4C-B

{{chembox

| Name = 4C-B

| ImageFile1 = 4C-B Structure.svg

| PIN = 1-(4-Bromo-2,5-dimethoxyphenyl)butan-2-amine

| OtherNames = 4C-DOB, DOB-B

|Section1={{Chembox Identifiers

| ChemSpiderID = 23256805

| 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

}}

|Section2={{Chembox Properties

| C=12

| H=18

| Br=1

| N=1

| O=2

| Appearance =

| Density =

| MeltingPt = 204-206 °C

| BoilingPt =

| Solubility = }}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt = }}

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4C-B (also known as 4C-DOB or DOB-B) is a lesser-known psychedelic drug of the phenethylamine, phenylisobutylamine, and 4C families related to 2C-B and DOB.{{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 }} It is a reasonably potent 5-HT_2A receptor partial agonist with a K_i of 7.6{{nbsp}}nM, but has relatively low efficacy (15% relative to 5-HT).{{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 }} It is briefly mentioned in Alexander Shulgin's book PiHKAL (Phenethylamines i Have Known And Loved) but was never tested by him,{{CitePiHKAL|name-list-style = vanc }} however it has subsequently been tested by Daniel Trachsel and colleagues and was found to be active in a dose range of 50 to 80{{nbsp}}mg with a duration of around 8{{nbsp}}hours, though with generally milder effects than 2C-B or DOB.{{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}}