Basic information
- CAS
2240-14-4- Standard SMILES
CCNC1C2CCC(C2)C1c1ccccc1.Cl- InChIKey
CVFSMSTXULJISA-UHFFFAOYSA-N- Molecular formula
- C15H22ClN
- Average molar mass
- 251.79 g/mol
- Monoisotopic mass
- 251.1440774
Overview
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(Glucoenergan, Reactivan) is a stimulant which was developed in the 1960s as an appetite suppressant, but was later withdrawn for this application due to problems with dependence and abuse.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]
Names & identifiers
- Preferred name
- Fencamfamine Hydrochloride
- IUPAC
- N-ethyl-3-phenylbicyclo[2.2.1]heptan-2-amine;hydrochloride
- English name
- Fencamfamine hydrochloride, drug standar D solution
- Molecular formula
- C15H21N.ClH
- Molecular weight
- 251.8
Names & synonyms
Fencamfamine hydrochlorideFencamfamin hydrochloride2240-14-4Fencamfamin HCl2-Ethylamino-3-phenyl-norcamphane hydrochloride2-Aethylamino-3-phenyl-nor-camphan0M1J60BWEXNSC-1722542-Ethylamino-3-phenylbicyclo(2.2.1)heptane hydrochlorideNSC1722542-Ethylamino-3-phenylbicyclo[2.2.1]heptane hydrochlorideRefChem:140111
Show more names
SicoclorfencamfaminehydrochlorideCVFSMSTXULJISA-XSGMKNMASA-NN-ethyl-3-phenyl-norbornan-2-aminen-ethyl-3-phenyl-2-norbornanaminhydrochloride2-ethylamino-3-phenyl-norcamphanehydrochloride2-aethylamino-3-phenyl-nor-camphanhydrochlorid
218-805-2GlucoenerganH 6103-Phenyl-N-ethyl-2-norbornanamine hydrochlorideBicyclo(2.2.1)heptan-2-amine, N-ethyl-3-phenyl-, hydrochlorideBicyclo[2.2.1]heptan-2-amine, N-ethyl-3-phenyl-, hydrochlorideAltimineEnvitrol
Database identifiers
Properties
Computed structural properties
- Topological polar surface area
- 12 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 3
- Heavy atoms
- 17
- Formal charge
- 0
- Complexity
- 232
Physicochemical properties
- Melting point
- 192 ° · 192°
- Flash point
- 11 °C · 11 °C
- storage temp.
- 2 · 2-8°C
- solubility
- DMSO (Slightly), Methanol (Slightly)
- form
- Solid
- color
- White to Light Beige
- Stability
- Hygroscopic
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 0 M1J60BWEX · 0M1J60BWEX
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 301 · H301+H311+H331
- Hazard Codes
- F,T
- Risk Statements
- 11 · 11-23/24/25-39/23/24/25
- Safety Statements
- 16 · 16-36/37-45
- Toxicity
- 50 in · LD50 in mice, rats (mg/kg): 135.0, 113.0 orally; 85.5, 68.5 s.c.; 15.7, 23.5 i.v. (Hotovy)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P261, P262, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P316, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 3 (100%)
Toxicology
Health Effects
Using large amounts of these drugs can result in a condition known as amphetamine psychosis -- which can result in auditory, visual and tactile hallucinations, intense paranoia, irrational thoughts and beliefs, delusions, and mental confusion.
Exposure RoutesOral
Toxicity Summary
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.
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
A loosely defined group of drugs that tend to increase behavioral alertness, agitation, or excitation. They work by a variety of mechanisms, but usually not by direct excitation of neurons. The many drugs that have such actions as side effects to their main therapeutic use are not included here.
Agents that control agitated psychotic behavior, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. They are used in SCHIZOPHRENIA; senile dementia; transient psychosis following surgery; or MYOCARDIAL INFARCTION; etc. These drugs are often referred to as neuroleptics alluding to the tendency to produce neurological side effects, but not all antipsychotics are likely to produce such effects. Many of these drugs may also be effective against nausea, emesis, and pruritus.
Uses & manufacturing
UsesFor 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.
Applications
UsesFencamfamine is a CNS stimulant. This is a controlled substance (stimulant).
Related reactions
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Compound notes
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