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| Other names | DOAM; 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 class | Serotonin5-HT2 receptoragonist;Serotonin 5-HT2A receptor agonist;Serotonergic psychedelic;Hallucinogen |
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| Duration of action | Unknown[1] |
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| Formula | C16H27NO2 |
| Molar mass | 265.397 g·mol−1 |
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2,5-Dimethoxy-4-amylamphetamine (DOAM), also known as2,5-dimethoxy-4-pentylamphetamine, is apsychedelic drug of thephenethylamine,amphetamine, andDOx families related toDOM.[1][2] It is thederivative of DOM in which themethyl group at the 4 position has been replaced with anamyl (pentyl)group.[1][2] The drug is takenorally.[1]
It is aserotonin receptor agonist, including of theserotonin5-HT2A receptor.[2] The drug produces weak and mixed psychedelic-like effects in animals.[2][3][4][5]
DOAM was first described in thescientific literature byAlexander Shulgin and colleagues in 1975.[6] Subsequently, it was described in greater detail by Shulgin in his 1991 bookPiHKAL (Phenethylamines I Have Known and Loved).[1]
In his bookPiHKAL (Phenethylamines I Have Known and Loved),Alexander Shulgin lists the dose of DOAM as >10 mgorally and itsduration 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 behallucinogenic at a dose of 40 mg, with about 10-fold higherpotency thanmescaline.[7][8][6] In any case, it shows far lower psychedelic potency than other DOx drugs such asDOM.[7][8] No qualitative description of its effects at hallucinogenic doses is available.[8][1]
DOAM has been found to be a moderate- to high-efficacypartial agonist of theserotonin5-HT2A receptor.[2][9] It also shows loweraffinity for the serotonin5-HT2B and5-HT2C receptors, whereas it has very low affinity for the serotonin5-HT1A receptor.[2][9] The drug is afull agonist of the serotonin 5-HT2B and 5-HT2C receptors.[2] It is mostpotent 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 lowpotency as a humantrace amine-associated receptor 1 (TAAR1) agonist.[2][9] It does not bind to themonoamine transporters.[2][9] Other receptor interactions have also been described.[2]
The drug produces thehead-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 rodentdrug 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 includehyperlocomotion at lower doses,hypolocomotion at higher doses, andhypothermia at higher doses.[2]
As the 4-alkyl chain length in DOx is increased from shorter homologues such as DOM,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, 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]
DOAM crosses theblood–brain barrier in rodents.[2]
Thechemical synthesis of DOAM has been described.[1]
Analogues of DOAM include2,5-dimethoxyamphetamine (2,5-DMA),DOM,DOET,DOPR,DOBU, andDOHx, among others.[1][2]
DOAM was first described in thescientific literature byAlexander Shulgin and colleagues in 1975.[6] Subsequently, it was described in greater detail by Shulgin in his 1991 bookPiHKAL (Phenethylamines I Have Known and Loved).[1]
DOAM is acontrolled substance inCanada under phenethylamine blanket-ban language.[13]
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.
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.
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. [...]
