2C-B-morpholine, also known as 2C-B-norphenmetrazine or as 2-(4-bromo-2,5-dimethoxyphenyl)morpholine, is a
serotonin receptor modulator
5-HT receptors, 5-hydroxytryptamine receptors, or serotonin receptors, are a group of G protein-coupled receptor and ligand-gated ion channels found in multiple tissues including the central and peripheral nervous systems. They mediate both ex ...
of the
phenylmorpholine (
phenmetrazine
Phenmetrazine, sold under the brand name Preludin among others, is a stimulant drug first chemical synthesis, synthesized in 1952 and originally used as an appetite suppressant, but withdrawn drug, withdrawn from the market in the 1980s due to ...
) and
cyclized phenethylamine
Substituted phenethylamines (or simply phenethylamines) are a chemical class of organic compounds that are based upon the phenethylamine structure; the class is composed of all the derivative compounds of phenethylamine which can be formed by ...
groups.
It is a
ligand
In coordination chemistry, a ligand is an ion or molecule with a functional group that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's el ...
of the
serotonin
Serotonin (), also known as 5-hydroxytryptamine (5-HT), is a monoamine neurotransmitter with a wide range of functions in both the central nervous system (CNS) and also peripheral tissues. It is involved in mood, cognition, reward, learning, ...
5-HT2A receptor, with an
affinity
Affinity may refer to:
Commerce, finance and law
* Affinity (law), kinship by marriage
* Affinity analysis, a market research and business management technique
* Affinity Credit Union, a Saskatchewan-based credit union
* Affinity Equity Pa ...
of 20.6nM and an of 4%.
The drug showed 103-fold lower affinity for this receptor than
''R''(–)-DOB and had minimal
agonist
An agonist is a chemical that activates a Receptor (biochemistry), receptor to produce a biological response. Receptors are Cell (biology), cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an R ...
activity (with ''R''(–)-DOB having an of 51% in the assay), so for practical purposes would act as an antagonist at the 5-HT
2A receptor under most circumstances, despite being technically classified as a partial agonist.
2C-B-morpholine was first described in the
scientific literature
Scientific literature encompasses a vast body of academic papers that spans various disciplines within the natural and social sciences. It primarily consists of academic papers that present original empirical research and theoretical ...
by
Richard Glennon and colleagues by 2004.
See also
*
Substituted phenethylamine § Cyclized phenethylamines
*
Substituted phenylmorpholine
Substituted phenylmorpholines, or substituted phenmetrazines alternatively, are chemical derivatives of 2-phenylmorpholine or of the psychostimulant drug phenmetrazine.
Most such compounds act as Monoamine releasing agent, releasers of monoamine ...
*
2C-B-aminorex
2C-B-aminorex (2C-B-AR) is a recreational designer drug with psychedelic effects. It is a substituted aminorex derivative which was first identified in Sweden in June 2019. Structurally, it is a hybrid of 4-bromo-2,5-dimethoxyphenethylamine (2C ...
*
2C-B-BZP
4-Bromo-2,5-dimethoxy-1-benzylpiperazine (2C-B-BZP) is a psychoactive drug and research chemical of the piperazine chemical class which has been sold as a "designer drug". It produces stimulant effects similar to those of benzylpiperazine (BZP).
...
*
2C-B-PP
2,5-dimethoxy-4-bromophenylpiperazine (2C-B-PP) is a drug of the phenylpiperazine class. It acts as an agonist at serotonin receptor
5-HT receptors, 5-hydroxytryptamine receptors, or serotonin receptors, are a group of G protein-coupled rece ...
References
External links
2C-B-morpholine - Isomer Design
2C (psychedelics)
Bromoarenes
O-methylated phenols
Phenylethanolamines
Phenylmorpholines
Serotonin receptor modulators
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