DOAM was first described in the scientific literature by Alexander Shulgin and colleagues in 1975. Subsequently, it was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).
Use and effects
In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists the dose of DOAM as greater than 10mg orally and its duration as unknown. DOAM was reported to produce a bare threshold and tenseness. In other publications however, DOAM has been said to produce threshold effects at 5 to 10mg orally and to be hallucinogenic at a dose of 40mg orally, with about 10-fold higher potency than mescaline. In any case, it shows far lower psychedelic potency than other DOx drugs such as DOM. No qualitative description of its effects at hallucinogenic doses is available.
DOAM has been found to be a moderate- to high-efficacypartial agonist of the serotonin5-HT2A receptor. 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. The drug is a full agonist of the serotonin 5-HT2B and 5-HT2C receptors. 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. DOAM shows very low potency as a human trace amine-associated receptor 1 (TAAR1) agonist. It does not bind to the monoamine transporters. Other receptor interactions have also been described.
The drug produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents. However, it produces only a weak head-twitch response and is less potent and much less efficacious than DOM in this regard. 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. It was also unable to antagonize the DOM stimulus at the assessed doses, and behavioral disruption at higher doses prevented further assessment. Other effects of DOAM in rodents include hyperlocomotion at lower doses, hypolocomotion at higher doses, and hypothermia at higher doses.
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 receptorbinding 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.
DOAM was first described in the scientific literature by Alexander Shulgin and colleagues in 1975. Subsequently, it was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).
123Seggel MR, Yousif MY, Lyon RA, Titeler M, Roth BL, Suba EA, etal. (March 1990). "A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors". Journal of Medicinal Chemistry. 33 (3): 1032–6. doi:10.1021/jm00165a023. PMID2308135. For example, using rats trained to discriminate DOM from saline, ED,, values for stimulus generalization are significantly correlated with 5-HT2 affinity. However, some of the compounds included in the present study (e.g., In and Io) possess a high affinity for the 5-HT2 sites but do not result in stimulus generalization.
12Braun U, Braun G, Jacob P, Nichols DE, Shulgin AT (1978). "Mescaline analogs: substitutions at the 4-position"(PDF). NIDA Res Monogr (22): 27–37. PMID101882. Archived from the original(PDF) on August 5, 2023. TABLE II RELATIVE POSTENCIES IN MAN OF DIMETHOXYPHENYLISOPROPYLAMINE PSYCHOTOMIMETICS WITH VARIOUS SUBSTITUENTS ON THE 4-POSITION [...] Name: DOBU. Potency (total dose mg/man): 10 mg (e). Name: DOTB. Potency (total dose mg/man): >25 mg (d,f). Name: DOAM. Potency (total dose mg/man): 40 mg (e). [...] REFERENCES FOR TABLE II: [...] d. Shulgin, A.T., and Nichols, D.E. In: Stillman, R., and Willette, R. eds. Psychopharmacology of Hallucinogens. New York: Pergamon Press, 1978. e. Shulgin, A.T., and Dyer, D.C. J Med Chem, 18:1201, 1975. f. A > symbol indicates the absence of any activity at the stated dosage.
123Shulgin AT (1978). "Psychotomimetic Drugs: Structure-Activity Relationships". In Iversen LL, Iversen SD, Snyder SH (eds.). Stimulants. Boston, MA: Springer US. pp.243–333. doi:10.1007/978-1-4757-0510-2_6. ISBN978-1-4757-0512-6. 3.4.11. 2,5-Dimethoxy-4-amylphenylisopropylamine: The last member of this series of homologs is 2,5-dimethoxy-4-amylphenylisopropylamine (77, DOAM). As will be seen below, it has been studied both in behavioral tests and in biochemical systems, and in both it appears to be of substantially reduced potency compared with its two immediately lower homologs. Limited human evaluation has provided the same results. Threshold effects are noticed at levels of 5-10 mg orally, and the compound has a stated effective potency of only 10 times that of mescaline (Shulgin and Dyer, 1975). No qualitative description of its intoxication syndrome at effective levels can be made from the limited experimental data available. [...]
↑Glennon RA, Seggel MR (14 November 1989). "Interaction of Phenylisopropylamines with Central 5-HT2 Receptors: Analysis by Quantitative Structure—Activity Relationships". Probing Bioactive Mechanisms. Vol.413. Washington, DC: American Chemical Society. pp.264–280. doi:10.1021/bk-1989-0413.ch018. ISBN978-0-8412-1702-7.
↑Dowd CS, Herrick-Davis K, Egan C, DuPre A, Smith C, Teitler M, etal. (August 2000). "1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT(2A) partial agonists". Journal of Medicinal Chemistry. 43 (16): 3074–84. doi:10.1021/jm9906062. PMID10956215.
