tandamine

{{Short description|Chemical compound}}

{{Drugbox

| verifiedrevid = 448239290

| IUPAC_name = 2-(9-ethyl-1-methyl-3,4-dihydrothiopyrano[3,4-b]indol-1-yl)-N,N-dimethylethanamine

| image = Tandamine.svg

| image_class = skin-invert-image

| tradename =

| pregnancy_category =

| legal_status =

| routes_of_administration =

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| index2_label = HCl

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 42408-80-0

| CAS_number2_Ref = {{cascite|correct|CAS}}

| CAS_number2 = 58167-78-5

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

| UNII = 6L5FH5A43E

| UNII2_Ref = {{fdacite|correct|FDA}}

| UNII2 = 7516K9UGUG

| ATC_prefix = none

| ATC_suffix =

| PubChem = 39187

| ChemSpiderID = 35851

| C=18 | H=26 | N=2 | S=1

| smiles = CCn3c1ccccc1c2CCSC(C)(CCN(C)C)c23

| StdInChI = 1S/C18H26N2S/c1-5-20-16-9-7-6-8-14(16)15-10-13-21-18(2,17(15)20)11-12-19(3)4/h6-9H,5,10-13H2,1-4H3

| StdInChIKey = BRPOADLGOFPKKJ-UHFFFAOYSA-N

}}

Tandamine is a selective norepinephrine reuptake inhibitor with a tricyclic structure.{{cite journal | vauthors = Lippmann W, Pugsley TA | title = The effects of tandamine, a new potential antidepressant agent, on biogenic amine uptake mechanisms and related activities | journal = Biochemical Pharmacology | volume = 25 | issue = 10 | pages = 1179–1186 | date = May 1976 | pmid = 1084746 | doi = 10.1016/0006-2952(76)90366-X }}{{cite journal | vauthors = Ehsanullah RS, Ghose K, Kirby MJ, Turner P, Witts D | title = Clinical pharmacological studies of tandamine, a potential antidepressive drug | journal = Psychopharmacology | volume = 52 | issue = 1 | pages = 73–77 | date = March 1977 | pmid = 403562 | doi = 10.1007/BF00426603 | s2cid = 23960347 }}{{cite journal | vauthors = Pugsley TA, Lippmann W | title = Effect of acute and chronic treatment of tandamine, a new heterocyclic antidepressant, on biogenic amine metabolism and related activities | journal = Naunyn-Schmiedeberg's Archives of Pharmacology | volume = 308 | issue = 3 | pages = 239–247 | date = September 1979 | pmid = 503251 | doi = 10.1007/BF00501388 | s2cid = 23533861 }} It was developed in the 1970s as an antidepressant but was never commercialized. Tandamine is analogous to pirandamine, which, instead, acts as a selective serotonin reuptake inhibitor (SSRI).{{cite journal | vauthors = Pugsley T, Lippmann W | title = Effects of tandamine and pirandamine, new potential antidepressants, on the brain uptake of norepinephrine and 5-hydroxytryptamine and related activities | journal = Psychopharmacology | volume = 47 | issue = 1 | pages = 33–41 | date = May 1976 | pmid = 1085452 | doi = 10.1007/BF00428698 | s2cid = 8354739 }}{{cite journal | vauthors = Lippmann W, Seethaler K | title = Effects of tandamine and pirandamine, selective blockers of biogenic amine uptake mechanisms, on gastric acid secretion and ulcer formation in the rat | journal = Life Sciences | volume = 20 | issue = 8 | pages = 1393–1400 | date = April 1977 | pmid = 853871 | doi = 10.1016/0024-3205(77)90367-8 }}

The exact identical same structure, although this time changing the thioether to a methylene group revealed a strongest compound of the series called AY 24614.{{cite journal | vauthors = Asselin AA, Humber LG, Komlossy J | title = Cycloalkanoindoles. 2. 1-Alkyl-1,2,3,4-tetrahydrocarbazole-1-ethanamines and related compounds. Potential antidepressants | journal = Journal of Medicinal Chemistry | volume = 19 | issue = 6 | pages = 792–797 | date = June 1976 | pmid = 950648 | doi = 10.1021/jm00228a011 }}