Cypenamine
Encyclopedia
Cypenamine, or phenylcyclopentamine, is a stimulant
drug
. It is currently known only in scientific research
and has never been developed
for market
use
. The trans- isomer
is reported to be more active
than the racemate. Cypenamine is currently legal throughout the entire world
, and though its chemical structure
has a vague similarity to certain controlled
stimulants like fencamfamine
(Glucoenergan, Reactivan), it is likely that it is too distant for it to be considered an illicit
analogue under say the United States
(U.S.) Federal Analogue Act (FAA) of the Controlled Substances Act
(CSA).
s. Thus, the following four following stereoisomers may exist:
The racemate (±)-trans-2-phenylcyclopentan-1-amine [1:1 mixture of (1R,2S)-trans-2-phenylcyclopentan-1-amine (box, left) and (1S,2R)-trans-2-phenylcyclopentan-1-amine (box, right)] is the active ingredient of cypenamine. Furthermore, the kinetic resolution
of (±)-trans-2-phenylcyclopentan-1-amine by lipase B from Candida antarctica may effectivily performed by an aminolysis reaction.
Racemic cis-2-phenylcyclopentan-1-amine [1:1 mixture of (1R,2R)-cis-2-phenylcyclopentan-1-amine and (1S,2S)-cis-2-phenylcyclopentan-1-amine] has found no pharmacological application.
Stimulant
Stimulants are psychoactive drugs which induce temporary improvements in either mental or physical function or both. Examples of these kinds of effects may include enhanced alertness, wakefulness, and locomotion, among others...
drug
Drug
A drug, broadly speaking, is any substance that, when absorbed into the body of a living organism, alters normal bodily function. There is no single, precise definition, as there are different meanings in drug control law, government regulations, medicine, and colloquial usage.In pharmacology, a...
. It is currently known only in scientific research
Research
Research can be defined as the scientific search for knowledge, or as any systematic investigation, to establish novel facts, solve new or existing problems, prove new ideas, or develop new theories, usually using a scientific method...
and has never been developed
Drug development
Drug development is a blanket term used to define the process of bringing a new drug to the market once a lead compound has been identified through the process of drug discovery...
for market
Market
A market is one of many varieties of systems, institutions, procedures, social relations and infrastructures whereby parties engage in exchange. While parties may exchange goods and services by barter, most markets rely on sellers offering their goods or services in exchange for money from buyers...
use
Recreational drug use
Recreational drug use is the use of a drug, usually psychoactive, with the intention of creating or enhancing recreational experience. Such use is controversial, however, often being considered to be also drug abuse, and it is often illegal...
. The trans- isomer
Isomer
In chemistry, isomers are compounds with the same molecular formula but different structural formulas. Isomers do not necessarily share similar properties, unless they also have the same functional groups. There are many different classes of isomers, like stereoisomers, enantiomers, geometrical...
is reported to be more active
Activity (chemistry)
In chemical thermodynamics, activity is a measure of the “effective concentration” of a species in a mixture, meaning that the species' chemical potential depends on the activity of a real solution in the same way that it would depend on concentration for an ideal solution.By convention, activity...
than the racemate. Cypenamine is currently legal throughout the entire world
World
World is a common name for the whole of human civilization, specifically human experience, history, or the human condition in general, worldwide, i.e. anywhere on Earth....
, and though its chemical structure
Chemical structure
A chemical structure includes molecular geometry, electronic structure and crystal structure of molecules. Molecular geometry refers to the spatial arrangement of atoms in a molecule and the chemical bonds that hold the atoms together. Molecular geometry can range from the very simple, such as...
has a vague similarity to certain controlled
Controlled substance
A controlled substance is generally a drug or chemical whose manufacture, possession, or use are regulated by a government. This may include illegal drugs and prescription medications ....
stimulants like fencamfamine
Fencamfamine
Fencamfamine is a stimulant which was developed by Merck in the 1960s.-Medical uses:Fencamfamine is still used, though rarely, for treating depressive day-time fatigue, lack of concentration and lethargy, particularly in individuals who have chronic medical conditions, as its favourable safety...
