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{{chembox
{{chembox
| Name = 4C-B
| Name = 4C-B
| ImageFile1 = 4C-B_structure.png
| ImageFile1 = 4C-B Structure.svg
| IUPACName = 1-(2,5-Dimethoxy-4-bromophenyl)butan-2-amine
| PIN = 1-(4-Bromo-2,5-dimethoxyphenyl)butan-2-amine
| OtherNames = 4C-DOB, DOB-B
| OtherNames = 4C-DOB, DOB-B
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
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| InChI = 1S/C12H18BrNO2/c1-4-9(14)5-8-6-12(16-3)10(13)7-11(8)15-2/h6-7,9H,4-5,14H2,1-3H3
| InChI = 1S/C12H18BrNO2/c1-4-9(14)5-8-6-12(16-3)10(13)7-11(8)15-2/h6-7,9H,4-5,14H2,1-3H3
| InChIKey = QQPRORAZQWLMTQ-UHFFFAOYSA-N
| InChIKey = QQPRORAZQWLMTQ-UHFFFAOYSA-N
| CASNo = 69294-23-1
| CASNo = 69294-23-1
| ChEMBL = 365711
| PubChem = 12140147
| PubChem = 12140147
| SMILES = CCC(CC1=CC(=C(C=C1OC)Br)OC)N
| SMILES = CCC(CC1=CC(=C(C=C1OC)Br)OC)N
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| Appearance =
| Appearance =
| Density =
| Density =
| MeltingPt = 204-206
| MeltingPt = 204-206 °C
| BoilingPt =
| BoilingPt =
| Solubility = }}
| Solubility = }}
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}}
}}


'''4C-B''' (also known as '''4C-DOB''' or '''DOB-B''') is a lesser-known [[Psychedelics, dissociatives and deliriants|psychedelic drug]] which is related to [[2C-B]] and [[2,5-Dimethoxy-4-bromoamphetamine|DOB]].<ref>Standridge RT, et al. Phenylalkylamines with potential psychotherapeutic utility. 2. Nuclear substituted 2-amino-1-phenylbutanes. ''J. Med. Chem''. 1980, 23, 2, 154–162. {{doi|10.1021/jm00176a010}}</ref> It is a reasonably potent [[5-HT2A_receptor|5-HT<sub>2A</sub> receptor]] [[partial agonist]] with a K<sub>i</sub> of 7.6nM, but has relatively low efficacy (15% relative to 5-HT).<ref>Glennon RA, Bondarev ML, Khorana N, Young R, May JA, Hellberg MR, McLaughlin MA, Sharif NA. Beta-oxygenated analogues of the 5-HT2A serotonin receptor agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane. ''J Med Chem''. 2004 Nov 18;47(24):6034-41. {{doi|10.1021/jm040082s}} {{pmid|15537358}}</ref> It is briefly mentioned in [[Alexander Shulgin]]'s book [[PiHKAL|PiHKAL (Phenethylamines i Have Known And Loved)]] but was never tested by him,<ref>{{CitePiHKAL}}</ref> however it has subsequently been tested by other researchers and was found to be active in a dose range of 50-80mg with a duration of around 8 hours, though with generally milder effects than 2C-B or DOB.<ref name="Trachsel">{{cite book |author=Daniel Trachsel |author2=David Lehmann |author3=Christoph Enzensperger |name-list-style=amp |year=2013 |title=Phenethylamine: Von der Struktur zur Funktion |page=832|publisher=Nachtschatten Verlag AG |isbn=978-3-03788-700-4}}</ref>
'''4C-B''' (also known as '''4C-DOB''' or '''DOB-B''') is a lesser-known [[Psychedelics, dissociatives and deliriants|psychedelic drug]] which is related to [[2C-B]] and [[2,5-Dimethoxy-4-bromoamphetamine|DOB]].<ref name="pmid7359529">{{cite journal | vauthors = Standridge RT, Howell HG, Tilson HA, Chamberlain JH, Holava HM, Gylys JA, Partyka RA, Shulgin AT | title = Phenylalkylamines with potential psychotherapeutic utility. 2. Nuclear substituted 2-amino-1-phenylbutanes | journal = Journal of Medicinal Chemistry | volume = 23 | issue = 2 | pages = 154–62 | date = February 1980 | pmid = 7359529 | doi = 10.1021/jm00176a010 }}</ref> It is a reasonably potent [[5-HT2A_receptor|5-HT<sub>2A</sub> receptor]] [[partial agonist]] with a K<sub>i</sub> of 7.6nM, but has relatively low efficacy (15% relative to 5-HT).<ref name="pmid15537358">{{cite journal | vauthors = Glennon RA, Bondarev ML, Khorana N, Young R, May JA, Hellberg MR, McLaughlin MA, Sharif NA | title = Beta-oxygenated analogues of the 5-HT2A serotonin receptor agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane | journal = Journal of Medicinal Chemistry | volume = 47 | issue = 24 | pages = 6034–41 | date = November 2004 | pmid = 15537358 | doi = 10.1021/jm040082s }}</ref> It is briefly mentioned in [[Alexander Shulgin]]'s book [[PiHKAL|PiHKAL (Phenethylamines i Have Known And Loved)]] but was never tested by him,<ref>{{CitePiHKAL|name-list-style = vanc }}</ref> however it has subsequently been tested by other researchers and was found to be active in a dose range of 50-80mg with a duration of around 8 hours, though with generally milder effects than 2C-B or DOB.<ref name="Trachsel">{{cite book | vauthors = Trachsel D, Lehmann D, Enzensperger C |year=2013 |title=Phenethylamine: Von der Struktur zur Funktion |page=832|publisher=Nachtschatten Verlag AG |isbn=978-3-03788-700-4}}</ref>


