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Identification
Name Fencamfamine
Accession Number DB01463
Type small molecule
Groups illicit, approved, withdrawn
Description

Fencamfamine (Glucoenergan, Reactivan) is a stimulant which was developed in the 1960s as an appetite suppressant, but was later withdrawn for this application due to problems with dependence and abuse.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. Reactivan is still rarely used for treating depressive day-time fatigue, lack of concentration and lethargy, particularly in individuals who have chronic medical conditions, as its favourable safety profile makes it the most suitable drug in some cases. [Wikipedia]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • 2-Aethylamino-3-phenyl-nor-camphan
  • 2-Ethylamino-3-phenyl-norcamphane hydrochloride
  • 2-Ethylamino-3-phenylnorcamphane hydrochloride
  • Fencamfamin
  • Fencamfamin hydrochloride
  • Fencamfamina [dcit]
  • Fencamfamine [inn-french]
  • Fencamfamine hydrochloride
  • Fencamfaminum [inn-latin]
  • Fencanfamina [inn-spanish]
Brand names
  • Euvitol
  • Glucoenergan
  • Reactivan
Brand name mixtures Not Available
Categories
  • Central Nervous System Stimulants
  • Antipsychotic Agents
CAS number 1209-98-9
Weight Average: 215.3339
Monoisotopic: 215.167399677
Chemical Formula C15H21N
InChI Key InChIKey=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
Plain Text
IUPAC Name
N-ethyl-3-phenylbicyclo[2.2.1]heptan-2-amine
SMILES
CCNC1C2CCC(C2)C1C1=CC=CC=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Phenethylamines
  • Amphetamines
Substructures
  • Aliphatic and Aryl Amines
  • Benzene and Derivatives
  • Phenethylamines
  • Aromatic compounds
  • Bicycloheptanes
  • Amphetamines
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.
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.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Route of elimination Not Available
Half life Not Available
Clearance Not Available
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
Pharmacoeconomics
Manufacturers Not Available
Packagers Not Available
Dosage forms
Form Route Strength
Syrup Oral
Tablet Oral
Prices Not Available
Patents Not Available
Properties
State solid
Melting point Not Available
Experimental Properties
Property Value Source
logP 3.20 [SANGSTER (1994)] PhysProp
Predicted Properties
Property Value Source
water solubility 2.95e-03 g/l ALOGPS
logP 3.46 ALOGPS
logP 3.21 ChemAxon Molconvert
logS -4.86 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 1 ChemAxon Molconvert
hydrogen donor count 1 ChemAxon Molconvert
polar surface area 12.03 ChemAxon Molconvert
rotatable bond count 3 ChemAxon Molconvert
refractivity 67.64 ChemAxon Molconvert
polarizability 26.13 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference
  1. Link
  2. DeLucia R, Planeta CS: Fencamfamine. Gen Pharmacol. 1990;21(2):161-3. Pubmed
External Links
Resource Link
PubChem Compound 14584 Link_out
PubChem Substance 46508161 Link_out
ChemSpider 13922 Link_out
Therapeutic Targets Database DAP001007 Link_out
Drug Product Database 0 Link_out
Wikipedia http://en.wikipedia.org/wiki/Fencamfamine 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
Food Interactions Not Available
Targets

1. Sodium-dependent dopamine transporter

Pharmacological action: yes
Actions: inhibitor

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

Organism class: human
UniProt ID: Q01959 Link_out
Gene: SLC6A3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. 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
  2. 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
Comments
Drug created on July 31, 2007 07:09 / Updated on November 10, 2010 13:48

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.