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Lysergic acid piperidide (LA-Pip or LSD-Pip), also known as ''N''-piperidinyllysergamide, is a serotonin receptor modulator of the lysergamide family related to
lysergic acid diethylamide Lysergic acid diethylamide, commonly known as LSD (from German ; often referred to as acid or lucy), is a Semisynthesis, semisynthetic, Hallucinogen, hallucinogenic compound derived from ergot, known for its powerful psychological effects and ...
(LSD). It is the analogue of LSD in which the ''N'',''N''-di ethyl substitution has been replaced with an ''N''- piperidide
ring (The) Ring(s) may refer to: * Ring (jewellery), a round band, usually made of metal, worn as ornamental jewelry * To make a sound with a bell, and the sound made by a bell Arts, entertainment, and media Film and TV * ''The Ring'' (franchise), a ...
. The drug has fairly 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 ...
and
efficacy Efficacy is the ability to perform a task to a satisfactory or expected degree. The word comes from the same roots as '' effectiveness'', and it has often been used synonymously, although in pharmacology a distinction is now often made betwee ...
as a
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
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 ...
compared to LSD, though is variably less potent in terms of depending on the
assay An assay is an investigative (analytic) procedure in laboratory medicine, mining, pharmacology, environmental biology and molecular biology for qualitatively assessing or quantitatively measuring the presence, amount, or functional activity ...
. It also has high affinity for the serotonin 5-HT1A and 5-HT2C receptors. LA-Pip has about 8.5% of the antiserotonergic activity of LSD (relative to 2.0% for LSM-775 and 4.7% for LPD-824) in the isolated rat
uterus The uterus (from Latin ''uterus'', : uteri or uteruses) or womb () is the hollow organ, organ in the reproductive system of most female mammals, including humans, that accommodates the embryonic development, embryonic and prenatal development, f ...
''
in vitro ''In vitro'' (meaning ''in glass'', or ''in the glass'') Research, studies are performed with Cell (biology), cells or biological molecules outside their normal biological context. Colloquially called "test-tube experiments", these studies in ...
''. LA-Pip has been said to be non-
hallucinogen Hallucinogens, also known as psychedelics, entheogens, or historically as psychotomimetics, are a large and diverse class of psychoactive drugs that can produce altered states of consciousness characterized by major alterations in thought, mo ...
ic or much less psychedelic than LSD in humans. However, this does not appear to have actually been stated anywhere in the originally cited source. Other sources imply that LA-Pip has not been assessed in humans. Correspondingly, the dose range and potency of LA-Pip as a psychedelic relative to LSD have not been reported. LA-Pip 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 Albert Hofmann and colleagues by 1955. There were additional publications on the compound in the later 1950s. It has not been encountered as a
designer drug A designer drug is a structural or functional analog of a controlled substance that has been designed to mimic the pharmacological effects of the original drug, while avoiding classification as illegal and/or detection in standard drug tests. ...
as of 2020.


See also

*
Substituted lysergamide Lysergamides, also known as ergoamides or as lysergic acid amides, are amides of lysergic acid (LA). They are ergolines, with some lysergamides being found naturally in ergot as well as other fungi. Lysergamides are notable in containing embed ...
* Lysergic acid pyrrolidide (LPD-824) * Lysergic acid morpholide (LSM-775) * Lysergic acid 2-butyl amide (LSB) * Lysergic acid 2,4-dimethylazetidide (LA-SS-Az, LSZ) * 25B-NAcPip


References


External links


LA-Pip - Isomer Design
{{Ergolines 5-HT2A agonists Lysergamides 1-Piperidinyl compounds Serotonin receptor agonists