3-PPP (''N''-''n''-propyl-3-(3-hydroxyphenyl)piperidine) is a mixed

sigma Sigma ( ; uppercase Σ, lowercase σ, lowercase in word-final position ς; ) is the eighteenth letter of the Greek alphabet. In the system of Greek numerals, it has a value of 200. In general mathematics, uppercase Σ is used as an operator ...

σ₁ and σ₂ receptor

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 ...

(with similar

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 ...

for both subtypes, though slightly higher affinity for the latter) and D₂ receptor

partial agonist In pharmacology, partial agonists are drugs that bind to and activate a given Receptor (biochemistry), receptor, but have only partial Intrinsic activity, efficacy at the receptor relative to a full agonist. They may also be considered Ligand (bio ...

which is used in

scientific research The scientific method is an empirical method for acquiring knowledge that has been referred to while doing science since at least the 17th century. Historically, it was developed through the centuries from the ancient and medieval world. The ...

. It shows

stereoselectivity In chemistry, stereoselectivity is the property of a chemical reaction in which a single reactant forms an unequal mixture of stereoisomers during a non- stereospecific creation of a new stereocenter or during a non-stereospecific transformation ...

in its

pharmacodynamics Pharmacodynamics (PD) is the study of the biochemistry, biochemical and physiology, physiologic effects of drugs (especially pharmaceutical drugs). The effects can include those manifested within animals (including humans), microorganisms, or comb ...

. (+)-3-PPP is the

enantiomer In chemistry, an enantiomer (Help:IPA/English, /ɪˈnænti.əmər, ɛ-, -oʊ-/ Help:Pronunciation respelling key, ''ih-NAN-tee-ə-mər''), also known as an optical isomer, antipode, or optical antipode, is one of a pair of molecular entities whi ...

that acts as an agonist of the sigma receptors; it is also an agonist of both D₂

presynaptic In the nervous system, a synapse is a structure that allows a neuron (or nerve cell) to pass an electrical or chemical signal to another neuron or a target effector cell. Synapses can be classified as either chemical or electrical, depending o ...

and postsynaptic receptors. Conversely, (−)-3-PPP, also known as preclamol (), acts as an agonist of presynaptic D₂ receptors but as an antagonist of postsynaptic D₂ receptors, and has

antipsychotic Antipsychotics, previously known as neuroleptics and major tranquilizers, are a class of Psychiatric medication, psychotropic medication primarily used to manage psychosis (including delusions, hallucinations, paranoia or disordered thought), p ...

effects. 3-PPP has also been reported to be a

monoamine reuptake inhibitor A monoamine reuptake inhibitor (MRI) is a drug that acts as a reuptake inhibitor of one or more of the three major monoamine neurotransmitters serotonin, norepinephrine, and dopamine by blocking the action of one or more of the respective monoamin ...

and possibly to act at

adrenergic receptor The adrenergic receptors or adrenoceptors are a class of G protein-coupled receptors that are targets of many catecholamines like norepinephrine (noradrenaline) and epinephrine (adrenaline) produced by the body, but also many medications like b ...

s or some other non-sigma receptor.

Synthesis

The Grignard reagent was prepared for 3-Bromoanisole 398-37-0(1) and this was reacted with 3-Bromopyridine 26-55-1(2) to give 3-(3-methoxyphenyl)pyridine 373-67-5(3). Reaction with 1-bromopropane 06-94-5occurred to give the quaternary salt PC13695099 (4a). Catalytic hydrogenation of the quat cation gave 3-(3-methoxyphenyl)-1-propylpiperidine 6562-23-4(5). Demethylation with hydrogen bromide then completed the synthesis of preclamol (6).

References

3-Hydroxyphenyl compounds 3-Phenylpiperidines Antipsychotics D2 antagonists Dopamine agonists Sigma agonists {{Nervous-system-drug-stub

Synthesis

See also

References