: 4762
• CHEMBL: 1201208
• Chemspider ID: 4598
• DrugBank ID: DB00830
• KEGG ID: C07432
• Unique Ingredient Identifier: XA501VL3VR
• Wikipedia Title: Phenmetrazine

CALCULATED PROPERTIES

ALOGPS 2.1

• LOG S: -1.86
• Solubility (Water): 2.44e+00 g/l
• Log P: 1.45

JChem

• Molar Refractivity: 52.4695 cm^3
• Polarizability: 21.035545 Å^3
• Polar Surface Area: 21.26 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.81888133
• LogD (pH = 7.4): 0.9080251
• Log P: 1.7894363

PROPERTIES

Physical Property

• Solubility: >5 mg/L
• Hydrophobicity(logP): 1.7

Pharmacology Properties

• Admin Routes: Oral, Intravenous, Vaporized, Insufflated, Suppository
• Excretion: Renal
• Half Life: 8 hours
• Legal Status: Class B (UK); Schedule II (US); Schedule IV (Canada)

DETAILS

DrugBank - DB00830

• Drug Groups: illicit; approved
• Description: A sympathomimetic drug used primarily as an appetite depressant. Its actions and mechanisms are similar to dextroamphetamine. [PubChem]
• Indication: Used as an anorectic in the treatment of obesity.
• 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.
• Toxicity: Adult monkeys have an LD₅₀ of 15 to 20 mg/kg, whereas for young monkeys the LD₅₀ is only 5 mg/kg. Symptoms of overdose include acute central nervous system stimulation, cardiotoxicity causing tachycardia, arrhythmias, hypertension, and cardiovascular collapse. Whilst some patients show signs of toxicity at blood concentrations of 20 µg/L, chronic abusers of amphetamine have been known to have blood concentration of up to 3000 µg/L.
• Affected Organisms: Humans and other mammals
• Biotransformation: Primarily hepatic (via CYP3A and CYP2D6). Resistant to metabolism by monoamine oxidase. Metabolism involves deamination to para-hydroxyamphetamine and phenylacetone; this latter compound is subsequently oxidize to benzoic acid and excreted as glucuronide or glycine (hippuric acid) conjugate. Smaller amounts of amphetamine are converted to norephedrine by oxidation.
• Absorption: Readily absorbed from the gastro-intestinal tract and buccal mucosa.
• Half Life: 16 to 31 hours
• External Links: Wikipedia