Identification
- Generic Name
- Phenmetrazine
- DrugBank Accession Number
- DB00830
- Background
A sympathomimetic drug used primarily as an appetite depressant. Its actions and mechanisms are similar to dextroamphetamine.
- Type
- Small Molecule
- Groups
- Approved, Illicit
- Structure
Structure for Phenmetrazine (DB00830)
- Weight
- Average: 177.2429
Monoisotopic: 177.115364107 - Chemical Formula
- C11H15NO
- Synonyms
- 2-phenyl-3-methylmorpholine
- Fenmetrazin
- Fenmetrazina
- Phenmetrazin
- Phenmetrazine
- Phenmetrazinum
- External IDs
- PAL-592
- USAF Ge-1
Pharmacology
- Indication
Used as an anorectic in the treatment of obesity.
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
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.
- Mechanism of action
Phenmetrazine is thought to block the reuptake of norepinephrine and dopamine into the presynaptic neuron leading to an increase in the release of these monoamines into the extraneuronal space. Dopamine integrates incoming sensory stimuli, initiates and controls fine movement (nigro-neostriatal pathway), controls emotional behavior (midbrain mesolimbic-forebrain system) and controls hypothalamic-pituitary endocrine system (tubero-infundibular system). It is this latter effect on the tubero-infundibular systm that seems to lead to reduced food intake. Phenmetrazine also acts as a monoamine oxidase inhibitor.
Target Actions Organism ASodium-dependent noradrenaline transporter inhibitorHumans ASodium-dependent dopamine transporter inhibitorHumans - Absorption
Readily absorbed from the gastro-intestinal tract and buccal mucosa.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
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.
- Route of elimination
Not Available
- Half-life
16 to 31 hours
- Clearance
Not Available
- Adverse Effects
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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.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcebutolol Phenmetrazine may decrease the antihypertensive activities of Acebutolol. Aceclofenac The risk or severity of hypertension can be increased when Phenmetrazine is combined with Aceclofenac. Acemetacin The risk or severity of hypertension can be increased when Phenmetrazine is combined with Acemetacin. Acetylsalicylic acid The risk or severity of hypertension can be increased when Phenmetrazine is combined with Acetylsalicylic acid. Aclidinium The risk or severity of Tachycardia can be increased when Phenmetrazine is combined with Aclidinium. - Food Interactions
- Not Available
Products
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Ingredient UNII CAS InChI Key Phenmetrazine hydrochloride 6U85YRT588 1707-14-8 VJNXVAVKCZJOFQ-UHFFFAOYSA-N - International/Other Brands
- Preludin
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenylmorpholines. These are aromatic compounds containing a morpholine ring and a benzene ring linked to each other through a CC or a CN bond.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Oxazinanes
- Sub Class
- Morpholines
- Direct Parent
- Phenylmorpholines
- Alternative Parents
- Aralkylamines / Benzene and substituted derivatives / Oxacyclic compounds / Dialkylamines / Dialkyl ethers / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- Amine / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Dialkyl ether / Ether / Hydrocarbon derivative / Monocyclic benzene moiety / Organic nitrogen compound
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- morpholines (CHEBI:8067)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- XA501VL3VR
- CAS number
- 134-49-6
- InChI Key
- OOBHFESNSZDWIU-UHFFFAOYSA-N
- 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
- IUPAC Name
- 3-methyl-2-phenylmorpholine
- SMILES
- CC1NCCOC1C1=CC=CC=C1
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014968
- KEGG Compound
