2,5-Dimethoxy-4-hexylamphetamine (DOHx or DOHE) is a 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 ...

serotonin receptor 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 ...

modulator Signal modulation is the process of varying one or more properties of a periodic waveform in electronics and telecommunication for the purpose of transmitting information. The process encodes information in form of the modulation or message ...

of the

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 ...

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 ...

, and DOx families.

Pharmacology

DOHx has shown the highest

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 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-HT_2A and 5-HT_2C receptors of any other assessed DOx drug in multiple studies. In one study, its affinities for the human serotonin 5-HT₂ receptors were 0.1nM for the 5-HT_2A receptor, 30nM for the 5-HT_2B receptor, and 0.7nM for 5-HT_2C receptor. In the case of the serotonin 5-HT_2A receptor, this was 6- to 14-fold higher than

DOB DOB or Dob often refers to date of birth. DOB or Dob may also refer to: Biochemistry * 2,5-dimethoxy-4-bromoamphetamine, Bromo-DMA, a psychedelic drug ** Meta-DOB, related substance ** Methyl-DOB, related substance * HLA-DOB, human gene Organiz ...

, DOI, and

DOC DOC, Doc, doc or DoC may refer to: People and characters * Doc, an abbreviation of doctor * Doc (nickname) * Doc (mascot), the Towson University mascot Persons * The D.O.C., American rapper (born 1968) * Doc Gallows (born 1983), ring nam ...

and was 9-fold higher than

DOPR 2,5-Dimethoxy-4-propylamphetamine (DOPR) is a psychedelic drug of the phenethylamine, amphetamine, and DOx families. It was first synthesized by Alexander Shulgin, and was described in his book ''PiHKAL'' (''Phenethylamines i Have Known And Lov ...

. In another study, DOHx showed 25-fold higher affinity for the serotonin 5-HT_2A receptor than DOM or

DOET 2,5-Dimethoxy-4-ethylamphetamine (DOET) is a psychedelic drug of the phenethylamine, amphetamine, and DOx families. It is closely related to DOM and is a synthetic analogue of the naturally occurring phenethylamine psychedelic mescaline. The ...

, 23- to 28-fold higher affinity than DOPR and DOBU, and 2.8-fold higher affinity than DOAM. Conversely, it showed only slightly higher or roughly the same affinity for the receptor relative to DOCT (2.5nM vs. 3.0nM, respectively). In contrast to many other DOx drugs, DOHx, as well as related drugs like DOCT, have been found to act as serotonin 5-HT₂ receptor

antagonist An antagonist is a character in a story who is presented as the main enemy or rival of the protagonist and is often depicted as a villain.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 ...

s, and hence would not be expected to be

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 ...

s. In accordance, DOHx, DOCT, and other related drugs do not produce DOM-like effects in rodent

drug discrimination Drug discrimination (DD) is a technique in behavioral neuroscience used to evaluate the discriminative stimulus properties or interoceptive cues of psychoactive drugs. In drug discrimination, a subject is trained on a training drug, and then i ...

tests. DOHx has also been assessed and found to act as a

silent antagonist A receptor antagonist is a type of receptor ligand or drug that blocks or dampens a biological response by binding to and blocking a receptor rather than activating it like an agonist. Antagonist drugs interfere in the natural operation of recep ...

of the serotonin 5-HT_2B receptor ( = 0%).

Chemistry

DOHx is part of the series of 4-

alkyl In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term ''alkyl'' is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of . A cycloalkyl group is derived from a cy ...

ated DOx drugs that includes DOM (methyl),

(ethyl),

(propyl),

DOBU 2,5-Dimethoxy-4-butylamphetamine (DOBU) is a lesser-known serotonin receptor agonist and serotonergic psychedelic of the amphetamine and DOx families. Effects DOBU was first synthesized by Alexander Shulgin. In his book '' PiHKAL (Phenethylam ...

(butyl), and DOAM (amyl/pentyl), with DOHx having a hexyl

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 ...

and hence the longest alkyl

chain A chain is a serial assembly of connected pieces, called links, typically made of metal, with an overall character similar to that of a rope in that it is flexible and curved in compression but linear, rigid, and load-bearing in tension. A ...

of the preceding drugs. Following DOHx in the series are DOHP (heptyl) and then DOCT (octyl).

History

DOHx 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 at least 1989.

References

External links

DOHE - Isomer Design
{{DEFAULTSORT:Dimethoxy-4-hexylamphetamine, 2,5- 5-HT2 antagonists DOx (psychedelics) Serotonin receptor modulators