3,4-dimethyl-2-phenylmorpholine

• ChemBase ID: 1359
• Molecular Formular: C12H17NO
• Molecular Mass: 191.26948
• Monoisotopic Mass: 191.13101417
• SMILES: O1C(C(N(CC1)C)C)c1ccccc1
• Canonical SMILES: CC1N(C)CCOC1c1ccccc1
• InChI: InChI=1S/C12H17NO/c1-10-12(14-9-8-13(10)2)11-6-4-3-5-7-11/h3-7,10,12H,8-9H2,1-2H3
• InChIKey: MFOCDFTXLCYLKU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,4-dimethyl-2-phenylmorpholine
• IUPAC Traditional name: phendimetrazine
• Brand Name: Adphen; Antapentan; Bacarate; Bontril; Dyrexan; Hyrex; Mephenmetrazine; Sedafamen; Wehless; X-trozine; Prelu-2
• Synonyms: (+)-3,4-Dimethyl-2-phenylmorpholine; (+)-phendimetrazine; (2S,3S)-3,4-Dimethyl-2-phenylmorpholine; 3,4-Dimethyl-2-phenylmorpholine; 3-Phenyl-2-methylmorpholine; d-2-Phenyl-3,4-dimethylmorpholine; Phendimetrazine

Database IDs

• CAS Number: 634-03-7
• PubChem SID: 160964819; 46506122
• PubChem CID: 12460

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.39657155
• LogD (pH = 7.4): 1.9287926
• Log P: 2.1724842
• Molar Refractivity: 57.7642 cm^3
• Polarizability: 22.88145 Å^3
• Polar Surface Area: 12.47 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.01
• LOG S: -1.9
• Solubility (Water): 2.43e+00 g/l

DETAILS

DrugBank - DB01579

• Drug Groups: illicit; approved
• Description: Phendimetrazine is a weight loss medication. Phendimetrazine is chemically related to amphetamines and is a Schedule III drug under the Convention on Psychotropic Substances. In the United States, phendimetrazine is a Schedule III controlled substance under the Uniform Controlled Substances Act of 1970.
• Indication: Used in the management of exogenous obesity as a short term adjunct (a few weeks) in a regimen of weight reduction based on caloric restriction.
• Pharmacology: Phendimetrazine is a phenylalkylamine sympathomimetic amine with pharmacological activity similar to the prototype drugs of this class used in obesity, the amphetamines. Actions include central nervous system stimulation and elevation of blood pressure. Tachyphylaxis and tolerance has been demonstrated with all drugs of this class in which these phenomena have been looked for. Drugs of this class used in obesity are commonly known as ''anorectics or anorexigenics." It has not been established, however, that the action of such drugs in treating obesity is primarily one of appetite suppression. Other central nervous system actions or metabolic effects, may be involved.
• Toxicity: Acute overdosage of phendimetrazine may manifest itself by the following signs and symptoms: unusual restlessness, confusion, belligerance, hallucinations, and panic states. Fatigue and depression usually follow the central stimulation. Cardiovascular effects include arrhythmias, hypertension, or hypotension and circulatory collapse. Gastrointestinal symptoms include nausea, vomiting, diarrhea, and abdominal cramps. Poisoning may result in convulsions, coma and death.
• Affected Organisms: Humans and other mammals
• Biotransformation: Approximately 30% of a given dose of phendimetrazine is metabolized into phenmetrazine, which may account for part of its anorectic effect, and probably also influences abuse potential; individuals who metabolise a greater proportion of phendimetrazine into phenmetrazine are more likely to develop problems with dependence and addiction
• Absorption: Peak plasma levels occur within 1 to 3 hours. Absorption is usually complete by 4 to 6 hours.
• Half Life: 19-24 hours
• Elimination: The major route of elimination is via the kidneys where most of the drug and metabolites are excreted.
• External Links: Wikipedia; RxList; Drugs.com