Β-MeO-DOB

β-MeO-DOB
Clinical data
Other namesβ-Methoxy-DOB; 3C-BOB; β-Methoxy-4-bromo-2,5-dimethoxyamphetamine; AL-37662; AL37662
Drug classPeripherally selective serotonin 5-HT2A receptor agonist
ATC code
  • None
Identifiers
  • 1-(4-bromo-2,5-dimethoxyphenyl)-1-methoxypropan-2-amine
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC12H18BrNO3
Molar mass304.184 g·mol−1
3D model (JSmol)
  • CC(C(C1=CC(=C(C=C1OC)Br)OC)OC)N
  • InChI=1S/C12H18BrNO3/c1-7(14)12(17-4)8-5-11(16-3)9(13)6-10(8)15-2/h5-7,12H,14H2,1-4H3
  • Key:JZRYUHHXNUHBTB-UHFFFAOYSA-N

β-MeO-DOB, also known as 3C-BOB or β-methoxy-4-bromo-2,5-dimethoxyamphetamine and by the developmental code name AL-37662 (specifically the (1R,2R)- enantiomer), is an experimental putative psychedelic drug which has a markedly reduced ability to cross the blood–brain barrier. The compound was developed and evaluated as a peripheral agent for topical application (in the form of eye drops) with the aim of reducing intraocular pressure in glaucoma.

Interactions

Pharmacology

Pharmacodynamics

AL-37662 acts as a full 5-HT2A receptor agonist with an affinity (Ki) of 0.3 nM; it successfully reduced intraocular pressure by 20 to 27% when administered topically. If administered directly into the brain or taken by any means other than as eye drops in high doses, it may cause psychedelic effects; however, when administered as therapeutic eye drops in microdoses (300 µg), AL-37662 did not produce any effects.

Chemistry

β-MeO-DOB is a mixture of multiple enantiomers. The (1R,2R)- enantiomer is AL-37662.

Synthesis

The chemical synthesis of β-MeO-DOB has been described.

Analogues

Analogues of β-MeO-DOB include β-HO-DOB (β-hydroxy-DOB; 3C-BOHB), βk-DOB (β-keto-DOB), and BOB (β-methoxy-2C-B), among others.

History

AL-37662 was first described in the scientific literature by Richard Glennon and colleagues in 2004.

See also

References

  1. 1 2 3 4 5 6 7 Glennon RA, Bondarev ML, Khorana N, Young R, May JA, Hellberg MR, et al. (November 2004). "Beta-oxygenated analogues of the 5-HT2A serotonin receptor agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane". Journal of Medicinal Chemistry. 47 (24): 6034–6041. doi:10.1021/jm040082s. PMID 15537358.
  2. 1 2 Blaazer AR, Smid P, Kruse CG (September 2008). "Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT(2A) receptors". ChemMedChem. 3 (9): 1299–1309. doi:10.1002/cmdc.200800133. PMID 18666267.
  3. ↑ Nichols DE (2017). "Chemistry and Structure–Activity Relationships of Psychedelics". Current Topics in Behavioral Neurosciences. Berlin, Heidelberg: Springer Berlin Heidelberg. pp. 1–43. ISBN 978-3-662-55878-2.
  4. ↑ Lemaire D, Jacob P, Shulgin AT (August 1985). "Ring-substituted beta-methoxyphenethylamines: a new class of psychotomimetic agents active in man". The Journal of Pharmacy and Pharmacology. 37 (8): 575–577. doi:10.1111/j.2042-7158.1985.tb03072.x. PMID 2864422.