Fencamfamin
Identification
- Name
- Fencamfamin
- Accession Number
- DB01463
- Description
Fencamfamin (Glucoenergan, Reactivan) is a stimulant which was developed in the 1960s as an appetite suppressant, but was later withdrawn for this application due to problems with dependence and abuse. It is around half the potency of dexamphetamine, and is prescribed at a dose of 10-60mg, although abusers of the drug tend to rapidly develop tolerance and escalate their dose. Fencamfamin is used for treating depressive day-time fatigue, lack of concentration and lethargy. It is especially useful in patients with chronic conditions due to its favourable safety profile.
- Type
- Small Molecule
- Groups
- Experimental, Illicit, Withdrawn
- Structure
Structure for Fencamfamin (DB01463)
- Weight
- Average: 215.3339
Monoisotopic: 215.167399677 - Chemical Formula
- C15H21N
- Synonyms
- Fencamfamin
- Fencamfamina
- Fencamfamine
- Fencamfaminum
- Fencanfamina
- Phencamphamine
- External IDs
- DEA No. 1760
Pharmacology
- Indication
For the the treatment of depressive fatigue in convalescence and other debilitated states as well as in the treatment of depressive day-time fatigue, lack of concentration and lethargy.
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
Fencamfamine increases drive and mental alertness and an elevation of mood and a general feeling of well-being. It is a central nervous system stimulant, which increases locomotor activity.
- Mechanism of action
Fencamfamine acts as an indirect dopamine agonist. It releases dopamine by a similar mechanism to amphetamines, but is 10x less potent than dexamphetamine at producing this effect. The drug seems to inhibit the dopamine transporter (DAT) that removes dopamine from the synapses. This inhibition of DAT blocks the reuptake of dopamine and norepinephrine into the presynaptic neuron, increasing the amount of dopamine in the synapse. It also stimulates the release of dopamine and norepinephrine into the synapse. Finally, it increases the magnitude of dopamine release after a stimulus, increasing the salience of stimulus. Also unlike amphetamines, fencamfamine does not inhibit the action of monoamine oxidase enzymes and so is somewhat safer. Some experiments also suggest a role for opioid receptors in the activity of fencamfamine, as low doses can cause paradoxical sedation, and some effects of the drug are blocked by naloxone.
Target Actions Organism ASodium-dependent dopamine transporter inhibitorHumans - Absorption
- Not Available
- Volume of distribution
- Not Available
- Protein binding
- Not Available
- Metabolism
- Not Available
- Route of elimination
- Not Available
- Half-life
- Not Available
- Clearance
- Not Available
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
Overdosage is characterised by nausea, agitation and restlessness, dryness of the mouth, dizziness and tremor. In gross overdosage the above symptoms may also be associated with dyspnoea, tachycardia, disorientation and convulsions.
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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 Unlock Additional DataAcetazolamide The risk or severity of adverse effects can be increased when Acetazolamide is combined with Fencamfamin. Acetophenazine The risk or severity of adverse effects can be increased when Acetophenazine is combined with Fencamfamin. Aclidinium Fencamfamin may increase the central nervous system depressant (CNS depressant) activities of Aclidinium. Agomelatine The risk or severity of adverse effects can be increased when Fencamfamin is combined with Agomelatine. Alfentanil The risk or severity of adverse effects can be increased when Alfentanil is combined with Fencamfamin. Alimemazine The risk or severity of adverse effects can be increased when Alimemazine is combined with Fencamfamin. Almotriptan The risk or severity of adverse effects can be increased when Almotriptan is combined with Fencamfamin. Alosetron The risk or severity of adverse effects can be increased when Alosetron is combined with Fencamfamin. Alprazolam The risk or severity of adverse effects can be increased when Alprazolam is combined with Fencamfamin. Alverine The risk or severity of adverse effects can be increased when Fencamfamin is combined with Alverine. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Not Available
