DOI-NBOMe, or NBOMe-DOI, also known as ''N''-(2-methoxybenzyl)-4-iodo-2,5-dimethoxyamphetamine, is 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-HT_2A 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 ...

and possible

psychedelic drug 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 halluc ...

of the phenetylamine, DOx, and

25-NB The 25-NB (25''x''-NB''x'') series, or NBOMe series, also known as the ''N''-benzylphenethylamines, is a family of serotonergic psychedelics. They are substituted phenethylamines and were derived from the 2C family. The most commonly encountere ...

(NBOMe) families. It is the ''N''-(2-methoxybenzyl)

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 ...

of DOI and the

amphetamine Amphetamine (contracted from Alpha and beta carbon, alpha-methylphenethylamine, methylphenethylamine) is a central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, an ...

(i.e., α-methyl) analogue of

25I-NBOMe 25I-NBOMe, also known as 2C-I-NBOMe, Cimbi-5, and shortened to "25I", is a psychedelic drug of the phenethylamine, 2C, and NBOMe (25-NB) families. Since 2010, it has circulated in the recreational drug scene, often misrepresented as LSD. It is ...

Pharmacology

The drug is a potent serotonin 5-HT_2A 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 ...

, 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 ...

(K_i) of 0.78 to 1.08nM, an of 36.1nM, and an of 43% in the employed

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 ...

. As an agonist of the serotonin 5-HT_2A receptor, DOI-NBOMe had about half the affinity and potency of DOI and a little more than half the efficacy in comparison ''

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 ...

'' (with DOI having a K_i of 0.58–0.64nM, an of 19.2nM, and an of 77%). Compared to 25I-NBOMe, the corresponding NBOMe analogue of

2C-I 2C-I, also known as 2,5-dimethoxy-4-iodophenethylamine, is a phenethylamine of the 2C family with psychedelic effects. It was first synthesized by Alexander Shulgin, and is described in Shulgin's book ''PiHKAL'' (1991). The substance is con ...

, DOI-NBOMe had about 14.4-fold lower potency as a serotonin 5-HT_2A receptor agonist and slightly more than half the activational efficacy. Whereas the potency of 2Cs can be dramatically increased by ''N''-(2-methoxybenzyl)

substitution Substitution may refer to: Arts and media *Substitution (poetry), a variation in poetic scansion * Substitution (theatre), an acting methodology Music *Chord substitution, swapping one chord for a related one within a chord progression *Tritone ...

, this has not been the case with the DOx series of psychedelics, where activity has been negatively impacted. Besides the serotonin 5-HT_2A receptor, DOI-NBOMe has also been shown to bind to the serotonin 5-HT_2C receptor, with an affinity (K_i) of 21.0nM. This was about 33-fold lower than the affinity of DOI. As such, DOI-NBOMe appears to show increased

selectivity Selectivity may refer to: Psychology and behaviour * Choice, making a selection among options * Discrimination, the ability to recognize differences * Socioemotional selectivity theory, in social psychology Engineering * Selectivity (radio), a ...

for the serotonin 5-HT_2A receptor over the serotonin 5-HT_2C receptor compared to DOI. For comparison, 25I-NBOMe had increased affinities for both the serotonin 5-HT_2A receptor and to a lesser extent the serotonin 5-HT_2C receptor compared to 2C-I.

History

DOI-NBOMe 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 Ralf Heim by 2003. However, Heim only synthesized DOI-NBOMe without reporting its

pharmacology Pharmacology is the science of drugs and medications, including a substance's origin, composition, pharmacokinetics, pharmacodynamics, therapeutic use, and toxicology. More specifically, it is the study of the interactions that occur betwee ...

. The pharmacological interactions of DOI-NBOMe were subsequently reported by Michael Braden and colleagues, from the lab of

David E. Nichols David Earl Nichols (born December 23, 1944, Covington, Kentucky) is an American pharmacologist and medicinal chemist. Previously the Robert C. and Charlotte P. Anderson Distinguished Chair in Pharmacology at Purdue University, Nichols has worke ...

, by 2006.

References

External links

DOI-NBOMe - Isomer Design
{{Phenethylamines 5-HT2A agonists 25-NB (psychedelics) Iodobenzene derivatives DOx (psychedelics) 2-Methoxyphenyl compounds Serotonin receptor modulators

Pharmacology

History

See also

References

External links