Cilobamine

{{Short description|Chemical compound}}

{{Infobox drug

| IUPAC_name = (2R,3R)-2-(3,4-Dichlorophenyl)-3-[(1-methylethyl)amino]bicyclo[2.2.2]octan-2-ol

| image = Cilobamine clear.svg

| image_class = skin-invert-image

| width = 200

| tradename =

| pregnancy_AU =

| pregnancy_US =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| CAS_number = 69429-84-1

| ATC_prefix = none

| PubChem = 299379

| ChemSpiderID = 8557262

| ChEMBL = 2106470

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 067U1T4S30

| C=17 | H=23 | Cl=2 | N=1 | O=1

| smiles = Clc1ccc(cc1Cl)[C@@]3(O)[C@H](NC(C)C)C2CCC3CC2

}}

Cilobamine is a drug which acts as a norepinephrine-dopamine reuptake inhibitor (NDRI) and has stimulant and antidepressant effects.{{cite journal | vauthors = Leeson GA, Shaath ZA, Biedenbach SA, Yarrington JT, Okerholm RA | title = Dose related induction of the drug metabolizing enzymes of rat liver by cilobamine | journal = Fundamental and Applied Toxicology | volume = 4 | issue = 2 Pt 1 | pages = 261–9 | date = April 1984 | pmid = 6724198 | doi = 10.1016/0272-0590(84)90127-1 }}{{Cite journal | vauthors = Wager S, Quitkin F, Stewart J, McGrath P, Harrison W, Markowitz J, Tricamo E | title = Cilobamine in the treatment of atypical depression | journal = Human Psychopharmacology: Clinical and Experimental | year = 1988 | pages = 201–205| volume = 3 | issue = 3 | doi = 10.1002/hup.470030308 | s2cid = 145253439 }}

It can clearly be seen that the structure is based on dichloroisoprenaline that has been fused onto the bicycloalkane scaffold.