Identification

Name
Fencamfamine
Accession Number
DB01463
Type
Small Molecule
Groups
Experimental, Illicit, Withdrawn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(Glucoenergan, Reactivan) is a stimulant which was developed in the 1960s as an appetite suppressant, but was later withdrawn for this application due to problems with dependence and abuse.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
Synonyms
  • Fencamfamin
  • Fencamfamine
  • Fencamfaminum
  • Fencanfamina
Product Ingredients
IngredientUNIICASInChI Key
Fencamfamine hydrochloride0M1J60BWEX2240-14-4CVFSMSTXULJISA-UHFFFAOYSA-N
International/Other Brands
Glucoenergan / Reactivan
Categories
UNII
NME1I5IGBK
CAS number
1209-98-9
Weight
Average: 215.3339
Monoisotopic: 215.167399677
Chemical Formula
C15H21N
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

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.

TargetActionsOrganism
ASodium-dependent dopamine transporter
inhibitor
Human
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
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
DrugInteraction
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Fencamfamine is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when Fencamfamine is combined with 3,4-Methylenedioxyamphetamine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when Fencamfamine is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when Fencamfamine is combined with 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Fencamfamine is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when Fencamfamine is combined with 7-Nitroindazole.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when Fencamfamine is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.
AcepromazineThe risk or severity of adverse effects can be increased when Fencamfamine is combined with Acepromazine.
AceprometazineThe risk or severity of adverse effects can be increased when Fencamfamine is combined with Aceprometazine.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Fencamfamine.
Food Interactions
Not Available

References

General References
  1. DeLucia R, Planeta CS: Fencamfamine. Gen Pharmacol. 1990;21(2):161-3. [PubMed:1970543]
  2. 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
ATC Codes
N06BA06 — Fencamfamin

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP3.20SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.00295 mg/mLALOGPS
logP3.46ALOGPS
logP3.21ChemAxon
logS-4.9ALOGPS
pKa (Strongest Basic)10.56ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity67.64 m3·mol-1ChemAxon
Polarizability26.13 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9756
Caco-2 permeable+0.6244
P-glycoprotein substrateNon-substrate0.648
P-glycoprotein inhibitor IInhibitor0.5239
P-glycoprotein inhibitor IIInhibitor0.6499
Renal organic cation transporterNon-inhibitor0.5876
CYP450 2C9 substrateNon-substrate0.7441
CYP450 2D6 substrateNon-substrate0.6052
CYP450 3A4 substrateNon-substrate0.6348
CYP450 1A2 substrateInhibitor0.871
CYP450 2C9 inhibitorNon-inhibitor0.6742
CYP450 2D6 inhibitorInhibitor0.7272
CYP450 2C19 inhibitorInhibitor0.645
CYP450 3A4 inhibitorNon-inhibitor0.7812
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8237
Ames testNon AMES toxic0.7967
CarcinogenicityNon-carcinogens0.7716
BiodegradationNot ready biodegradable0.6553
Rat acute toxicity3.3827 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7712
hERG inhibition (predictor II)Inhibitor0.5827
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Bicyclic monoterpenoid / Aromatic monoterpenoid / Aralkylamine / Benzenoid / Monocyclic benzene moiety / Secondary amine / Secondary aliphatic amine / Organic nitrogen compound / Organopnictogen compound / Hydrocarbon derivative
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
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
  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:6136281]
  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:16478825]

Drug created on July 31, 2007 07:09 / Updated on November 02, 2018 08:42