DEIMDHPCA, also known as 3,5-seco-LSD, is an

indole Indole is an organic compound with the formula . Indole is classified as an aromatic heterocycle. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered pyrrole ring. Indoles are derivatives of indole ...

derivative In mathematics, the derivative is a fundamental tool that quantifies the sensitivity to change of a function's output with respect to its input. The derivative of a function of a single variable at a chosen input value, when it exists, is t ...

and a "partial" or simplified

ergoline Ergoline is a core structure in many alkaloids and their synthetic derivatives. Ergoline alkaloids were first characterized in ergot. Some of these are implicated in the condition of ergotism, which can take a convulsive form or a gangrenous for ...

which is closely related to the highly potent

serotonergic psychedelic Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary mental states (known as psychedelic experiences or "trips") and a perceived "expansion of consciousness". Also referred to as classic halluci ...

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 specifically the analogue of LSD in which one of LSD's

carbon Carbon () is a chemical element; it has chemical symbol, symbol C and atomic number 6. It is nonmetallic and tetravalence, tetravalent—meaning that its atoms are able to form up to four covalent bonds due to its valence shell exhibiting 4 ...

atom Atoms are the basic particles of the chemical elements. An atom consists of a atomic nucleus, nucleus of protons and generally neutrons, surrounded by an electromagnetically bound swarm of electrons. The chemical elements are distinguished fr ...

s in the ergoline

ring system A ring system is a disc or torus orbiting an astronomical object that is composed of solid material such as dust, meteoroids, planetoids, moonlets, or stellar objects. Ring systems are best known as planetary rings, common components of sate ...

, the carbon at position 4, has been removed. This in turn renders the DEIMDHPCA molecule more flexible and makes it a partially rigid indolic

phenethylamine Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine, which acts as a central nervous system stimulant in humans. In the brain, phenethylamine regulates monoamine neurotransmission by binding to trace ami ...

-containing compound rather than an ergoline. DEIMDHPCA is known to be a highly potent

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-HT₂ 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 ...

similarly to LSD and to produce

psychoplastogen Psychoplastogens, also known as neuroplastogens, are a group of Small molecule#Drugs, small molecule drugs that produce rapid and sustained effects on neuronal structure and function, intended to manifest therapeutic benefit after a single admin ...

ic effects. LSD and DEIMDHPCA chemical structures

Pharmacology

Like LSD, the drug is known to be a highly potent

5-HT_2A and 5-HT_2C receptor

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 ...

''. Its affinities () are in the ranges of 10–100nM for the serotonin 5-HT_2A receptor and 100–1,000nM for the serotonin 5-HT_2C receptor, while its activational potencies () are less than 10nM for the serotonin 5-HT_2A receptor and in the range of 10–100nM for the serotonin 5-HT_2C receptor. DEIMDHPCA was the most potent serotonin 5-HT_2A receptor agonist of 27evaluated ergoline-like compounds. In line with its serotonin 5-HT_2A receptor agonism, and similarly to LSD and other psychedelics, DEIMDHPCA has been found to produce

ic effects on

neurite A neurite or neuronal process refers to any projection from the cell body of a neuron. This projection can be either an axon or a dendrite. The term is frequently used when speaking of immature or developing neurons, especially of cells in culture ...

growth ''in vitro''. Many serotonin 5-HT_2A receptor agonists, for instance LSD, produce

psychedelic Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary mental states (known as psychedelic experiences or "trips") and a perceived "expansion of consciousness". Also referred to as classic halluci ...

effects in humans. The publication that reported DEIMDHPCA specifically pertained to psychoplastogenic ergoline-like compounds with no or reduced

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 activity for potential therapeutic use. However, the hallucinogenic-related properties of DEIMDHPCA and the other reported compounds, for instance their effects in the

head-twitch response The head-twitch response (HTR), also sometimes known as wet dog shakes (WDS) in rats, is a rapid side-to-side head movement that occurs in mice and rats in association with serotonin 5-HT2A receptor activation. Serotonergic psychedelics like lys ...

(HTR)

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 ...

, were not individually described. As such, it remains unclear whether or not DEIMDHPCA could have psychedelic effects in humans.

History

DEIMDHPCA was first described in the literature by 2021. It has been

patent A patent is a type of intellectual property that gives its owner the legal right to exclude others from making, using, or selling an invention for a limited period of time in exchange for publishing an sufficiency of disclosure, enabling discl ...

ed by Delix Therapeutics.

