2,5-Dimethoxy-4-amylamphetamine

2,5-Dimethoxy-4-amylamphetamine
Names
	Preferred IUPAC name 1-(2,5-Dimethoxy-4-pentylphenyl)propan-2-amine
	Other names DOAM;; 2,5-Dimethoxy-4-amyl-amphetamine;; 2,5-Dimethoxy-4-amyl-1-ethyl-(alpha-methyl)amine
Identifiers
CAS Number	63779-90-8 ;
3D model (JSmol)	Interactive image; Interactive image;
Abbreviations	DOAM
ChEMBL	ChEMBL161416 ;
ChemSpider	10440619 ;
PubChem CID	12262512;
UNII	N80EWL36CB ;
CompTox Dashboard (EPA)	DTXSID50482958 ;
	InChI 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 Key: VLJORLCVOAUUKM-UHFFFAOYSA-N ; InChI=1/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 Key: VLJORLCVOAUUKM-UHFFFAOYAN;
	SMILES CCCCCC1=CC(OC)=C(CC(C)N)C=C1OC; COc1cc(CCCCC)c(cc1CC(C)N)OC;
Properties
Chemical formula	C16H27NO2
Molar mass	265.39 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Dimethoxy-4-amylamphetamine (DOAM) is a lesser-known psychedelic drug and a substituted amphetamine. 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-HT₂ 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.^[1]^[2]^[3]^[4]

References

^ 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. PMID 1195275.
^ Seggel MR, Yousif MY, Lyon RA, Titeler M, Roth BL, Suba EA, Glennon RA (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. PMID 2308135.
^ Dowd CS, Herrick-Davis K, Egan C, DuPre A, Smith C, Teitler M, Glennon RA (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. PMID 10956215.
^ Kruegel AC. Phenalkylamines and Methods of Making and Using the Same. Patent WO 2022/192781

External links

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[pmid1195275-1] 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. PMID 1195275.

[pmid2308135-2] Seggel MR, Yousif MY, Lyon RA, Titeler M, Roth BL, Suba EA, Glennon RA (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. PMID 2308135.

[pmid10956215-3] Dowd CS, Herrick-Davis K, Egan C, DuPre A, Smith C, Teitler M, Glennon RA (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. PMID 10956215.

[4] Kruegel AC. Phenalkylamines and Methods of Making and Using the Same. Patent WO 2022/192781

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See also

References

External links