(Glucoenergan, Reactivan), it is likely that it is too distant for it to be considered an illicit
Illicit
Illicit may refer to:* illicit antiquities* illicit drug trade** illicit drug use** Illicit Drug Anti-Proliferation Act* illicit major* illicit minor* illicit work* Illicit Streetwear clothing company* Illicit...
analogue under say the United States
United States
The United States of America is a federal constitutional republic comprising fifty states and a federal district...
(U.S.) Federal Analogue Act (FAA) of the Controlled Substances Act
Controlled Substances Act
The Controlled Substances Act was enacted into law by the Congress of the United States as Title II of the Comprehensive Drug Abuse Prevention and Control Act of 1970. The CSA is the federal U.S. drug policy under which the manufacture, importation, possession, use and distribution of certain...
(CSA).
Stereochemistry
2-Phenylcyclopentan-1-amine is a compound with two stereocenterStereocenter
A stereocenter or stereogenic center is an atom, bearing groups such that an interchanging of any two groups leads to a stereoisomer.A chirality center is a stereocenter consisting of an atom holding a set of ligands in a spatial arrangement which is not superposable on its mirror image...
s. Thus, the following four following stereoisomers may exist:
- (1R,2S)-trans-2-phenylcyclopentan-1-amine
- (1S,2R)-trans-2-phenylcyclopentan-1-amine
- (1R,2R)-cis-2-phenylcyclopentan-1-amine
- (1S,2S)-cis-2-phenylcyclopentan-1-amine
The racemate (±)-trans-2-phenylcyclopentan-1-amine [1:1 mixture of (1R,2S)-trans-2-phenylcyclopentan-1-amine (box, left) and (1S,2R)-trans-2-phenylcyclopentan-1-amine (box, right)] is the active ingredient of cypenamine. Furthermore, the kinetic resolution
Kinetic resolution
In kinetic resolution, two enantiomers show different reaction rates in a chemical reaction, thereby creating an excess of the less reactive enantiomer. This excess goes through a maximum and disappears on full completion of the reaction. Kinetic resolution is a very old concept in organic...
of (±)-trans-2-phenylcyclopentan-1-amine by lipase B from Candida antarctica may effectivily performed by an aminolysis reaction.
Racemic cis-2-phenylcyclopentan-1-amine [1:1 mixture of (1R,2R)-cis-2-phenylcyclopentan-1-amine and (1S,2S)-cis-2-phenylcyclopentan-1-amine] has found no pharmacological application.
Homology
Cypenamine is an obvious homologue, containing an expanded alicyclic ring that is two -CH2- units larger than the highly strained/reactive cyclopropane of tranylcypromine. Based on this logic, one would have to contend that the cyclobutane homologue is yet another possibility. The cyclohexane homologue is known to have been reported, although the LD50's were all less than for plain amphetamine, it was still a functional stimulant.See also
- AmphetamineAmphetamineAmphetamine or amfetamine is a psychostimulant drug of the phenethylamine class which produces increased wakefulness and focus in association with decreased fatigue and appetite.Brand names of medications that contain, or metabolize into, amphetamine include Adderall, Dexedrine, Dextrostat,...
- CyclopentamineCyclopentamineCyclopentamine is a sympathomimetic alkylamine, classified as a vasoconstrictor...
- FencamfamineFencamfamineFencamfamine is a stimulant which was developed by Merck in the 1960s.-Medical uses:Fencamfamine is still used, though rarely, for treating depressive day-time fatigue, lack of concentration and lethargy, particularly in individuals who have chronic medical conditions, as its favourable safety...
- MethamphetamineMethamphetamineMethamphetamine is a psychostimulant of the phenethylamine and amphetamine class of psychoactive drugs...
- PropylhexedrinePropylhexedrinePropylhexedrine is a stimulant drug related to methamphetamine. It is used mainly to provide temporary symptomatic relief of nasal congestion due to colds, allergies and allergic rhinitis...
- TranylcypromineTranylcypromineTranylcypromine is a drug of the substituted phenethylamine and amphetamine classes which acts as a monoamine oxidase inhibitor —it is a non-selective and irreversible inhibitor of the enzyme monoamine oxidase...