Related compounds

Other related compounds in which one or more other carbons have been removed from the

LSD Lysergic acid diethylamide, commonly known as LSD (from German ; often referred to as acid or lucy), is a semisynthetic, hallucinogenic compound derived from ergot, known for its powerful psychological effects and serotonergic activity. I ...

's ergoline ring system to produce simplified and less-rigid phenethylamines and

tryptamine Tryptamine is an indolamine metabolite of the essential amino acid tryptophan. The chemical structure is defined by an indole—a fused benzene and pyrrole ring, and a 2-aminoethyl group at the second carbon (third aromatic atom, with the firs ...

s include ''N''-DEAOP-NMT and

NDTDI NDTDI, also known as 8,10-seco-LSD, is a tricyclic tryptamine derivative which is thought to act as a serotonin receptor agonist, though its pharmacology has not been studied in detail. It is a structurally simplified analogue of the psychedeli ...

. ''N''-DEAOP-NMT is the analogue of LSD in which the carbon atoms at positions 9 and 10 of the ergoline ring system have been removed to make a fully non-rigid tryptamine, while NDTDI is the analogue of LSD in which only the carbon at position 9 has been removed to make a rigid

tricyclic Tricyclics are cyclic chemical compounds that contain three fused rings of atoms. Many compounds have a tricyclic structure, but in pharmacology, the term has traditionally been reserved to describe heterocyclic drugs. They include antidepr ...

tryptamine. ''N''-DEAOP-NMT has been found to produce LSD-like effects in rodents, while NDTDI has been encountered as a novel

recreational Recreation is an activity of leisure, leisure being discretionary time. The "need to do something for recreation" is an essential element of human biology and psychology. Recreational activities are often done for enjoyment, amusement, or plea ...

and

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. ...

and made illegal in parts of

Europe Europe is a continent located entirely in the Northern Hemisphere and mostly in the Eastern Hemisphere. It is bordered by the Arctic Ocean to the north, the Atlantic Ocean to the west, the Mediterranean Sea to the south, and Asia to the east ...

. The analogue of DEIMDHPCA without the

ethyl group In organic chemistry, an ethyl group (abbr. Et) is an alkyl substituent with the formula , derived from ethane (). ''Ethyl'' is used in the International Union of Pure and Applied Chemistry The International Union of Pure and Applied ...

s on the

amide In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a chemical compound, compound with the general formula , where R, R', and R″ represent any group, typically organyl functional group, groups or hydrogen at ...

has been described. In addition, DEIMDHPCA's analogue without the amide ethyl groups and with a

phenyl ring In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula , and is often represented by the symbol Ph (archaically φ) or Ø. The phenyl group is closely related to benzene and can be viewed as a benzene ...

instead of the

ring has been described. Their activities were not reported. WXVL BT0793LQ2118 structure

WXVL_BT0793LQ2118, an analogue of DEIMDHPCA lacking the ''N'',''N''-diethyl-carboxamide moiety and with a

fluorine Fluorine is a chemical element; it has Chemical symbol, symbol F and atomic number 9. It is the lightest halogen and exists at Standard temperature and pressure, standard conditions as pale yellow Diatomic molecule, diatomic gas. Fluorine is extre ...

at the 6-position, has been reported. It was identified via ''

in silico In biology and other experimental sciences, an ''in silico'' experiment is one performed on a computer or via computer simulation software. The phrase is pseudo-Latin for 'in silicon' (correct ), referring to silicon in computer chips. It was c ...

'' screening of 1.6billion molecules for serotonin 5-HT_2A receptor agonism with

AlphaFold2 AlphaFold is an artificial intelligence (AI) program developed by DeepMind, a subsidiary of Alphabet Inc., Alphabet, which performs Protein structure prediction, predictions of protein structure. It is designed using deep learning techniques. Alp ...

. Following identification, the drug was assessed and found to be a potent

5-HT_2A, 5-HT_2B, and 5-HT_2C receptor

References

External links

DEIMPCA - Isomer Design
{{Ergolines 5-HT2A agonists 5-HT2C agonists Carboxamides Diethylamino compounds Tetrahydropyridines Experimental drugs Indoles Methyl compounds Partial ergolines Serotonin receptor agonists

Pharmacology

History

Related compounds

See also

References

External links