Chemistry:2,5-Dimethoxy-4-hydroxyamphetamine

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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

  • DOx (psychedelics)

References

  1. ↑ Trachsel, D.; Lehmann, D.; Enzensperger, C. (2013) (in de). Phenethylamine: von der Struktur zur Funktion. Nachtschatten-Science (1 ed.). Solothurn: Nachtschatten-Verlag. ISBN 978-3-03788-700-4. OCLC 858805226. https://books.google.com/books?id=-Us1kgEACAAJ. 
  2. ↑ Shulgin, A.; Manning, T.; Daley, P.F. (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0. 
  3. ↑ 3.0 3.1 3.2 3.3 3.4 "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. November 2008. doi:10.1021/jm800771x. 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.". 
  4. ↑ 4.0 4.1 4.2 4.3 4.4 4.5 "Interaction of Phenylisopropylamines with Central 5-HT2 Receptors". Probing Bioactive Mechanisms. ACS Symposium Series. 413. 1989. pp. 264–280. doi:10.1021/bk-1989-0413.ch018. ISBN 978-0-8412-1702-7. 
  5. ↑ 5.0 5.1 5.2 5.3 5.4 5.5 5.6 "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. March 1990. doi:10.1021/jm00165a023. PMID 2308135. 
  6. ↑ "Quantitative structure-activity relationships in the 2,4,5-ring substituted phenylisopropylamines". NIDA Res Monogr (22): 199–217. 1978. PMID 101881. 



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