Cypenamine (

INN Inns are generally establishments or buildings where travelers can seek lodging, and usually, food and drink. Inns are typically located in the country or along a highway; before the advent of motorized transportation they also provided accommo ...

, BAN), or cypenamine hydrochloride (

USAN 280px, "Samguk Sagi" Book 04. Silla's Records. In 512, Usan-guk（于山國）was Ulleungdo（鬱陵島） Usan-guk, or the State of Usan, occupied Ulleung-do and the adjacent islands during the Korean Three Kingdoms period. According to th ...

), also known as 2-phenylcyclopentylamine, is a psychostimulant drug which was developed by a group at the William S. Merrell Chemical Company in the 1940s. It is currently known only in

scientific research The scientific method is an empirical method for acquiring knowledge that has characterized the development of science since at least the 17th century (with notable practitioners in previous centuries; see the article history of scientific m ...

and has never been developed for

market Market is a term used to describe concepts such as: *Market (economics), system in which parties engage in transactions according to supply and demand *Market economy *Marketplace, a physical marketplace or public market Geography *Märket, an ...

use Use may refer to: * Use (law), an obligation on a person to whom property has been conveyed * Use (liturgy), a special form of Roman Catholic ritual adopted for use in a particular diocese * Use–mention distinction, the distinction between using ...

. Cypenamine is currently

legal Law is a set of rules that are created and are law enforcement, enforceable by social or governmental institutions to regulate behavior,Robertson, ''Crimes against humanity'', 90. with its precise definition a matter of longstanding debate. ...

throughout the entire

world In its most general sense, the term "world" refers to the totality of entities, to the whole of reality or to everything that is. The nature of the world has been conceptualized differently in different fields. Some conceptions see the worl ...

, and though its

chemical structure A chemical structure determination includes a chemist's specifying the molecular geometry and, when feasible and necessary, the electronic structure of the target molecule or other solid. Molecular geometry refers to the spatial arrangement of ...

has a vague similarity to certain controlled stimulants like

fencamfamine Fencamfamin ( INN), also known as fencamfamine or by the brand names Glucoenergan and Reactivan, is a stimulant which was developed by Merck in the 1960s. Medical uses Fencamfamin is still used, though rarely, for treating depressive day-time fa ...

, it is likely that it is too distant for it to be considered an illicit analogue under the

United States The United States of America (U.S.A. or USA), commonly known as the United States (U.S. or US) or America, is a country primarily located in North America. It consists of 50 states, a federal district, five major unincorporated territori ...

Federal Analogue Act The Federal Analogue Act, , is a section of the United States Controlled Substances Act passed in 1986 which allows any chemical "substantially similar" to a controlled substance listed in Schedule I or II to be treated as if it were listed in ...

of the Controlled Substances Act.

Chemistry

Stereochemistry

2-Phenylcyclopentan-1-amine is a compound with two

stereocenter In stereochemistry, a stereocenter of a molecule is an atom (center), axis or plane that is the focus of stereoisomerism; that is, when having at least three different groups bound to the stereocenter, interchanging any two different groups c ...

s. Thus, the following two enantiomeric pairs may exist: * (1''RS'',2''SR'')-''trans''-2-phenylcyclopentan-1-amine * (1''RS'',2''RS'')-''cis''-2-phenylcyclopentan-1-amine The

racemate In chemistry, a racemic mixture, or racemate (), is one that has equal amounts of left- and right-handed enantiomers of a chiral molecule or salt. Racemic mixtures are rare in nature, but many compounds are produced industrially as racemates. ...

(±)-''trans''-2-phenylcyclopentan-1-amine :1 mixture of (1''R'',2''S'')-''trans''-2-phenylcyclopentan-1-amine (box, left) and (1''S'',2''R'')-''trans''-2-phenylcyclopentan-1-amine (box, right)is the active ingredient of cypenamine. Furthermore, the

kinetic resolution In organic chemistry, kinetic resolution is a means of differentiating two enantiomers in a racemic mixture. In kinetic resolution, two enantiomers react with different reaction rates in a chemical reaction with a chiral catalyst or reagent, resul ...

of (±)-''trans''-2-phenylcyclopentan-1-amine by lipase B from ''Candida antarctica'' may be effectively performed by an aminolysis reaction. Racemic ''cis''-2-phenylcyclopentan-1-amine :1 mixture of (1''R'',2''R'')-''cis''-2-phenylcyclopentan-1-amine and (1''S'',2''S'')-''cis''-2-phenylcyclopentan-1-aminehas found no pharmacological application.

Homology

Cypenamine is a

homolog In biology, homology is similarity due to shared ancestry between a pair of structures or genes in different taxa. A common example of homologous structures is the forelimbs of vertebrates, where the wings of bats and birds, the arms of prima ...

tranylcypromine Tranylcypromine, sold under the brand name Parnate among others,Drugs.co Page accessed April 17, 2016 is a monoamine oxidase inhibitor (MAOI). More specifically, tranylcypromine acts as nonselective and irreversible inhibitor of the enzyme mono ...

, containing an expanded alicyclic ring that is two methylene units larger than the highly strained/reactive cyclopropane. The cyclohexane homologue has been reported, although the LD₅₀s were all less than for plain amphetamine, it was still a functional stimulant.

References

{{Monoamine releasing agents Amines Norepinephrine-dopamine releasing agents Sympathomimetics Stimulants

Chemistry

Stereochemistry

Homology

See also

References