2,5-Dimethoxy-4-amylamphetamine

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DOAM
File:DOAM.svg
File:2,5-Dimethoxy-4-amylamphetamine-3D-spacefill.png
Clinical data
Other namesDOAM; 2,5-Dimethoxy-4-amylamphetamine; 4-Amyl-2,5-dimethoxyamphetamine; 2,5-Dimethoxy-4-pentylamphetamine; 4-Pentyl-2,5-dimethoxyamphetamine
Routes of
administration		Oral[1]
Drug classSerotonin 5-HT2 receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Duration of actionUnknown[1]
Identifiers
  • 1-(2,5-dimethoxy-4-pentylphenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
E number{{#property:P628}}
CompTox Dashboard (EPA)
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Chemical and physical data
FormulaC16H27NO2
Molar mass265.397 g·mol−1
3D model (JSmol)
  • CCCCCC1=CC(OC)=C(CC(C)N)C=C1OC
  • InChI=1S/C16H27NO2/c1-5-6-7-8-13-10-16(19-4)14(9-12(2)17)11-15(13)18-3/h10-12H,5-9,17H2,1-4H3 checkY
  • Key:VLJORLCVOAUUKM-UHFFFAOYSA-N checkY
  (verify)

2,5-Dimethoxy-4-amylamphetamine (DOAM), also known as 2,5-dimethoxy-4-pentylamphetamine, is a psychedelic drug of the phenethylamine, amphetamine, and DOx families related to DOM.[1][2] It is the derivative of DOM in which the methyl group at the 4 position has been replaced with an amyl (pentyl) group.[1][2] The drug is taken orally.[1]

It is a serotonin receptor agonist, including of the serotonin 5-HT2A receptor.[2] The drug produces weak and mixed psychedelic-like effects in animals.[2][3][4][5]

DOAM was first described in the scientific literature by Alexander Shulgin and colleagues in 1975.[6] Subsequently, it was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).[1]

Use and effects

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In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists the dose of DOAM as >10 mg orally and its duration as unknown.[1] DOAM was reported to produce a bare threshold and tenseness.[1] In other publications however, DOAM has been said to produce threshold effects at 5 to 10 mg orally and to be hallucinogenic at a dose of 40 mg, with about 10-fold higher potency than mescaline.[7][8][6] In any case, it shows far lower psychedelic potency than other DOx drugs such as DOM.[7][8] No qualitative description of its effects at hallucinogenic doses is available.[8][1]

Interactions

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See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

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Pharmacodynamics

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DOAM has been found to be a moderate- to high-efficacy partial agonist of the serotonin 5-HT2A receptor.[2][9] It also shows lower affinity for the serotonin 5-HT2B and 5-HT2C receptors, whereas it has very low affinity for the serotonin 5-HT1A receptor.[2][9] The drug is a full agonist of the serotonin 5-HT2B and 5-HT2C receptors.[2] It is most potent as a serotonin 5-HT2C receptor agonist, whereas it shows far lower potency as an agonist of the serotonin 5-HT2B receptor than as an agonist of the serotonin 5-HT2A and 5-HT2C receptors.[2] DOAM shows very low potency as a human trace amine-associated receptor 1 (TAAR1) agonist.[2][9] It does not bind to the monoamine transporters.[2][9] Other receptor interactions have also been described.[2]

The drug produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[2] However, it produces only a weak head-twitch response and is less potent and much less efficacious than DOM in this regard.[2] In addition, DOAM fails to substitute for DOM in rodent drug discrimination tests, producing up to 35% responding followed up behavioral disruption at higher doses.[3][4][5] It was also unable to antagonize the DOM stimulus at the assessed doses, and behavioral disruption at higher doses prevented further assessment.[10] Other effects of DOAM in rodents include hyperlocomotion at lower doses, hypolocomotion at higher doses, and hypothermia at higher doses.[2]

As the 4-alkyl chain length in DOx is increased from shorter homologues such as DOM, DOET and DOPR which are all potent hallucinogens, the serotonin 5-HT2 receptor binding affinity increases, rising to a maximum with DOHx before falling again with even longer chains. Compounds with sufficiently long chains, such as DOAM, or with bulky groups such as DOTB, have reduced or absent psychedelic-type effects in animals and/or humans, suggesting that they may have reduced agonistic activity at the serotonin 5-HT2A receptor.[2][6][4][11][12]

Pharmacokinetics

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DOAM crosses the blood–brain barrier in rodents.[2]

Chemistry

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Synthesis

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The chemical synthesis of DOAM has been described.[1]

Analogues

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Analogues of DOAM include 2,5-dimethoxyamphetamine (2,5-DMA), DOM, DOET, DOPR, DOBU, and DOHx, among others.[1][2]

History

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DOAM was first described in the scientific literature by Alexander Shulgin and colleagues in 1975.[6] Subsequently, it was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).[1]

See also

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References

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  12. ^ Patentscope. Kruegel AC. Phenalkylamines and Methods of Making and Using the Same. Patent WO 2022/192781. Retrieved 2025-05-12
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