Fencamfamine

Common Name

Fencamfamine Description

Fencamfamine (Glucoenergan, Reactivan) is a stimliant which was developed in the 1960s as an appetite suppressant, but was later withdrawn for this application due to problems with dependence and abuse.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, particliarly in individuals who have chronic medical conditions, as its favourable safety profile makes it the most suitable drug in some cases. [Wikipedia] Structure

Synonyms

Value Source 2-aethylamino-3-Phenyl-nor-camphanHMDB FencamfaminHMDB FencamfaminaHMDB 2-ethylamino-3-PhenylnorcamphaneMeSH N-Ethyl-3-phenylbicyclo(2.2.1)heptan-2-amineMeSH ReactivanMeSH Fencamfamine hydrochlorideMeSH

Chemical Formlia

C₁₅H₂₁N Average Molecliar Weight

215.3339 Monoisotopic Molecliar Weight

215.167399677 IUPAC Name

N-ethyl-3-phenylbicyclo[2.2.1]heptan-2-amine Traditional Name

fencamfamine CAS Registry Number

1209-98-9 SMILES

InChI Identifier

InChI Key

IKFBPFGUINLYQI-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Kingdom

Chemical entities Super Class

Organic compounds Class

Lipids and lipid-like moleclies Sub Class

Prenol lipids 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

Organonitrogen compound

Amine

Aromatic homopolycyclic compound

Molecliar Framework

Aromatic homopolycyclic compounds External Descriptors

Not Available Ontology Status

Expected but not Quantified Origin

Drug

Biofunction

Antipsychotic Agents

Central Nervous System Stimliants

Application

Pharmaceutical

Cellliar locations

Membrane

Physical Properties State

Solid Experimental Properties

Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility2.95e-03 g/LNot Available LogP3.20SANGSTER (1994)

Predicted Properties

Property Value Source Water Solubility0.0029 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 ŲChemAxon Rotatable Bond Count3ChemAxon Refractivity67.64 m³·mol^-1ChemAxon Polarizability26.13 ųChemAxon Number of Rings3ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

Spectra Spectra

Spectrum Type Description Splash Key Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

Biological Properties Cellliar Locations

Membrane

Biofluid Locations

Blood

Urine

Tissue Location

Not Available Pathways

Not Available Normal Concentrations

Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01463

21059682

details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01463

21059682

details

Abnormal Concentrations

Not Available Predicted Concentrations

Biofluid Value Original age Original sex Original condition Comments Blood0-5 uMAdlit (>18 years old)BothNormalPredicted based on drug qualities Blood0-2 umol/mmol creatinineAdlit (>18 years old)BothNormalPredicted based on drug qualities

Associated Disorders and Diseases Disease References

None Associated OMIM IDs

None External Links DrugBank ID

DB01463 DrugBank Metabolite ID

Not Available Phenol Explorer Compound ID

Not Available Phenol Explorer Metabolite ID

Not Available FoodDB ID

Not Available KNApSAcK ID

Not Available Chemspider ID

13922 KEGG Compound ID

Not Available BioCyc ID

Not Available BiGG ID

Not Available Wikipedia Link

Fencamfamine NuGOwiki Link

HMDB15508 Metagene Link

HMDB15508 METLIN ID

Not Available PubChem Compound

14584 PDB ID

Not Available ChEBI ID

101009

Product: Camostat (mesylate)

References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References

1. DeLucia R, Planeta CS: Fencamfamine. Gen Pharmacol. 1990;21(2):161-3. [PubMed:1970543 ]
2. South African Electronic Package Inserts [Link]

Enzymes

General function:

Involved in neurotransmitter:sodium symporter 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

Molecular weight:

68494.255

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 ]

PMID: 26951929

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Reverse transcriptase

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