DOAM was first synthesized byAlexander Shulgin.[1] In his bookPiHKAL (Phenethylamines i Have Known And Loved), the minimumdosage is listed as 10mgorally and theduration is 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 10mg orally and to behallucinogenic at a dose of 40mg, with about 10-fold higherpotency thanmescaline.[2][3][4] In any case, it shows far lower psychedelic potency than other DOx drugs such asDOM.[2][3] No qualitative description of its effects at hallucinogenic doses is available.[3][1]
DOAM fails to substitute forDOM in rodentdrug discrimination tests, producing up to 35% responding followed up behavioral disruption at higher doses.[6][7][8] It was also unable to antagonize the DOM stimulus at the assessed doses, and behavioral disruption at higher doses prevented further assessment.[9]
As the 4-alkyl chain length in DOx is increased from shorter homologues such asDOM,DOET andDOPR which are all potent hallucinogens, the serotonin5-HT2 receptorbinding affinity increases, rising to a maximum withDOHx before falling again with even longer chains. Compounds with sufficiently long chains, such as DOAM, or with bulky groups such asDOTB, fail to produce full psychedelic-like effects in animals and/or humans. These findings suggest that such compounds may act as low-efficacypartial agonists orantagonists of the serotonin 5-HT2A receptor.[10][7][11][12]
^abBraun 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 fromthe 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.
^abcShulgin 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. [...]
^abSeggel MR, Yousif MY, Lyon RA, Titeler M,Roth BL, Suba EA, et al. (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.
^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.
^Shulgin AT, Dyer DC (December 1975). "Psychotomimetic phenylisopropylamines. 5. 4-Alkyl-2,5-dimethoxyphenylisopropylamines".Journal of Medicinal Chemistry.18 (12):1201–4.doi:10.1021/jm00246a006.PMID1195275.
^Dowd CS, Herrick-Davis K, Egan C, DuPre A, Smith C, Teitler M, et al. (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.