- C07432
- PubChem Compound
- 4762
- PubChem Substance
- 46504524
- ChemSpider
- 4598
- 8133
- ChEBI
- 8067
- ChEMBL
- CHEMBL1201208
- Therapeutic Targets Database
- DAP000860
- PharmGKB
- PA164747188
- Wikipedia
- Phenmetrazine
- MSDS
- Download (285 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Boehringer ingelheim pharmaceuticals inc
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 139 °C Not Available water solubility >5 mg/L Not Available logP 1.7 Not Available - Predicted Properties
Property Value Source Water Solubility 2.44 mg/mL ALOGPS logP 1.45 ALOGPS logP 1.79 Chemaxon logS -1.9 ALOGPS pKa (Strongest Basic) 8.22 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 21.26 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 52.47 m3·mol-1 Chemaxon Polarizability 20.1 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9723 Caco-2 permeable + 0.7082 P-glycoprotein substrate Substrate 0.5953 P-glycoprotein inhibitor I Non-inhibitor 0.7284 P-glycoprotein inhibitor II Non-inhibitor 0.9708 Renal organic cation transporter Inhibitor 0.5 CYP450 2C9 substrate Non-substrate 0.7859 CYP450 2D6 substrate Non-substrate 0.5985 CYP450 3A4 substrate Non-substrate 0.5798 CYP450 1A2 substrate Non-inhibitor 0.6065 CYP450 2C9 inhibitor Non-inhibitor 0.9188 CYP450 2D6 inhibitor Non-inhibitor 0.6846 CYP450 2C19 inhibitor Non-inhibitor 0.7002 CYP450 3A4 inhibitor Non-inhibitor 0.8524 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7188 Ames test Non AMES toxic 0.8037 Carcinogenicity Non-carcinogens 0.9102 Biodegradation Not ready biodegradable 0.9538 Rat acute toxicity 2.6487 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7603 hERG inhibition (predictor II) Non-inhibitor 0.7129
Spectra
- Mass Spec (NIST)
- Download (8.5 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 143.7633236 predictedDarkChem Lite v0.1.0 [M-H]- 136.42412 predictedDeepCCS 1.0 (2019) [M-H]- 143.7633236 predictedDarkChem Lite v0.1.0 [M-H]- 136.42412 predictedDeepCCS 1.0 (2019) [M+H]+ 144.6451236 predictedDarkChem Lite v0.1.0 [M+H]+ 139.89934 predictedDeepCCS 1.0 (2019) [M+H]+ 144.6451236 predictedDarkChem Lite v0.1.0 [M+H]+ 139.89934 predictedDeepCCS 1.0 (2019) [M+Na]+ 144.2170236 predictedDarkChem Lite v0.1.0 [M+Na]+ 149.3134 predictedDeepCCS 1.0 (2019) [M+Na]+ 144.2170236 predictedDarkChem Lite v0.1.0 [M+Na]+ 149.3134 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Norepinephrine:sodium symporter activity
- Specific Function
- Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
- Gene Name
- SLC6A2
- Uniprot ID
- P23975
- Uniprot Name
- Sodium-dependent noradrenaline transporter
- Molecular Weight
- 69331.42 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- Rothman RB, Katsnelson M, Vu N, Partilla JS, Dersch CM, Blough BE, Baumann MH: Interaction of the anorectic medication, phendimetrazine, and its metabolites with monoamine transporters in rat brain. Eur J Pharmacol. 2002 Jun 28;447(1):51-7. [Article]
- Rothman RB, Baumann MH: Therapeutic potential of monoamine transporter substrates. Curr Top Med Chem. 2006;6(17):1845-59. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Monoamine transmembrane transporter activity
- Specific Function
- Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
- Gene Name
- SLC6A3
- Uniprot ID
- Q01959
- Uniprot Name
- Sodium-dependent dopamine transporter
- Molecular Weight
- 68494.255 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- Rothman RB, Katsnelson M, Vu N, Partilla JS, Dersch CM, Blough BE, Baumann MH: Interaction of the anorectic medication, phendimetrazine, and its metabolites with monoamine transporters in rat brain. Eur J Pharmacol. 2002 Jun 28;447(1):51-7. [Article]
- Rothman RB, Baumann MH: Therapeutic potential of monoamine transporter substrates. Curr Top Med Chem. 2006;6(17):1845-59. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 02, 2024 22:45