nabitan

{{Short description|Synthetic cannabinoid}}

{{Drugbox

| verifiedrevid = 421099167

| class = Cannabinoid

| IUPAC_name = 5,5-Dimethyl-8-(3-methyloctan-2-yl)-2-(prop-2-yn-1-yl)-1,3,4,5-tetrahydro-2H-[1]benzopyrano[4,3-c]pyridin-10-yl 4-(piperidin-1-yl)butanoate

| image = Nabitan.svg

| image_class = skin-invert-image

| width = 180

| tradename =

| legal_status =

| routes_of_administration =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 66556-74-9

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

| synonyms = Nabutam, benzopyranoperidine, SP-106, Abbott 40656

| UNII = JO7BOR6B3O

| ATC_prefix = none

| PubChem = 39503

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 36117

| C = 35

| H = 52

| N = 2

| O = 3

| smiles = O=C(Oc2cc(cc1OC(C\3=C(/c12)CN(CC/3)CC#C)(C)C)C(C)C(C)CCCCC)CCCN4CCCCC4

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C35H52N2O3/c1-7-9-11-15-26(3)27(4)28-23-31(39-33(38)16-14-21-36-19-12-10-13-20-36)34-29-25-37(18-8-2)22-17-30(29)35(5,6)40-32(34)24-28/h2,23-24,26-27H,7,9-22,25H2,1,3-6H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = MCVPMHDADNVRKF-UHFFFAOYSA-N

}}

Nabitan (nabutam, benzopyranoperidine, SP-106, Abbott 40656) is a synthetic cannabinoid analog of dronabinol (Δ⁹-tetrahydrocannabinol) and dimethylheptylpyran.Razdan RK. The Total Synthesis of Cannabinoids. Wiley-Interscience 1980 It exhibits antiemetic and analgesic effects, most likely by binding to and activating the CB₁ and CB₂ cannabinoid receptors, and reduced intraocular pressure in animal tests, making it potentially useful in the treatment of glaucoma.{{cite journal | vauthors = Razdan RK, Howes JF | title = Drugs related to tetrahydrocannabinol | journal = Medicinal Research Reviews | year = 1983 | volume = 3 | issue = 2 | pages = 119–46 | doi = 10.1002/med.2610030203 | pmid = 6134882 | s2cid = 31313909 }}

Nabitan has the advantage of being water-soluble, unlike most cannabinoid derivatives, and was researched for potential use as an analgesic or sedative,{{cite journal | vauthors = Archer RA | title = The cannabinoids: therapeutic potentials | journal = Annual Reports in Medicinal Chemistry | year = 1974 | volume = 9 | pages = 253–9 | doi = 10.1016/s0065-7743(08)61448-7 | pmid = 12307093 }} although it was never developed for clinical use and is not currently used in medicine, as dronabinol or nabilone were felt to be more useful. However, it is sometimes used in research into the potential therapeutic applications of cannabinoids.