3-Aminochroman

3-Aminochroman
Names
IUPAC name
3,4-dihydro-2H-chromen-3-amine
Other names
  • 3-aminochroman
  • 3-AH
  • DHABP
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C9H11NO/c10-8-5-7-3-1-2-4-9(7)11-6-8/h1-4,8H,5-6,10H2
    Key: SVWDNDQOXZHBRM-UHFFFAOYSA-N
  • C1C(COC2=CC=CC=C21)N
Properties
C9H11NO
Molar mass 149.193 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

3-Aminochroman (3-AC or 3-AH), also known as 3,4-dihydro-3-amino-2H-1-benzopyran (DHABP), is a chroman derivative, a hard cyclized amphetamine structural analogue, and a chemically important reagent in pharmaceutical synthesis; most derivatives of 3-aminochroman are powerful psychoactive substances, 3-aminochroman exhibits relatively moderate to low biological activity.[1][2][3][4][5][6]

Derivatives

  • 3-Dipropylamino-5-hydroxychroman (5-OH-DPAC)
  • Ebalzotan
  • Aminochromanone
  • DPAC
  • 6,7-Dihydroxy-3-aminochroman (6,7-diOH-3-AC)

See also

References

  1. ^ Chandrasekhar, D. Balaji; Tsay, Shwu-Chen; Pradhan, Tapan K.; Hwu, Jih Ru (2017-06-02). "Syntheses of Chroman-2-ones and α-Amino Acids through a Diastereoselective Domino Reaction". The Journal of Organic Chemistry. 82 (11): 5524–5537. doi:10.1021/acs.joc.7b00260. ISSN 1520-6904. PMID 28431207.
  2. ^ Zhou, Dahui; Hatzenbuhler, Nicole T.; Gross, Jonathan L.; Harrison, Boyd L.; Evrard, Deborah A.; Chlenov, Michael; Golembieski, Jeannette; Hornby, Geoffrey; Schechter, Lee E.; Smith, Deborah L.; Andree, Terrance H.; Stack, Gary P. (2007-06-01). "Novel pyridyl-fused 3-amino chroman derivatives with dual action at serotonin transporter and 5-HT1A receptor". Bioorganic & Medicinal Chemistry Letters. 17 (11): 3117–3121. doi:10.1016/j.bmcl.2007.03.049. ISSN 0960-894X. PMID 17407811.
  3. ^ Hatzenbuhler, Nicole T.; Evrard, Deborah A.; Harrison, Boyd L.; Huryn, Donna; Inghrim, Jennifer; Kraml, Christina; Mattes, James F.; Mewshaw, Richard E.; Zhou, Dahui; Hornby, Geoffrey; Lin, Qian; Smith, Deborah L.; Sullivan, Kelly M.; Schechter, Lee E.; Beyer, Chad E. (2006-07-27). "Synthesis and biological evaluation of novel compounds within a class of 3-aminochroman derivatives with dual 5-HT1A receptor and serotonin transporter affinity". Journal of Medicinal Chemistry. 49 (15): 4785–4789. doi:10.1021/jm060218h. ISSN 0022-2623. PMID 16854086.
  4. ^ Hatzenbuhler, Nicole T.; Baudy, Reinhardt; Evrard, Deborah A.; Failli, Amedeo; Harrison, Boyd L.; Lenicek, Steven; Mewshaw, Richard E.; Saab, Annmarie; Shah, Uresh; Sze, Jean; Zhang, Minsheng; Zhou, Dahui; Chlenov, Michael; Kagan, Michael; Golembieski, Jeannette (2008-11-13). "Advances toward new antidepressants with dual serotonin transporter and 5-HT1A receptor affinity within a class of 3-aminochroman derivatives. Part 2". Journal of Medicinal Chemistry. 51 (21): 6980–7004. doi:10.1021/jm8007097. ISSN 1520-4804. PMID 18834188.
  5. ^ Holmberg, Pär; Sohn, Daniel; Leideborg, Robert; Caldirola, Patrizia; Zlatoidsky, Pavel; Hanson, Sverker; Mohell, Nina; Rosqvist, Susanne; Nordvall, Gunnar; Johansson, Anette M.; Johansson, Rolf (2004-07-29). "Novel 2-aminotetralin and 3-aminochroman derivatives as selective serotonin 5-HT7 receptor agonists and antagonists". Journal of Medicinal Chemistry. 47 (16): 3927–3930. doi:10.1021/jm0498102. ISSN 0022-2623. PMID 15267230.
  6. ^ Holmberg, Pär; Sohn, Daniel; Leideborg, Robert; Caldirola, Patrizia; Zlatoidsky, Pavel; Hanson, Sverker; Mohell, Nina; Rosqvist, Susanne; Nordvall, Gunnar; Johansson, Anette M.; Johansson, Rolf (2004-07-29). "Novel 2-aminotetralin and 3-aminochroman derivatives as selective serotonin 5-HT7 receptor agonists and antagonists". Journal of Medicinal Chemistry. 47 (16): 3927–3930. doi:10.1021/jm0498102. ISSN 0022-2623. PMID 15267230.
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