4C-B: Difference between revisions

4C-B
Names
	Preferred IUPAC name 1-(4-Bromo-2,5-dimethoxyphenyl)butan-2-amine
	Other names 4C-DOB, DOB-B
Identifiers
CAS Number	69294-23-1;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL365711;
ChemSpider	23256805;
PubChem CID	12140147;
CompTox Dashboard (EPA)	DTXSID101336665 ;
	InChI 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;
	SMILES CCC(CC1=CC(=C(C=C1OC)Br)OC)N;
Properties
Chemical formula	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). Infobox references

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Latest revision as of 18:32, 30 May 2024

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-HT_2A receptor partial agonist with a K_i 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]

References

^ 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.
^ 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.
^ Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
^ Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: Von der Struktur zur Funktion. Nachtschatten Verlag AG. p. 832. ISBN 978-3-03788-700-4.

This psychoactive drug-related article is a stub. You can help Wikipedia by expanding it.

[pmid7359529-1] 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.

[pmid15537358-2] 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.

[Trachsel-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.

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@@ Line 1: / Line 1: @@
 {{chembox
 | 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
 |Section1={{Chembox Identifiers
@@ Line 8: / Line 8: @@
 | 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
 | CASNo = 69294-23-1
+| ChEMBL = 365711
 | PubChem = 12140147
 | SMILES = CCC(CC1=CC(=C(C=C1OC)Br)OC)N
@@ Line 20: / Line 21: @@
 | Appearance =
 | Density =
-| MeltingPt = 204-206
+| MeltingPt = 204-206 °C
 | BoilingPt =
 | Solubility = }}
@@ Line 29: / Line 30: @@
 }}
-'''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 ==
+* [[4C-T-2]]
 * [[Ariadne (psychedelic)]]
 * [[Phenethylamine]]
 * [[Psychedelics, dissociatives and deliriants]]
+* [[ZC-B]]
 ==References==
 {{Reflist}}
+{{Hallucinogenic phenethylamines}}
 [[Category:Substituted amphetamines]]