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Changing short description from "Chemical compound" to "Synthetic cannabinoid"
 
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{{Short description|Synthetic cannabinoid}}
{{Drugbox| verifiedrevid = 400320941
{{Drugbox
|
| verifiedrevid = 421099167
|IUPAC_name = (-)-8-(1,2-Dimethylheptyl)-1,3,4,5-tetrahydro-5,5-dimethyl-2-(2-propynyl) -2H-(1)benzopyrano(4,3-c)pyridin-10-yl 1-piperidinebutyrate
| IUPAC_name = 5,5-Dimethyl-8-(3-methyloctan-2-yl)-2-(prop-2-yn-1-yl)-1,3,4,5-tetrahydro-2''H''-[1]benzopyrano[4,3-''c'']pyridin-10-yl 4-(piperidin-1-yl)butanoate
| image = Nabitan.svg
| image = Nabitan.svg
| width= 180
| width = 180

<!--Clinical data-->
| tradename =
| legal_status =
| routes_of_administration =

<!--Pharmacokinetic data-->
| metabolism =
| elimination_half-life =
| excretion =

<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 66556-74-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = JO7BOR6B3O
| ATC_prefix = none
| PubChem = 39503
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 36117
| ChemSpiderID = 36117

| InChI = 1/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
<!--Chemical data-->
| InChIKey = MCVPMHDADNVRKF-UHFFFAOYAU
| 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
| 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_Ref = {{stdinchicite|correct|chemspider}}
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = MCVPMHDADNVRKF-UHFFFAOYSA-N
| StdInChIKey = MCVPMHDADNVRKF-UHFFFAOYSA-N
| CAS_number= 66556-74-9
| ATC_prefix= none
| ATC_suffix=
| PubChem= 39503
| DrugBank=
| C=35 | H=52 | N=2 | O=3
| molecular_weight = 548.799 g/mol
| bioavailability=
| metabolism =
| elimination_half-life=
| excretion =
| pregnancy_category =
| legal_status =
| routes_of_administration=
}}
}}
'''Nabitan''' ('''Nabutam''', '''Benzopyranoperidine''', '''SP-106''', '''Abbott 40656''') is a [[Chemical synthesis|synthetic]] [[cannabinoid]] [[Analog (chemistry)|analog]] of [[dronabinol]] (Marinol) and [[dimethylheptylpyran]].<ref>Razdan RK. The Total Synthesis of Cannabinoids. Wiley-Interscience 1980</ref> It exhibits [[antiemetic]] and [[analgesic]] effects, most likely by binding to and activating the CB<sub>1</sub> and CB<sub>2</sub> [[cannabinoid receptor]]s, and reduced [[intraocular pressure]] in animal tests, making it potentially useful in the treatment of [[glaucoma]].<ref>{{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 }}</ref>


Nabitan has the advantage of being water-soluble, unlike most cannabinoid derivatives, and was researched for potential use as an analgesic or [[sedative]],<ref>{{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 }}</ref> 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.
'''Nabitan''' ('''Nabutam''', '''Benzopyranoperidine''', '''SP-106''', '''Abbott 40656''') is a [[Chemical synthesis|synthetic]] [[cannabinoid]] [[Analog (chemistry)|analog]] of [[dronabinol]] (Marinol).<ref> Razdan RK. The Total Synthesis of Cannabinoids. Wiley-Interscience 1980 </ref> It exhibits [[antiemetic]] and [[analgesic]] effects, most likely by binding to and activating the CB<sub>1</sub> and CB<sub>2</sub> [[cannabinoid receptor]]s, and reduced [[intraocular pressure]] in animal tests, making it potentially useful in the treatment of [[glaucoma]].<ref>Razdan RK, Howes JF. "Drugs related to tetrahydrocannabinol." ''Medicinal Research Reviews'' 1983; 3(2):119-146. PMID 6134882</ref>


== See also ==
Nabitan has the advantage of being water soluble unlike most cannabinoid derivatives, and was researched for potential use as an analgesic or [[sedative]],<ref>Archer RA. "The cannabinoids: therapeutic potentials." ''Annual Reports in Medicinal Chemistry'' 1974; 9: 253-259. PMID 12307093</ref> 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.
* [[A-40174]] (SP-1)

* [[A-41988]]
{{cannabinoid-stub}}
* [[Dimethylheptylpyran]]
* [[Menabitan]]


== References ==
== References ==
{{Reflist}}
<references />


[[de:Nabitan]]
{{Cannabinoids}}
{{Cannabinoids}}
{{Hallucinogens}}
{{Cannabinoidergics}}


[[Category:Propargyl compounds]]

[[Category:Carboxylate esters]]
[[Category:Cannabinoids]]
[[Category:Cannabinoids]]
[[Category:Chromenes]]
[[Category:Benzopyrans]]
[[Category:Alkynes]]
[[Category:Nitrogen heterocycles]]
[[Category:Butyrates]]
[[Category:Oxygen heterocycles]]
[[Category:Piperidines]]
[[Category:Heterocyclic compounds with 3 rings]]
[[Category:1-Piperidinyl compounds]]

{{cannabinoid-stub}}