2,5-Dimethoxy-4-hydroxyamphetamine
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| Other names | DOOH; 2,5-Dimethoxy-4-hydroxyamphetamine; 4-Hydroxy-2,5-dimethoxyamphetamine |
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| Formula | C11H17NO3 |
| Molar mass | 211.261 g·mol−1 |
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DOOH, also known as 2,5-dimethoxy-4-hydroxyamphetamine, is a chemical compound of the phenethylamine, amphetamine, and DOx families related to the psychedelic drug DOM.[1][2][3][4][5] In contrast to DOM and other DOx drugs, DOOH appears to be inactive.[3][5][4]
Pharmacology
Pharmacodynamics
DOOH showed no affinity for the serotonin 5-HT2A receptor (Ki = >50,000 nM).[3][5][4] This was in notable contrast to closely related compounds like DOM (the 4-methyl analogue) and TMA-2 (the 4-methoxy analogue) (Ki = 100 nM and 1,250 nM, respectively).[3][5][4] Hence, DOOH showed more than 40- to 500-fold lower affinity for the receptor than these analogues.[3][5][4]
Chemistry
Synthesis
The chemical synthesis of DOOH has been described.[5]
History
DOOH was first described in the scientific literature by George Anderson and colleagues by 1978.[6] Subsequently, its pharmacology was described by Richard Glennon and colleagues in 1989 and 1990.[5][4]
See also
References
- ^ Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. ISBN 978-3-03788-700-4. OCLC 858805226. Archived from the original on 21 August 2025.
- ^ Shulgin A, Manning T, Daley PF (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0.
- ^ a b c d e Runyon SP, Mosier PD, Roth BL, Glennon RA, Westkaemper RB (November 2008). "Potential modes of interaction of 9-aminomethyl-9,10-dihydroanthracene (AMDA) derivatives with the 5-HT2A receptor: a ligand structure-affinity relationship, receptor mutagenesis and receptor modeling investigation". Journal of Medicinal Chemistry. 51 (21): 6808–6828. doi:10.1021/jm800771x. PMC 3088499. PMID 18847250.
Compounds 2a-e and 2g have also been previously reported in the literature, and their syntheses are discussed elsewhere.11-13 [...] Table 1. Effects of Aromatic Substitution on 5-HT2A Receptor Affinity [...] The effects of 4-position substitution on the affinities of 1-(2,5-dimethoxy)-2-aminopropanes (DOX; 2a-e) are qualitatively similar in that each of these, with the exception of the hydroxy substituent (2g, Ki > 50000 nM), retains or enhances affinity. However, in the DOX series, the range of affinity enhancement is much greater (2d, Ki ) 2.5 nM; 2a, Ki ) 5200 nM) than for the AMDA series with a maximum range of about 2000-fold, excluding the 4-hydroxy compound (2g) that shows no measurable affinity.
- ^ a b c d e f Glennon RA, Seggel MR (1989). "Interaction of Phenylisopropylamines with Central 5-HT2 Receptors". Probing Bioactive Mechanisms. ACS Symposium Series. Vol. 413. pp. 264–280. doi:10.1021/bk-1989-0413.ch018. ISBN 978-0-8412-1702-7.
- ^ a b c d e f g Seggel 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): 1032–1036. doi:10.1021/jm00165a023. PMID 2308135.
- ^ Anderson GM, Castagnoli N, Kollman PA (1978). "Quantitative structure-activity relationships in the 2,4,5-ring substituted phenylisopropylamines". NIDA Research Monograph (22): 199–217. PMID 101881.