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Identification
Name Phendimetrazine
Accession Number DB01579
Type small molecule
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.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
(+)-3,4-Dimethyl-2-phenylmorpholine
(+)-phendimetrazine
(2S,3S)-3,4-Dimethyl-2-phenylmorpholine
3-Phenyl-2-methylmorpholine
3,4-Dimethyl-2-phenylmorpholine
d-2-Phenyl-3,4-dimethylmorpholine
Salts Not Available
Brand names
Name Company
Adphen
Antapentan
Bacarate
Dyrexan
Hyrex
Mephenmetrazine
Prelu-2
Sedafamen
Wehless
X-trozine
Brand mixtures Not Available
Categories
  • Anorexigenic Agents
CAS number 634-03-7
Weight Average: 191.2695
Monoisotopic: 191.131014171
Chemical Formula C12H17NO
InChI Key InChIKey=MFOCDFTXLCYLKU-UHFFFAOYSA-N
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
Plain Text
IUPAC Name
3,4-dimethyl-2-phenylmorpholine
SMILES
CC1C(OCCN1C)C1=CC=CC=C1
Plain Text
Mass Spec show (8.7 KB)
Taxonomy
Kingdom Organic
Classes
  • Phenethylamines
  • Amphetamines
Substructures
  • Benzyl Alcohols and Derivatives
  • Ethers
  • Benzene and Derivatives
  • Aliphatic and Aryl Amines
  • Phenethylamines
  • Heterocyclic compounds
  • Aromatic compounds
  • Morpholines
  • Amphetamines
Pharmacology
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.
Pharmacodynamics 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.
Mechanism of action Phendimetrazine may act in a similar way to amphetamines in that it activates the alpha-adrenergic system to induce an appetite suppressive and metabolic increase effect. The drug also acts as a norepinephrine-dopamine releasing agent (NDRA). It can bind to and reverse the NET.
Absorption Peak plasma levels occur within 1 to 3 hours. Absorption is usually complete by 4 to 6 hours.
Volume of distribution Not Available
Protein binding Not Available
Metabolism 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
Route of elimination The major route of elimination is via the kidneys where most of the drug and metabolites are excreted.
Half life 19-24 hours
Clearance Not Available
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
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Valeant pharmaceuticals international
  • Numark laboratories inc
  • Dm graham laboratories inc
  • Sandoz inc
  • Shire richwood inc
  • Mm mast and co
  • Vitarine pharmaceuticals inc
  • Solvay pharmaceuticals
  • Teva pharmaceuticals usa inc
  • Ferndale laboratories inc
  • Abc holding corp
  • Camall co inc
  • Tg united labs llc
  • Private formulations inc
  • Forest pharmaceuticals inc
  • Actavis totowa llc
  • Barr laboratories inc
  • Inwood laboratories inc sub forest laboratories inc
  • Ivax pharmaceuticals inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Kv pharmaceutical co
  • Manufacturing chemists inc
  • Mikart inc
  • Nexgen pharma inc
  • Usl pharma inc
  • Watson laboratories inc
  • Wyeth ayerst laboratories
Packagers
Dosage forms
Form Route Strength
Tablet Oral
Prices
Unit description Cost Unit
Bontril Slow Release 105 mg 24 Hour Capsule 1.67 USD capsule
Bontril sr 105 mg capsule 1.1 USD capsule
Phendimetrazine Tartrate 105 mg 24 Hour Capsule 1.07 USD capsule
Bontril pdm 35 mg tablet 0.83 USD tablet
Bontril 105 mg capsule sa 0.48 USD capsule
Phendimetrazine Tartrate 35 mg tablet 0.24 USD tablet
Phendimetrazine 35 mg tablet 0.21 USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
boiling point 134.5 °C at 1.20E+01 mm Hg Not Available
Predicted Properties
Property Value Source
water solubility 2.43e+00 g/l ALOGPS
logP 2.01 ALOGPS
logP 2.17 ChemAxon
logS -1.9 ALOGPS
pKa (strongest basic) 7.28 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 2 ChemAxon
hydrogen donor count 0 ChemAxon
polar surface area 12.47 ChemAxon
rotatable bond count 1 ChemAxon
refractivity 57.76 ChemAxon
polarizability 21.99 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Compound C07904 Link_out
PubChem Compound 12460 Link_out
PubChem Substance 46506122 Link_out
ChemSpider 11950 Link_out
Therapeutic Targets Database DAP000574 Link_out
PharmGKB PA450902 Link_out
RxList http://www.rxlist.com/cgi/generic/phendime.htm Link_out
Drugs.com http://www.drugs.com/phendimetrazine.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Phendimetrazine Link_out
ATC Codes Not Available
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions
Drug Interaction
Chlorpromazine Decreased anorexic effect, may increases psychotic symptoms
Fluoxetine Risk of serotoninergic syndrome
Fluphenazine Decreased anorexic effect, may increase psychotic symptoms
Fluvoxamine Risk of serotoninergic syndrome
Guanethidine Phendimetrazine may decrease the effect of guanethidine.
Isocarboxazid Possible hypertensive crisis
Mesoridazine Decreased anorexic effect, may increase psychotic symptoms
Methotrimeprazine Decreased anorexic effect, may increase psychotic symptoms
Paroxetine Risk of serotoninergic syndrome
Perphenazine Decreased anorexic effect, may increase psychotic symptoms
Phenelzine Possible hypertensive crisis
Prochlorperazine Decreased anorexic effect, may increase pyschotic symptoms
Promethazine Decreased anorexic effect, may increase pyschotic symptoms
Propericiazine Decreased anorexic effect, may increase pyschotic symptoms
Rasagiline Possible hypertensive crisis
Thioridazine Decreased anorexic effect, may increase psychotic symptoms
Tramadol Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Trandolapril Phendimetrazine may reduce the efficacy of Trandolapril.
Tranylcypromine The MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of the amphetamine, Phendimetrazine. Concomitant therapy should be avoided.
Trifluoperazine Decreased anorexic effect, may increase psychotic symptoms
Triprolidine Triprolidine may reduce the sedative effect of the antihistamine, Phendimetrazine.
Food Interactions Not Available
Targets

