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 ...
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 s ...
. DOAM was first synthesized by
Alexander Shulgin. 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,
DOET and
DOPR which are all potent hallucinogens, the 5-HT
2 binding affinity 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 and are thus
antagonists or
partial agonists at the 5-HT
2A receptor.
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See also
* 2,5-Dimethoxy-4-Substituted Amphetamine
4-Substituted-2,5-dimethoxyamphetamines (DO''x'') is a chemical class of substituted amphetamine derivatives featuring methoxy groups at the 2- and 5- positions of the phenyl ring, and a substituent such as alkyl or halogen at the 4- position of ...
s
References
External links
DOAM Entry in ''PiHKAL''
DOAM Entry in PiHKAL • info
Substituted amphetamines
2,5-Dimethoxyphenethylamines
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