Products
- Product Ingredients
Ingredient UNII CAS InChI Key Fencamfamine hydrochloride 0M1J60BWEX 2240-14-4 CVFSMSTXULJISA-UHFFFAOYSA-N - International/Other Brands
- Glucoenergan / Reactivan
Categories
- ATC Codes
- N06BA06 — Fencamfamin
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Prenol lipids
- Sub Class
- Monoterpenoids
- Direct Parent
- Bicyclic monoterpenoids
- Alternative Parents
- Aromatic monoterpenoids / Aralkylamines / Benzene and substituted derivatives / Dialkylamines / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- Amine / Aralkylamine / Aromatic homopolycyclic compound / Aromatic monoterpenoid / Benzenoid / Bicyclic monoterpenoid / Hydrocarbon derivative / Monocyclic benzene moiety / Organic nitrogen compound / Organonitrogen compound
- Molecular Framework
- Aromatic homopolycyclic compounds
- External Descriptors
- Not Available
Chemical Identifiers
- UNII
- NME1I5IGBK
- CAS number
- 1209-98-9
- InChI Key
- IKFBPFGUINLYQI-UHFFFAOYSA-N
- InChI
- InChI=1S/C15H21N/c1-2-16-15-13-9-8-12(10-13)14(15)11-6-4-3-5-7-11/h3-7,12-16H,2,8-10H2,1H3
- IUPAC Name
- N-ethyl-3-phenylbicyclo[2.2.1]heptan-2-amine
- SMILES
- CCNC1C2CCC(C2)C1C1=CC=CC=C1
References
- General References
- DeLucia R, Planeta CS: Fencamfamine. Gen Pharmacol. 1990;21(2):161-3. [PubMed:1970543]
- Link [Link]
- External Links
- Human Metabolome Database
- HMDB0015508
- PubChem Compound
- 14584
- PubChem Substance
- 46508161
- ChemSpider
- 13922
- ChEBI
- 134895
- ChEMBL
- CHEMBL7010
- Therapeutic Targets Database
- DAP001007
- PharmGKB
- PA164747055
- Wikipedia
- Fencamfamine
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP 3.20 SANGSTER (1994) - Predicted Properties
Property Value Source Water Solubility 0.00295 mg/mL ALOGPS logP 3.46 ALOGPS logP 3.21 ChemAxon logS -4.9 ALOGPS pKa (Strongest Basic) 10.56 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 1 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 12.03 Å2 ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 67.64 m3·mol-1 ChemAxon Polarizability 26.13 Å3 ChemAxon Number of Rings 3 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 + 0.9756 Caco-2 permeable + 0.6244 P-glycoprotein substrate Non-substrate 0.648 P-glycoprotein inhibitor I Inhibitor 0.5239 P-glycoprotein inhibitor II Inhibitor 0.6499 Renal organic cation transporter Non-inhibitor 0.5876 CYP450 2C9 substrate Non-substrate 0.7441 CYP450 2D6 substrate Non-substrate 0.6052 CYP450 3A4 substrate Non-substrate 0.6348 CYP450 1A2 substrate Inhibitor 0.871 CYP450 2C9 inhibitor Non-inhibitor 0.6742 CYP450 2D6 inhibitor Inhibitor 0.7272 CYP450 2C19 inhibitor Inhibitor 0.645 CYP450 3A4 inhibitor Non-inhibitor 0.7812 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8237 Ames test Non AMES toxic 0.7967 Carcinogenicity Non-carcinogens 0.7716 Biodegradation Not ready biodegradable 0.6553 Rat acute toxicity 3.3827 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7712 hERG inhibition (predictor II) Inhibitor 0.5827
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- 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
- Seyfried CA: Dopamine uptake inhibiting versus dopamine releasing properties of fencamfamine: an in vitro study. Biochem Pharmacol. 1983 Aug 1;32(15):2329-31. [PubMed:6136281]
- Li SM, Campbell BL, Katz JL: Interactions of cocaine with dopamine uptake inhibitors or dopamine releasers in rats discriminating cocaine. J Pharmacol Exp Ther. 2006 Jun;317(3):1088-96. Epub 2006 Feb 14. [PubMed:16478825]
Drug created on July 31, 2007 07:09 / Updated on July 02, 2020 07:26
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