1. Alpha-1A adrenergic receptor

Pharmacological action: yes
Actions: agonist

This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins

Organism class: human
UniProt ID: P35348 Link_out
Gene: ADRA1A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Bray GA: Drug Insight: appetite suppressants. Nat Clin Pract Gastroenterol Hepatol. 2005 Feb;2(2):89-95. Pubmed
  4. Bray GA: A concise review on the therapeutics of obesity. Nutrition. 2000 Oct;16(10):953-60. Pubmed
  5. Rothman RB, Baumann MH: Therapeutic potential of monoamine transporter substrates. Curr Top Med Chem. 2006;6(17):1845-59. Pubmed

2. Sodium-dependent noradrenaline transporter

Pharmacological action: yes
Actions: negative modulator

Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals

Organism class: human
UniProt ID: P23975 Link_out
Gene: SLC6A2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Rothman RB, Baumann MH: Therapeutic potential of monoamine transporter substrates. Curr Top Med Chem. 2006;6(17):1845-59. Pubmed

3. Alpha-1B adrenergic receptor

Pharmacological action: unknown
Actions: agonist

This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system

Organism class: human
UniProt ID: P35368 Link_out
Gene: ADRA1B Link_out
Protein Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Bray GA: Drug Insight: appetite suppressants. Nat Clin Pract Gastroenterol Hepatol. 2005 Feb;2(2):89-95. Pubmed
  4. Bray GA: A concise review on the therapeutics of obesity. Nutrition. 2000 Oct;16(10):953-60. Pubmed
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  6. Rothman RB, Baumann MH: Therapeutic potential of monoamine transporter substrates. Curr Top Med Chem. 2006;6(17):1845-59. Pubmed
Comments
Drug created on August 29, 2007 08:52 / Updated on February 08, 2013 16:20