Dimethoxy-4-amylamphetamine (DOAM) is a lesser-known

psychedelic drug Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary states of consciousness (known as psychedelic experiences or "trips").Pollan, Michael (2018). ''How to Change Your Mind: What the New Science o ...

and a

substituted amphetamine Substituted amphetamines are a class of compounds based upon the amphetamine structure; it includes all derivative compounds which are formed by replacing, or substituting, one or more hydrogen atoms in the amphetamine core structure with sub ...

. DOAM was first synthesized by

Alexander Shulgin Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American medicinal chemist, biochemist, organic chemist, pharmacologist, psychopharmacologist, and author. He is credited with introducing 3,4-methylenedioxymethamph ...

. In his book '' PiHKAL (Phenethylamines i Have Known And Loved)'', the minimum dosage is listed as 10 mg, and the duration is unknown. DOAM produces a bare threshold and tenseness. As the 4-alkyl chain length is increased from shorter homologues such as

DOM Dom or DOM may refer to: People and fictional characters * Dom (given name), including fictional characters * Dom (surname) * Dom La Nena (born 1989), stage name of Brazilian-born cellist, singer and songwriter Dominique Pinto * Dom people, an et ...

DOET 2,5-Dimethoxy-4-ethylamphetamine (DOET, DOE, Hecate) is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was first synthesized by Alexander Shulgin, and was described in his book '' PiHKAL'' (''Phenethylamines i Hav ...

and

DOPR 2,5-Dimethoxy-4-propylamphetamine (DOPR) is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was first synthesized by Alexander Shulgin Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was a ...

which are all potent hallucinogens, the 5-HT₂

binding affinity In biochemistry and pharmacology, a ligand is a substance that forms a complex with a biomolecule to serve a biological purpose. The etymology stems from ''ligare'', which means 'to bind'. In protein-ligand binding, the ligand is usually a mol ...

increases, rising to a maximum with the 4-(''n''-hexyl) derivative before falling again with even longer chains, but compounds with chain length longer than ''n''-propyl, or with other bulky groups such as isopropyl, ''t''-butyl or γ-phenylpropyl at the 4- position, fail to substitute for hallucinogens in animals or produce hallucinogenic effects in humans, suggesting these have low

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 pragmatic clinical trial#Efficacy versu ...

and are thus

antagonists An antagonist is a character in a story who is presented as the chief foe of the protagonist. Etymology The English word antagonist comes from the Greek ἀνταγωνιστής – ''antagonistēs'', "opponent, competitor, villain, enemy, riv ...

partial agonists An agonist is a chemical that activates a receptor to produce a biological response. Receptors are cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an antagonist blocks the action of the ago ...

at the 5-HT_2A receptor.Kruegel AC. Phenalkylamines and Methods of Making and Using the Same. Patent WO 2022/192781
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References

External links

DOAM Entry in ''PiHKAL''

DOAM Entry in PiHKAL • info
Substituted amphetamines 2,5-Dimethoxyphenethylamines {{Psychoactive-stub

See also

References

External links