== See also ==
== See also ==
* [[4C-T-2]]
* [[Ariadne (psychedelic)]]
* [[Ariadne (psychedelic)]]
* [[Phenethylamine]]
* [[Phenethylamine]]
* [[Psychedelics, dissociatives and deliriants]]
* [[Psychedelics, dissociatives and deliriants]]
* [[ZC-B]]


==References==
==References==
{{Reflist}}
{{Reflist}}


{{Hallucinogenic phenethylamines}}


[[Category:Substituted amphetamines]]
[[Category:Substituted amphetamines]]

Latest revision as of 18:32, 30 May 2024

4C-B
Names
Preferred IUPAC name
1-(4-Bromo-2,5-dimethoxyphenyl)butan-2-amine
Other names
4C-DOB, DOB-B
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • InChI=1S/C12H18BrNO2/c1-4-9(14)5-8-6-12(16-3)10(13)7-11(8)15-2/h6-7,9H,4-5,14H2,1-3H3
    Key: QQPRORAZQWLMTQ-UHFFFAOYSA-N
  • CCC(CC1=CC(=C(C=C1OC)Br)OC)N
Properties
C12H18BrNO2
Molar mass 288.185 g·mol−1
Melting point 204-206 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

4C-B (also known as 4C-DOB or DOB-B) is a lesser-known psychedelic drug which is related to 2C-B and DOB.[1] It is a reasonably potent 5-HT2A receptor partial agonist with a Ki of 7.6nM, but has relatively low efficacy (15% relative to 5-HT).[2] It is briefly mentioned in Alexander Shulgin's book PiHKAL (Phenethylamines i Have Known And Loved) but was never tested by him,[3] however it has subsequently been tested by other researchers and was found to be active in a dose range of 50-80mg with a duration of around 8 hours, though with generally milder effects than 2C-B or DOB.[4]

See also

[edit]

References

[edit]
  1. ^ Standridge RT, Howell HG, Tilson HA, Chamberlain JH, Holava HM, Gylys JA, Partyka RA, Shulgin AT (February 1980). "Phenylalkylamines with potential psychotherapeutic utility. 2. Nuclear substituted 2-amino-1-phenylbutanes". Journal of Medicinal Chemistry. 23 (2): 154–62. doi:10.1021/jm00176a010. PMID 7359529.
  2. ^ Glennon RA, Bondarev ML, Khorana N, Young R, May JA, Hellberg MR, McLaughlin MA, Sharif NA (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): 6034–41. doi:10.1021/jm040082s. PMID 15537358.
  3. ^ Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
  4. ^ Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: Von der Struktur zur Funktion. Nachtschatten Verlag AG. p. 832. ISBN 978-3-03788-700-4.